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【结 构 式】

【分子编号】18304

【品名】3,4-Dimethoxybenzaldehyde; Veratraldehyde

【CA登记号】120-14-9

【 分 子 式 】C9H10O3

【 分 子 量 】166.1766

【元素组成】C 65.05% H 6.07% O 28.88%
与该中间体有关的原料药合成路线共 19 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9合成路线10合成路线11合成路线12合成路线13合成路线14合成路线15合成路线16合成路线17合成路线18合成路线19

合成路线1

该中间体在本合成路线中的序号：(I)

3,4-Dimethoxybenzaldehyde (I) is treated with 1,3-propanedithiol (II) to give 2-(3,4-dimethoxyphenyl)-m-dithiane (III), the oxidation product of which (IV) is reacted with N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropanamine chloride (V) in the presence of a base.

参考文献 中间体
合成目标
【1】 Ramuz, H.; DE 2460593 .
【2】 Ramuz, H.; A new Ca2+ antagonist, Ro-111781 and its metabolites. Synthesis and physicochemical properties. Arzneim-Forsch Drug Res 1978, 28, 11, 2048.
【3】 Koch, H.; Ro-11,1781. Drugs Fut 1979, 4, 2, 122.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 29729 1,3-propanedithiol; 3-sulfanylpropylhydrosulfide 109-80-8 C3H8S2 详情 详情
(III) 39515 2-(3,4-dimethoxyphenyl)-1,3-dithiane; 4-(1,3-dithian-2-yl)-2-methoxyphenyl methyl ether C12H16O2S2 详情 详情
(IV) 39516 2-(3,4-dimethoxyphenyl)-1lambda(6),3lambda(6)-dithiane-1,1,3,3-tetrone C12H16O6S2 详情 详情
(V) 29986 3-chloro-N-(3,4-dimethoxyphenethyl)-N-methyl-1-propanamine; N-(3-chloropropyl)-N-(3,4-dimethoxyphenethyl)-N-methylamine C14H22ClNO2 详情 详情

合成路线2

该中间体在本合成路线中的序号：(I)

The synthesis of nitidine chloride was first reported in 1973. The procedure was based on the synthesis of dihydronitidine, which involves hydrocyanation of the corresponding chalcone, followed by hydrolysis, reduction and cyclization to the 2-aryl tetralone. Leukart reaction of the tetralone followed by ring closure with phosphorus oxychloride and catalytic dehydrogenation yields the benzo[c]phenanthridine nucleus. Methylation and quarternization with methyl sulfate followed by anion exchange with sodium chloride forms the chloride salt of the desired compound. Several other syntheses of nitidine chloride have also been reported. These include: a) synthesis of the intermediates by a different route; b) photocyclization of bromobenzamide from 5-aminonaphthalene to phenanthridine; and c) condensation of homophthalic anhydride and the Schiff base to form the 3-arylisoquinoline. Many analogues of nitidine chloride, including fagaronine. The tetramethoxy analogue, the indenoisoquinoline derivative, etc., possess significant antineoplastic activity.

参考文献 中间体
合成目标
【1】 Miyadera, T.; et al.; J Heterocycl Chem 1973, 10, 6, 85-88.
【2】 Pabbathi, V.K.; et al.; J Heterocycl Chem 1973, 10, 2, 31-33.
【3】 Okamoto, T.; et al.; Tetrahedron Lett 1974, 297, 2, 2269-2270.
【4】 Muramatsu, I.; Ahmed, M.; Ohnuki, T.; Nagatomo, T.; Futabayashi, Y.; Ishiguro, M.; J Heterocycl Chem 1981, 18, 21, 223-232.
【5】 Gupta, Y.K.; Sharma, M.; J Org Chem 1978, 43, 21, 286-288.
【6】 May, H.-J.; J Chem Soc 1959, 30, 10, 4010-4012.
【7】 Caldwell, J.; Glowka, F.K.; J Chem Soc - Perkins Trans I 1977, 14, 9, 2324-2328.
【8】 Cheng, C.C.; Zee-Chenh, R.K.-Y.; Preparation and antileukemic activity of some alkoxybenzo[c]phenanthridinium salts and corresponding dihydro derivatives. J Med Chem 1975, 18, 1, 66-71.
【9】 Cushman, M.; Mohan, P.; Smith, E.C.R.; Synthesis and biological activity of structural analogues of the anticancer benzophenanthridine alkaloid nitidine chloride. J Med Chem 1984, 27, 4, 544-547.
【10】 Zee-Cheng, R.K.-Y.; Cheng, C.C.; Nitidine Chloride. Drugs Fut 1985, 10, 2, 124.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 28953 1-(1,3-benzodioxol-5-yl)-1-ethanone 3162-29-6 C9H8O3 详情 详情
(III) 28954 (E)-1-(1,3-benzodioxol-5-yl)-3-(3,4-dimethoxyphenyl)-2-propen-1-one C18H16O5 详情 详情
(IV) 28955 4-(1,3-benzodioxol-5-yl)-2-(3,4-dimethoxyphenyl)-4-oxobutanenitrile C19H17NO5 详情 详情
(V) 28956 4-(1,3-benzodioxol-5-yl)-2-(3,4-dimethoxyphenyl)-4-oxobutyric acid C19H18O7 详情 详情
(VI) 28957 4-(1,3-benzodioxol-5-yl)-2-(3,4-dimethoxyphenyl)butyric acid C19H20O6 详情 详情
(VII) 28958 6-(3,4-dimethoxyphenyl)-7,8-dihydronaphtho[2,3-d][1,3]dioxol-5(6H)-one C19H18O5 详情 详情
(VIII) 28959 6-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxol-5-ylformamide C20H21NO5 详情 详情
(IX) 28960 2,3-dimethoxy-4b,5,6,11b-tetrahydro[1,3]benzodioxolo[5,6-c]phenanthridine C20H19NO4 详情 详情
(X) 28961 2,3-dimethoxy[1,3]benzodioxolo[5,6-c]phenanthridine C20H15NO4 详情 详情
(XI) 28962 2,3-dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium (sulfonatooxy)methane C22H21NO8S 详情 详情

合成路线3

该中间体在本合成路线中的序号：(I)

The condensation of 3,4-dimethoxybenzaldehyde (I) with glycine (II) by means of KOH in hot methanol gives racemic threo-3-(3,4-dimethoxyphenyl)serine (III), which is acylated with N-(ethoxycarbonyl)phthalimide (IV) by means of Na2CO3 in water yielding the corresponding N-phthaloyl derivative (V). The reaction of (V) with AlCl3 and ethyl mercaptan in dichloromethane affords N-phthaloyl-3-(3,4-dihydroxyphenyl)serine (VI), which is deprotected with hydrazine in refluxing ethanol to racemic threo-3-(3,4-dihydroxyphenyl)serine (VII). The resolution of the racemic form (VII) is performed through its benzyloxy derivative.

参考文献 中间体
合成目标
【1】 Ohashi, N.; Nagata, S.; Ishimuzi, K.; Katsube, J. (Sumitomo Pharmaceuticals Co., Ltd.); Process for the production of optically active thr. EP 0024210; US 4319040 .
【2】 Ohashi, N.; Nagata, S.; Ishizumi, K. (Sumitomo Pharmaceuticals Co., Ltd.); Process for producing 3-(3,4-dihydroxyphenyl)serin. EP 0128684; US 4562263 .
【3】 Castaner, J.; Prous, J.; L-threo-DOPS. Drugs Fut 1987, 12, 5, 433.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 20436 glycine 56-40-6 C2H5NO2 详情 详情
(III) 22983 3-hydroxy-3,4-dimethoxyphenylalanine C11H15NO5 详情 详情
(IV) 10283 ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide 22509-74-6 C11H9NO4 详情 详情
(V) 22985 3-(3,4-dimethoxyphenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxypropionic acid C19H17NO7 详情 详情
(VI) 22986 3-(3,4-dihydroxyphenyl)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxypropionic acid C17H13NO7 详情 详情

合成路线4

该中间体在本合成路线中的序号：

6-Hydroxy-2(1H)-quinolinone (I) is alkylated with epichlorohydrin in the presence of K2CO3 in MeOH to afford 6-(2,3-epoxypropoxy)-2(1H)-quinolinone (II). Ring opening of the epoxide (II) with 3,4-dimethoxybenzylamine gives OPC-18790. This compound is also obtained by the reductive alkylation of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone (III) with 3,4-dimethoxybenzaldehyde.

参考文献 中间体
合成目标
【1】 Sumida, T.; Fujioka, T.; Teramoto, S.; Tominaga, M.; Yabuuchi, Y.; Mori, T.; Hosokawa, T.; Novel positive inotropic agents; synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives. J Med Chem 1992, 35, 20, 3607-12.
【2】 Fujioka, T.; OPC-18790. Drugs Fut 1993, 18, 12, 1114.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
13920 (3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine 5763-61-1 C9H13NO2 详情 详情
18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(I) 13913 6-Hydroxy-2(1H)-quinolinone C9H7NO2 详情 详情
(II) 13914 6-(2-Oxiranylmethoxy)-2(1H)-quinolinone C12H11NO3 详情 详情
(III) 13915 6-(3-Amino-2-hydroxypropoxy)-2(1H)-quinolinone C12H14N2O3 详情 详情

合成路线5

该中间体在本合成路线中的序号：(V)

Reaction of 3-furancarboxaldehyde (I) with potassium cyanide in the presence of tert-butyldimethylsilyl chloride and ZnI2 gave the O-silylated cyanohydrin (II). Addition of 2(5H)-furanone (III) to the lithium anion of (II), followed by addition of 3,4-dimethoxybenzaldehyde (V) to the intermediate (IV), yielded adduct (VI). Subsequent acid cyclization of (VI) by means of trifluoroacetic acid or methanesulfonic acid provided the tricyclic derivative (VII) as a diastereomeric mixture. Desilylation of (VII) with concomitant cyanide elimination using either tetrabutylammonium fluoride at low temperature or aqueous ammonium fluoride gave rise to ketone (VIII). This was then epimerized to the title compound by treatment with triethylamine in boiling toluene. Alternatively, desilylation of (VII) with tetrabutylammonium fluoride at room temperature provided directly the title diastereoisomer.

参考文献 中间体
合成目标
【1】 Iwasaki, T.; Sugiura, M.; Matsuoka, Y.; Matsumoto, M.; Kitamura, K. (Tanabe Seiyaku Co., Ltd.); Biphenyl derivs.. EP 0386778; JP 1990235884; US 5066669 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 47247 3-Furaldehyde 498-60-2 C5H4O2 详情 详情
(II) 47248 2-[[tert-butyl(dimethyl)silyl]oxy]-2-(3-furyl)acetonitrile C12H19NO2Si 详情 详情
(III) 19267 2(5H)-furanone；furan-2(5H)-one；2-Buten-1,4-olide 497-23-4 C4H4O2 详情 详情
(IV) 47249 　 C16H22LiNO4Si 详情 详情
(V) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(VI) 47250 2-[[tert-butyl(dimethyl)silyl]oxy]-2-[4-[(3,4-dimethoxyphenyl)(hydroxy)methyl]-5-oxotetrahydro-3-furanyl]-2-(3-furyl)acetonitrile C25H33NO7Si 详情 详情
(VII) 47251 (4S,4aR,7aR,8R)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-(3,4-dimethoxyphenyl)-7-oxo-4,4a,5,7,7a,8-hexahydrofuro[2,3-f][2]benzofuran-4-carbonitrile C25H31NO6Si 详情 详情
(VIII) 47252 (4R,4aR,7aR,8R)-4-[[tert-butyl(dimethyl)silyl]oxy]-8-(3,4-dimethoxyphenyl)-7-oxo-4,4a,5,7,7a,8-hexahydrofuro[2,3-f][2]benzofuran-4-carbonitrile C25H31NO6Si 详情 详情
(IX) 47253 (4aR,7aR,8R)-8-(3,4-dimethoxyphenyl)-4a,5,7a,8-tetrahydrofuro[2,3-f][2]benzofuran-4,7-dione C18H16O6 详情 详情

合成路线6

该中间体在本合成路线中的序号：(I)

Amino alcohol (III) was prepared from veratraldehyde (I) by addition of cyanotrimethylsilane, followed by borane reduction of the resultant cyanohydrin (II). Reductive condensation of amine (III) with 2,3-dimethoxybenzaldehyde (IV) gave the secondary amine (V). This was cyclized to the tetrahydroisoquinoline (VI) under acidic conditions. Resolution of the racemic (VI) by means of dibenzoyltartaric acid furnished the desired (S)-amine, which was further acylated with Ac2O to yield the chiral amide (VII). Demethylation of (VII) with boron tribromide afforded the tetrahydroxy compound (VIII). Finally, acetamide hydrolysis under acidic conditions yielded the title compound.

参考文献 中间体
合成目标
【1】 Anan, H.; Tanaka, A.; Tsuzuki, R.; Yokota, M.; Yatsu, T.; Honda, K.; Asano, M.; Fujita, S.; Furuya, T.; Fujikura, T.; Synthesis, resolution, and renal vasodilation activity of novel DA1 agonists: 4-(3,4-Dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline derivatives. Chem Pharm Bull 1991, 39, 11, 2910.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 63099 2-(3,4-dimethoxyphenyl)-2-[(trimethylsilyl)oxy]acetonitrile C13H19NO3Si 详情 详情
(III) 63100 2-amino-1-(3,4-dimethoxyphenyl)-1-ethanol C10H15NO3 详情 详情
(IV) 17615 2,3-Dimethoxybenzaldehyde 86-51-1 C9H10O3 详情 详情
(V) 63101 2-[(2,3-dimethoxybenzyl)amino]-1-(3,4-dimethoxyphenyl)-1-ethanol C19H25NO5 详情 详情
(VI) 63102 4-(3,4-dimethoxyphenyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 4-(3,4-dimethoxyphenyl)-7-methoxy-1,2,3,4-tetrahydro-8-isoquinolinyl methyl ether C19H23NO4 详情 详情
(VII) 63103 1-[(4R)-4-(3,4-dimethoxyphenyl)-7,8-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone C21H25NO5 详情 详情
(VIII) 63104 1-[(4R)-4-(3,4-dihydroxyphenyl)-7,8-dihydroxy-3,4-dihydro-2(1H)-isoquinolinyl]-1-ethanone C17H17NO5 详情 详情

合成路线7

该中间体在本合成路线中的序号：(I)

The bromination of 3,4-dimethoxybenzaldehyde (I) with Br2 in methanol gives the 6-bromo-3,4-dimethoxybenzaldehyde (II), which is regioselectively demethylated with conc. H2SO4 yielding 6-bromo-3-hydroxy-4-methoxybenzaldehyde (III). The reductocondensation of (III) with 2-(4-hydroxyphenyl)ethylamine (IV) by means of NaBH4 in ethanol affords the secondary amine (V), which is formylated with ethyl formate and formic acid in dioxane furnishing the formamide (VI). The oxidative cyclization of (VI) by means of potassium ferricyanide and K2CO3 in toluene/water gives the (+/-)-bromoformylnarwedine (VII), which is protected with propyleneglycol (VIII) and TsOH in hot toluene yielding the ketal (IX). The reduction of the formyl group of (IX) with LiAlH4 in THF affords racemic narwedine (X), which is submitted to a crystallization-induced chiral transformation using a catalytic amount of seed crystals of (-)-narwedine in refluxing ethanol containing TEA, an 80% of (-)-narwedine (XI) is obtained. Finally, this compound is stereoselectively reduced to the target compound by means of L-selectride in THF.

参考文献 中间体
合成目标
【1】 Kuenburg, B.; et al.; Development of a pilot scale process for the anti-Alzheimer drug (-)-galanthamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion. Org Process Res Dev 1999, 3, 6, 425.
【2】 Chaplin, D.A.; et al.; A concise, scaleable synthesis of narwedine. Tetrahedron Lett 1997, 38, 45, 7931.
【3】 Czollner, L.; et al.; New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine. Tetrahedron Lett 1998, 39, 15, 2087.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 36481 2-bromo-4,5-dimethoxybenzaldehyde 5392-10-9 C9H9BrO3 详情 详情
(III) 36482 2-bromo-5-hydroxy-4-methoxybenzaldehyde 2973-59-3 C8H7BrO3 详情 详情
(IV) 19988 4-(2-Aminoethyl)phenol; Tyramine 51-67-2 C8H11NO 详情 详情
(V) 36483 4-bromo-5-[[(4-hydroxyphenethyl)amino]methyl]-2-methoxyphenol C16H18BrNO3 详情 详情
(VI) 36484 2-bromo-5-hydroxy-4-methoxybenzyl(4-hydroxyphenethyl)formamide C17H18BrNO4 详情 详情
(VII) 36689 1-bromo-3-methoxy-6-oxo-5,6,9,10-tetrahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-11(12H)-carbaldehyde C17H16BrNO4 详情 详情
(VIII) 36692 1,2-Propanediol; 1,2-Propylene glycol; 1,2-Dihydroxypropane; Monopropylene glycol; (+/-)-1,2-Propanediol; (+/-)-Propylene glycol; Propan-1,2-diol; propylene glycol 57-55-6 C3H8O2 详情 详情
(IX) 36690 　 C20H22BrNO5 详情 详情
(X) 26837 3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-one C17H19NO3 详情 详情
(XI) 36691 (4aS,8aS)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-one C17H19NO3 详情 详情

合成路线8

该中间体在本合成路线中的序号：(I)

Condensation of 3,4-dimethoxybenzaldehyde (I) with malonic acid (II) in the presence of ammonium acetate afforded 3-amino-arylpropionic acid (III), which was esterified with MeOH and SOCl2 to give (IV). Finally, condensation with tetrafluorophthalic anhydride (V) in refluxing AcOH provided the target phthalimide.

参考文献 中间体
合成目标
【1】 Muller, G.W.; Shire, M.G.; Wong, L.M.; Corral, L.G.; Patterson, R.T.; Chen, Y.; Stirling, D.I.; Thalidomide analogs and PDE4 inhibition. Bioorg Med Chem Lett 1998, 8, 19, 2669.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(III) 18306 3-(3,4-dimethoxyphenyl)-beta-alanine C11H15NO4 详情 详情
(IV) 18307 methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride C12H18ClNO4 详情 详情
(V) 18308 4,5,6,7-tetrafluoro-2-benzofuran-1,3-dione; Tetrafluorophthalic anhydride 652-12-0 C8F4O3 详情 详情

合成路线9

该中间体在本合成路线中的序号：(II)

Reductive alkylation of trans-1,2-cyclohexanediamine (I) with veratraldehyde (II) in the presence of NaBH4 afforded the corresponding bis-(benzylamino)cyclohexane derivative (III). This was then alkylated with solanesyl bromide (IV) in THF to furnish the title compound

参考文献 中间体
合成目标
【1】 Inomata, K.; Takahashi, T.; Inoue, H.; Taniuchi, M.; Yamazaki, H.; Suzuki, M.; Takazawa, T.; Kawamura, K.; Oshida, N.; Ikemoto, H.; Kishie, T. (Nisshin Seifun Group Inc.); Isoprene derivs.. EP 0787716; JP 1997268162 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 23788 (1S,2S)-2-aminocyclohexylamine; (1S,2S)-1,2-cyclohexanediamine 21436-03-3 C6H14N2 详情 详情
(II) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(III) 60503 (1R,2R)-N~1~,N~2~-bis(3,4-dimethoxybenzyl)-1,2-cyclohexanediamine; N-(3,4-dimethoxybenzyl)-N-{(1R,2R)-2-[(3,4-dimethoxybenzyl)amino]cyclohexyl}amine C24H34N2O4 详情 详情
(IV) 60504 (2E,6E,10E,14E,18E,22E,26E,30E)-1-bromo-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaene C45H73Br 详情 详情

合成路线10

该中间体在本合成路线中的序号：(XII)

Protection of 3,4,5-trimethoxybenzaldehyde (IX) with ethylene glycol (X) affords acetal (XI). After lithiation of (XI) by means of butyllithium, addition to veratraldehyde (XII) furnishes carbinol (XIII). Finally, cyclization of hydroxy acetal (XIII) with alkyne (VIII) under acidic conditions provides the title naphthol derivative.

参考文献 中间体
合成目标
【1】 Mori, S.; Takechi, S.; Kida, S.; Mizui, T.; Ichihashi, T. (Shionogi & Co. Ltd.); Lignan analog, production thereof, and hypolipidemic drug. EP 0597107; EP 0701991; JP 1993310634; US 5731455; WO 9308155 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 57432 methyl 6-ethyl-4-oxo-2-octynoate C11H16O3 详情 详情
(IX) 11136 3,4,5-Trimethoxybenzaldehyde 86-81-7 C10H12O4 详情 详情
(X) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(XI) 57434 2-(3,4,5-trimethoxyphenyl)-1,3-dioxolane; 4-(1,3-dioxolan-2-yl)-2,6-dimethoxyphenyl methyl ether C12H16O5 详情 详情
(XII) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(XIII) 57435 (3,4-dimethoxyphenyl)[6-(1,3-dioxolan-2-yl)-2,3,4-trimethoxyphenyl]methanol C21H26O8 详情 详情

合成路线11

该中间体在本合成路线中的序号：(IV)

A different synthetic strategy requires the precursor phthalide derivative (V), which is prepared by two related ways. 3,4,5-Trimethoxybenzoyl chloride (I) is condensed with 2-amino-2-methyl-1-propanol (II), and the resultant hydroxy amide is further cyclized with SOCl2 to the oxazoline (III). Lithiation of (III), followed by addition to veratraldehyde (IV) and acidic oxazoline hydrolysis, leads to the target lactone (V). Alternatively, isobenzofuranone (V) is obtained by direct condensation between trimethoxybenzoic acid (VI) and veratraldehyde (IV) in the presence of polyphosphoric acid.

参考文献 中间体
合成目标
【1】 Mori, S.; et al.; Convergent synthesis of S-8921, a new potent hypocholesterolemic arylnapththalene lignan analog. Tetrahedron Lett 1999, 40, 6, 1165.
【2】 Mori, S.; Takechi, S.; Kida, S. (Shionogi & Co. Ltd.); Process for producing lignan cpd.. EP 0646570; WO 9424087 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 13571 3,4,5Ttrimethoxybenzoyl chloride 4521-61-3 C10H11ClO4 详情 详情
(II) 21513 2-amino-2-methyl-1-propanol；Karl Fischer;2-Amino-2-methyl-propan-1-ol；2-amino-2-methyl-1-propanol 124-68-5 C4H11NO 详情 详情
(III) 57442 4-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)-2,6-dimethoxyphenyl methyl ether; 4,4-dimethyl-2-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,3-oxazole C14H19NO4 详情 详情
(IV) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(V) 57443 3-(3,4-dimethoxyphenyl)-4,5,6-trimethoxy-2-benzofuran-1(3H)-one C19H20O7 详情 详情
(VI) 32225 3,4,5-trimethoxybenzoic acid 118-41-2 C10H12O5 详情 详情

合成路线12

该中间体在本合成路线中的序号：(I)

Reduction of 3,4-dimethoxybenzaldehyde (I) with NaBH4 provided benzyl alcohol (II). After conversion of (II) to the benzyl chloride (III) using SOCl2, its reaction with PPh3 (IV) in refluxing xylene afforded phosphonium salt (V). Subsequent Wittig reaction of the corresponding ylide with 4,4-(ethylenedioxy)cyclohexanone (VI) produced the benzylidene derivative (VII), which was reduced to benzyl compound (VIII) by catalytic hydrogenation over Pd/C. The ketal protecting group of (VIII) was then removed by acid hydrolysis to yield cyclohexanone (IX). Finally, the target tetrahydroquinazoline was obtained by condensation of (IX) with cyanoguanidine (X) at 180 C.

参考文献 中间体
合成目标
【1】 Papoulis, A.T.; Queener, S.F.; Rosowsky, A.; Forsch, R.A.; Synthesis and antiparasitic and antitumor activity. J Med Chem 1999, 42, 6, 1007.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 23603 (3,4-dimethoxyphenyl)methanol 93-03-8 C9H12O3 详情 详情
(III) 23604 4-(chloromethyl)-2-methoxyphenyl methyl ether; 4-(chloromethyl)-1,2-dimethoxybenzene 7306-46-9 C9H11ClO2 详情 详情
(IV) 23605 trimethylphosphine 594-09-2 C3H9P 详情 详情
(V) 23606 (3,4-dimethoxybenzyl)(trimethyl)phosphonium C12H20O2P 详情 详情
(VI) 11377 1,4-Dioxaspiro[4.5]decan-8-one 4746-97-8 C8H12O3 详情 详情
(VII) 23608 8-(3,4-dimethoxybenzylidene)-1,4-dioxaspiro[4.5]decane; 4-(1,4-dioxaspiro[4.5]dec-8-ylidenemethyl)-2-methoxyphenyl methyl ether C17H22O4 详情 详情
(VIII) 23609 4-(1,4-dioxaspiro[4.5]dec-8-ylmethyl)-2-methoxyphenyl methyl ether; 8-(3,4-dimethoxybenzyl)-1,4-dioxaspiro[4.5]decane C17H24O4 详情 详情
(IX) 23610 4-(3,4-dimethoxybenzyl)cyclohexanone C15H20O3 详情 详情
(X) 23611 N-cyanoguanidine 461-58-5 C2H4N4 详情 详情

合成路线13

该中间体在本合成路线中的序号：(I)

Knoevenagel condensation of 3,4-dimethoxybenzaldehyde (I) with malonic acid produced the cinnamic acid (II), which was further reduced to (III) by catalytic hydrogenation using Pd/C. Conversion of (III) to the corresponding acid chloride (IV), followed by Friedel-Crafts intramolecular cyclization gave the indanone (V). Nitrosation of (V) yielded the oximino derivative (VI), which was subsequently silylated with t-butyldimethylsilyl chloride and imidazole to afford the O-silyl oxime (VII). Reduction of (VII) with borane-dimethyl sulfide complex produced the amino alcohol (VIII). Without isolation, (VIII) was converted to the dipropylamino compound (IX) by reductive alkylation with propionaldehyde and NaBH(OAc)3. Amino alcohol (IX) was finally deoxygenated by means of triethylsilane in the presence of boron trifluoride etherate.

参考文献 中间体
合成目标
【1】 Haadsma-Svensson, S.R.; Cleek, K.A.; Dinh, D.M.; et al.; Dopamine D3 receptor antagonists. 1. Synthesis and structure-activity relationships of 5,6-dimethoxy-N-alkyl- and N-alkylaryl-substituted 2-aminoindans. J Med Chem 2001, 44, 26, 4716.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 28568 (E)-3-(3,4-dimethoxyphenyl)-2-propenoic acid 2316-26-9 C11H12O4 详情 详情
(III) 40182 3-(3,4-dimethoxyphenyl)propionic acid 2107-70-2 C11H14O4 详情 详情
(IV) 56565 3-(3,4-dimethoxyphenyl)propanoyl chloride C11H13ClO3 详情 详情
(V) 13430 5,6-Dimethoxy-1-indanone; 2,3-Dihydro-5,6-dimethoxy-1H-inden-1-one 2107-69-9 C11H12O3 详情 详情
(VI) 27302 5,6-dimethoxy-1H-indene-1,2(3H)-dione 2-oxime C11H11NO4 详情 详情
(VII) 56566 5,6-dimethoxy-1H-indene-1,2(3H)-dione 2-{O-[tert-butyl(dimethyl)silyl]oxime} C17H25NO4Si 详情 详情
(VIII) 56567 2-amino-5,6-dimethoxy-1-indanol C11H15NO3 详情 详情
(IX) 56568 2-(dipropylamino)-5,6-dimethoxy-1-indanol C17H27NO3 详情 详情

合成路线14

该中间体在本合成路线中的序号：(I)

Condensation of veratraldehyde (I) with malonic acid and ammonium acetate in refluxing EtOH afforded 3-amino-3-(3,4-dimethoxyphenyl)propionic acid (II). The N-phthaloyl group was introduced in (II) by treatment with N-carbethoxyphthalimide (III) in the presence of Na2CO3. The resulting phthalimido acid (IV) was converted to the title amide via activation with carbonyl diimidazole, followed by treatment with ammonium hydroxide.

参考文献 中间体
合成目标
【1】 Fernandez-Martinez, E.; et al.; Effects of thalidomide and 3-phthalimido-3-(3,4-dimethoxyphenyl)-propanamide on bile duct obstruction-induced cirrhosis in the rat. Drug Dev Res 2001, 54, 4, 209.
【2】 Muller, G.W.; Shire, M.G.; Wong, L.M.; Corral, L.G.; Patterson, R.T.; Chen, Y.; Stirling, D.I.; Thalidomide analogs and PDE4 inhibition. Bioorg Med Chem Lett 1998, 8, 19, 2669.
【3】 Muller, G.W.; et al.; Structural modifications of thalidomide produce analogs with enhanced tumor necrosis factor inhibitory activity. J Med Chem 1996, 39, 17, 3238.
【4】 Muller, G.W. (Celgene Corp.); Ring closure of N-phthaloylglutamines. EP 1004572; EP 1004580; US 5463063; WO 9501348 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12963 Malonic acid 141-82-2 C3H4O4 详情 详情
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 18306 3-(3,4-dimethoxyphenyl)-beta-alanine C11H15NO4 详情 详情
(III) 10283 ethyl 1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate; N-Carbethoxyphthalimide 22509-74-6 C11H9NO4 详情 详情
(IV) 37235 3-(3,4-dimethoxyphenyl)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propionic acid C19H17NO6 详情 详情

合成路线15

该中间体在本合成路线中的序号：(I)

The intermediate alcohol (VIII) was prepared as shown in Scheme 27060901a: Aldol condensation of 3,4-dimethoxybenzaldehyde (I) with 3-hydroxyacetophenone (II) in the presence of KOH provided chalcone (III), which was hydrogenated over Pd/C to yield the corresponding diarylpropanone (IV). Subsequent alkylation of the phenolic hydroxyl group of (IV) with tert-butyl bromoacetate (V) using NaH in DMF gave ether (VI). Then, enantioselective reduction of ketone by means of (+)-beta-chlorodiisopinocampheylborane (VII) at -20 C furnished the (R)-alcohol (VIII).

参考文献 中间体
合成目标
【1】 Yang, W.; Guo, T.; Keenan, T.P.; Laborde, E.; Holt, D.A. (Ariad Pharmaceuticals Inc.); Synthetic derivs. of rapamycin as multimerizing agents for chimeric proteins with immunophilin-derived domains. JP 2000505475; WO 9731898 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 25331 3-hydroxyacetophenone; 1-(3-hydroxyphenyl)-1-ethanone 121-71-1 C8H8O2 详情 详情
(III) 25332 (E)-3-(3,4-dimethoxyphenyl)-1-(3-hydroxyphenyl)-2-propen-1-one C17H16O4 详情 详情
(IV) 25341 3-(3,4-dimethoxyphenyl)-1-(3-hydroxyphenyl)-1-propanone C17H18O4 详情 详情
(V) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(VI) 25342 tert-butyl 2-[3-[3-(3,4-dimethoxyphenyl)propanoyl]phenoxy]acetate C23H28O6 详情 详情
(VII) 25343 chloro[bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]]borane 112246-73-8 C20H34BCl 详情 详情
(VIII) 25348 tert-butyl 2-[3-[(1R)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl]phenoxy]acetate C23H30O6 详情 详情

合成路线16

该中间体在本合成路线中的序号：(II)

The condensation of 4-benzyloxy-2-hydroxy-6-methoxyacetophenone (I) with 3,4-dimethoxybenzaldehyde (II) by means of KOH in ethanol/water gives the chalcone (III), which is cyclized by means of SeO2 in refluxing isoamyl alcohol to yield the benzopyran (IV). The hydrogenolysis of the benzyl group of (IV) with H2 over Pd/C in chloroform affords the 7-hydroxybenzopyran (V), which is condensed with tert-butyl bromoacetate (VII) by means of CaCO3 in DMF to provide the benzopyranyloxy acetate (VIII). Finally, this compound is deprotected by reaction with p-toluenesulfonic acid in refluxing benzene.

参考文献 中间体
合成目标
【1】 Yoo, M.; Son, M.W.; Kin, I.Y.; Kin, W.B.; Kin, S.H.; Lee, S.D.; Lim, G.J.; Lim, J.I.; Ahn, B.O.; Baik, N.G.; Kin, D.S.; Oh, T.Y.; Ryu, B.K.; Yang, J.S.; Shin, H.C. (Dong-A Pharmaceutical Co., Ltd.); Gastroprotective flavone/flavone cpds. with therapeutic effect on inflammatory bowel disease. JP 1999514015; US 6025387; WO 9804541 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27802 1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-1-ethanone C16H16O4 详情 详情
(II) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(III) 27803 (E)-1-[4-(benzyloxy)-2-hydroxy-6-methoxyphenyl]-3-(3,4-dimethoxyphenyl)-2-propen-1-one C25H24O6 详情 详情
(IV) 27804 7-(benzyloxy)-2-(3,4-dimethoxyphenyl)-5-methoxy-4H-chromen-4-one C25H22O6 详情 详情
(V) 27805 2-(3,4-dimethoxyphenyl)-7-hydroxy-5-methoxy-4H-chromen-4-one C18H16O6 详情 详情
(VI) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(VII) 27806 tert-butyl 2-[[2-(3,4-dimethoxyphenyl)-5-methoxy-4-oxo-4H-chromen-7-yl]oxy]acetate C24H26O8 详情 详情

合成路线17

该中间体在本合成路线中的序号：(I)

The bromination of 3,4-dimethoxybenzaldehyde (I) with Br2 in acetic acid gives 2-bromo-4,5-dimethoxybenzaldehyde (II), which is selectively demethylated with H2SO4 yielding 2-bromo-5-hydroxy-4-methoxybenzaldehyde (III). The reductocondensation of (III) with 2-(4-hydroxyphenyl)ethylamine (IV) by means of NaBH4 affords the secondary amine (V), which is formylated with ethyl formate in dioxane/DMF giving the formamide (VI). The cyclization of (VI) by means of potassium hexacyanoferrate (III) and K2CO3 in hot toluene yields racemic N-formylbromonarwedine (+/-)(VII), which is reduced with lithium tri-tert-butoxyaluminum hydride furnishing a mixture of N-demethylbromogalanhamine (+/-)(VIII) and N-demethylepibromogalanthamine (+/-)(IX). After chromatographic separation of the two racemic epimers, resolution of racemic (+/-)(VIII) is carried out employing di-p-toluoyl tartaric acid to afford the required levo isomer. Alkylation of (-)(VIII) with 1-(3-chloropropyl)piperidine (X) gives (XI), which is finally converted to the title compound by reductive debromination in the presence of Zn and CaCl2.

参考文献 中间体
合成目标
【1】 Kuenburg, B.; et al.; Development of a pilot scale process for the anti-Alzheimer drug (-)-galanthamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion. Org Process Res Dev 1999, 3, 6, 425.
【2】 Kuenburg, B.; Frohlich, J.; Jordis, U.; Czollner, L. (Sanochemia Pharmazeutika AG); New benzazepine derivs., medicaments containing the same and their use to prepare medicaments. WO 9740049 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(II) 36481 2-bromo-4,5-dimethoxybenzaldehyde 5392-10-9 C9H9BrO3 详情 详情
(III) 36482 2-bromo-5-hydroxy-4-methoxybenzaldehyde 2973-59-3 C8H7BrO3 详情 详情
(IV) 19988 4-(2-Aminoethyl)phenol; Tyramine 51-67-2 C8H11NO 详情 详情
(V) 36483 4-bromo-5-[[(4-hydroxyphenethyl)amino]methyl]-2-methoxyphenol C16H18BrNO3 详情 详情
(VI) 36484 2-bromo-5-hydroxy-4-methoxybenzyl(4-hydroxyphenethyl)formamide C17H18BrNO4 详情 详情
(VII) 36485 1-bromo-3-methoxy-6-oxo-3a,5,6,9,10,12b-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-11(12H)-carbaldehyde C17H18BrNO4 详情 详情
(VIII) 36486 (4aS,6R,8aS)-1-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol C16H18BrNO3 详情 详情
(IX) 36487 (4aS,6S,8aS)-1-bromo-3-methoxy-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol C16H18BrNO3 详情 详情
(X) 36488 1-(3-chloropropyl)piperidine 5472-49-1 C8H16ClN 详情 详情
(XI) 36489 (4aS,6R,8aS)-1-bromo-3-methoxy-11-[3-(1-piperidinyl)propyl]-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-6-ol C24H33BrN2O3 详情 详情

合成路线18

该中间体在本合成路线中的序号：(II)

Condensation of 3,4-dimethoxybenzylamine (I) with 3,4-dimethoxybenzaldehyde (II) afforded imine (III), that was subsequently reduced to amine (IV) by means of NaBH4. Reaction of (V) with 2,4,6,8-tetrachloropyridopyrimidine (V) in THF at room temperature produced the 4,8-diamino derivative (VI). The remaining 2- and 6-chloro groups of (VI) were then displaced by aminoalcohol (VII) in boiling THF to furnish adduct (VIII). Finally, selective cleavage of two dimethoxybenzyl groups using trifluoroacetic acid gave rise to the title compound.

参考文献 中间体
合成目标
【1】 Barlow, H.C.; et al.; Resistance-modifying agents. Part 7: 2,6-Disubstituted-4,8-dibenzylaminopyrimido[5,4-d]pyrimidines that inhibit nucleoside transport in the presence of alpha1-acid glycoprotein (AGP). Bioorg Med Chem Lett 2000, 10, 6, 585.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 13920 (3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine 5763-61-1 C9H13NO2 详情 详情
(II) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(III) 41393 (3,4-dimethoxyphenyl)-N-[(E)-(3,4-dimethoxyphenyl)methylidene]methanamine; N-(3,4-dimethoxybenzyl)-N-[(E)-(3,4-dimethoxyphenyl)methylidene]amine C18H21NO4 详情 详情
(IV) 41394 N-(3,4-dimethoxybenzyl)(3,4-dimethoxyphenyl)methanamine; N,N-bis(3,4-dimethoxybenzyl)amine C18H23NO4 详情 详情
(V) 36173 2,4,6,8-tetrachloropyrimido[5,4-d]pyrimidine C6Cl4N4 详情 详情
(VI) 41395 N-[8-[bis(3,4-dimethoxybenzyl)amino]-2,6-dichloropyrimido[5,4-d]pyrimidin-4-yl]-N,N-bis(3,4-dimethoxybenzyl)amine; 2,6-dichloro-N(4),N(4),N(8),N(8)-tetrakis(3,4-dimethoxybenzyl)pyrimido[5,4-d]pyrimidine-4,8-diamine C42H44Cl2N6O8 详情 详情
(VII) 41397 1-amino-2-propanol 78-96-6 C3H9NO 详情 详情
(VIII) 41396 1-([4,8-bis[bis(3,4-dimethoxybenzyl)amino]-6-[(2-hydroxypropyl)amino]pyrimido[5,4-d]pyrimidin-2-yl]amino)-2-propanol C48H60N8O10 详情 详情

合成路线19

该中间体在本合成路线中的序号：(XXI)

Compound (XIII) can be obtained by reductocondensation of 3-chloro-4-fluoroaniline (XIX) with 3,4-dimethoxybenzaldehyde (XXI) using NaCNBH3 or NaBH(OAc)3 in AcOH/i-PrOH to yield the benzylaniline derivative (XXII), which by condensation with 4-chloro-7-fluoro-6-nitroquinazoline (XVIII) in i-PrOH gives the tertiary amine (XXIII) . Substitution of fluoroquinazoline (XXIII) with NaOMe in refluxing MeOH affords the 7-methoxyquinazoline derivative (XXIV), which is reduced to the quinazoline-4,6-diamine (XXV) by means of H2 over Raney Ni in THF. Finally, compound (XXV) is coupled with 4-(piperidin-1-yl)-2-butenoyl chloride (IV) in DMA .
4-(Piperidin-1-yl)-2-butenoyl chloride (IV) can be prepared by condensation of methyl 4-bromocrotonate (XI) with piperidine (X) to yield methyl 4-(piperidin-1-yl)-2-butenoate (XXVI), which is then hydrolyzed with HCl to give 4-(piperidin-1-yl)-2-butenoic acid (XXVII). Finally, acid (XXVII) is reacted with (COCl)2 in the presence of DMF in CH2Cl2 .

参考文献 中间体
合成目标
【1】 Fakhoury, S.A., Lee, H.T., Reed, J.E., Schlosser, K.M., Sexton, K.E., Tecle, H., Winters, R.T. (Pfizer, Inc.). 4-Phenylamino-quinazolin-6-yl-amides. EP 1746999, JP 200753668, JP 2009007363, US 2005250761, US 7772243, WO 2005107758.
【2】 Bridges, A.J., Horne, N.M., Jacks, T.E. et al. (Pfizer, Inc.). Preparation of substituted quinazolines. JP 2006517959, US 2004158065, WO 2004069791.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
（XXVI) 68482 (E)-methyl 4-(piperidin-1-yl)but-2-enoate 　 C10H17NO2 详情 详情
(IV) 68473 4-(piperidin-1-yl)-2-butenoyl chloride；(E)-4-(piperidin-1-yl)but-2-enoyl chloride 　 C9H14ClNO 详情 详情
(X) 10158 Piperidine 110-89-4 C5H11N 详情 详情
(XI) 26358 methyl (E)-4-bromo-2-butenoate 1117-71-1 C5H7BrO2 详情 详情
(XIII) 68477 (E)-N-(4-((3-chloro-4-fluorophenyl)(3,4-dimethoxybenzyl)amino)-7-methoxyquinazolin-6-yl)-4-(piperidin-1-yl)but-2-enamide 　 C33H35ClFN5O4 详情 详情
(XVIII) 19142 4-chloro-7-fluoro-6-nitroquinazoline C8H3ClFN3O2 详情 详情
(XIX) 18688 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline 367-21-5 C6H5ClFN 详情 详情
(XXI) 18304 3,4-Dimethoxybenzaldehyde; Veratraldehyde 120-14-9 C9H10O3 详情 详情
(XXII) 68478 3-chloro-N-(3,4-dimethoxybenzyl)-4-fluoroaniline 　 C15NClFO2 详情 详情
(XXIII) 68479 N-(3-chloro-4-fluorophenyl)-N-(3,4-dimethoxybenzyl)-6-fluoro-7-nitroquinazolin-4-amine 　 C23H17ClF2N4O4 详情 详情
(XXIV) 68480 N-(3-chloro-4-fluorophenyl)-N-(3,4-dimethoxybenzyl)-6-methoxy-7-nitroquinazolin-4-amine 　 C24H20ClFN4O5 详情 详情
(XXV) 68481 N4-(3-chloro-4-fluorophenyl)-N4-(3,4-dimethoxybenzyl)-6-methoxyquinazoline-4,7-diamine 　 C24H22ClFN4O3 详情 详情
(XXVII) 26709 (E)-4-(1-piperidinyl)-2-butenoic acid；(E)-4-(piperidin-1-yl)but-2-enoic acid C9H15NO2 详情 详情
Extended Information