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【结 构 式】 
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【分子编号】21347 【品名】(2S)pyrrolidinylmethanol 【CA登记号】23356-96-9 |
【 分 子 式 】C5H11NO 【 分 子 量 】101.14848 【元素组成】C 59.37% H 10.96% N 13.85% O 15.82% |
合成路线1
该中间体在本合成路线中的序号：(III)This compound is obtained by condensation of 2(S)-(aminomethyl)-1-ethylpyrrolidine (I) with 5-(aminosulfonyl)-2-methoxybenzoyl chloride (II) by means of K2CO3 in acetone. The starting compounds (I) and (II) are obtained as follows: a) The acylation of 2(S)-(hydroxymethyl)pyrrolidine (III) with acetic anhydride in refluxing methanol gives 1-acetyl-2(S)-(hydroxymethyl)pyrrolidine (IV), which by reaction with SOCl2 in CHCl3 is converted into 1-acetyl-2(S)-(chloromethyl)pyrrolidine (V). The reaction of (V) with sodium azide in hot DMF affords the corresponding azide (VI), which is reduced with LiAlH4 in refluxing THF to yield the desired product (I). b) The methylation of 2-hydroxybenzaldehyde (VII) with dimethyl sulfate and K2SO3 in refluxing acetone gives 2-methoxybenzaldehyde (VIII), which is oxidized with KMnO4 in hot aqueous NaOH affording 2-methoxybenzoic acid (IX). The sulfonation of (IX) with hot chlorosulfonic acid yields 5-(chlorosulfonyl)-2-methoxybenzoic acid (X), which is finally treated with 28% aqueous NaOH to give the desired product (II).
| 【1】 Al-Koutayni-Rifai, M.; Jamet, G.; Kerr, R.R.; Jung, L.; Koffel, J.C.; Synthesis of D3-sulpiride and its (R) and (S) isomers. J Label Compd Radiopharm 1989, 27, 7, 811. |
| 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) | 21345 | (2S)-1-Ethyl-2-(aminomethyl)pyrrolidine; [(2S)-1-Ethylpyrrolidinyl]methanamine | C7H16N2 | 详情 | 详情 | |
| (II) | 21346 | 5-(aminosulfonyl)-2-methoxybenzoyl chloride | C8H8ClNO4S | 详情 | 详情 | |
| (III) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (IV) | 21348 | 1-[(2S)-2-(hydroxymethyl)pyrrolidinyl]-1-ethanone | C7H13NO2 | 详情 | 详情 | |
| (V) | 21349 | 1-[(2S)-2-(chloromethyl)pyrrolidinyl]-1-ethanone | C7H12ClNO | 详情 | 详情 | |
| (VI) | 21350 | 1-[(2S)-2-(azidomethyl)pyrrolidinyl]-1-ethanone | C7H12N4O | 详情 | 详情 | |
| (VII) | 21351 | 2-Hydroxybenzaldehyde;Salicylic aldehyde；2-Formylphenol;salicylaldehyde | 90-02-8 | C7H6O2 | 详情 | 详情 |
| (VIII) | 12568 | 2-Methoxybenzaldehyde; o-Methoxybenzaldehyde | 135-02-4 | C8H8O2 | 详情 | 详情 |
| (IX) | 13926 | 2-Methoxybenzoic acid; o-Methoxybenzoic Acid | 579-75-9 | C8H8O3 | 详情 | 详情 |
| (X) | 21354 | 5-(chlorosulfonyl)-2-methoxybenzoic acid | C8H7ClO5S | 详情 | 详情 | |
| (XI) | 21355 | 5-(aminosulfonyl)-2-methoxybenzoic acid; 2-methoxy-5-sulfamoylbenzoic acid | 22117-85-7 | C8H9NO5S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VIII)The reaction of L-prolinol (VIII) with Boc2O gives N-Boc-L-prolinol (IX), which is oxidized with SO3/pyridine in DMSO to afford N-Boc-L-prolinal (X). The condensation of (X) with the propionate ester (XI), by means of LDA in THF, affords the 3-hydroxy-3-(2-pyrrolidinyl)propionate ester (XII), which is methylated with diazomethane and BF3 in dichloromethane to provide the corresponding methoxy derivative (XIII). The epimerization of the (S)-methyl group of group of (XIII) by means of t-Bu-OK in THF gives the corresponding (R)-methyl derivative (XIV), which is finally hydrogenolyzed with H2 over Pd/C in ethyl acetate/methanol to yield the desired pyrrolidinylpropionic acid intermediate (XV).
| 【1】 Pettit, G.R.; Singh, S.B.; Williams, M.D.; Herald, D.L.; Hogan, F.; Burkett, D.D.; Clewlow, P.J.; The absolute configuration and synthesis of natural (-)-Dolastatin 10. J Am Chem Soc 1989, 111, Suppl. 3, 5463. |
| 【2】 Pettit, G.R.; Srirangam, J.K.; Singh, S.B.; Williams, M.D.; Herald, D.L.; Barkóczy, J.; Kantoci, D.; Hogan, F.; Dolastatins 24. Synthesis of (-)-dolastatin 10. X-Ray molecular structure of N,N-dimethylvalyl-valyl-dolaisoleucine tert-butyl ester. J Chem Soc Perkins Trans I 1996, 8, Suppl. 3, 859-63. |
| 【3】 Pettit, G.R.; Singh, S.B. (Arizona State University); Synthesis of dolastatin 10. US 4978744 . |
| 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) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (IX) | 49819 | (S)-1-(tert-Butoxycarbonyl)-2-pyrrolidinenemethanol | C10H19NO3 | 详情 | 详情 | |
| (X) | 16724 | tert-Butyl (2S)-2-formyltetrahydro-1H-pyrrole-1-carboxylate; tert-Butoxycarbonyl-L-prolinal | 69610-41-9 | C10H17NO3 | 详情 | 详情 |
| (XI) | 54631 | (1S)-2-hydroxy-1,2,2-triphenylethyl propionate | C23H22O3 | 详情 | 详情 | |
| (XII) | 54632 | tert-butyl (2S)-2-((1R,2S)-1-hydroxy-3-{[(1S)-2-hydroxy-1,2,2-triphenylethyl]oxy}-2-methyl-3-oxopropyl)-1-pyrrolidinecarboxylate | C33H39NO6 | 详情 | 详情 | |
| (XIII) | 54633 | tert-butyl (2S)-2-((1R,2S)-3-{[(1S)-2-hydroxy-1,2,2-triphenylethyl]oxy}-1-methoxy-2-methyl-3-oxopropyl)-1-pyrrolidinecarboxylate | C34H41NO6 | 详情 | 详情 | |
| (XIV) | 54634 | tert-butyl (2S)-2-((1R,2R)-3-{[(1S)-2-hydroxy-1,2,2-triphenylethyl]oxy}-1-methoxy-2-methyl-3-oxopropyl)-1-pyrrolidinecarboxylate | C34H41NO6 | 详情 | 详情 | |
| (XV) | 23520 | (2R,3R)-3-[(2S)-1-(tert-butoxycarbonyl)pyrrolidinyl]-3-methoxy-2-methylpropionic acid | C14H25NO5 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(V)Reaction of vanillic acid (I) with 3-bromopropanol gave ether (II). Subsequent nitration of (II) with simultaneous oxidation of the primary alcohol employing nitric acid afforded the nitro diacid (IV), which by chemoselective esterification in the presence of a catalytic amount of p-toluenesulfonic acid yielded monoester (IV). After conversion of (IV) to the acid chloride upon treatment with oxalyl chloride, coupling with (S)-2-(hydroxymethyl)pyrrolidine (V) gave amide (VI). Catalytic hydrogenation of the nitro group of (VI), followed by protection of the intermediate aniline with 2,2,2-trichloroethyl chloroformate provided carbamate (VII). Further Swern oxidation of the alcohol group of (VII) with concomitant cyclization generated the pyrrolobenzodiazepine (VIII). The methyl ester of (VIII) was then hydrolyzed to carboxylic acid (IX).
| 【1】 Baraldi, P.G.; Cacciari, B.; Guiotto, A.; Leoni, A.; Romagnoli, R.; Spalluto, G.; Mongelli, N.; Howard, P.W.; Thurston, D.E.; Bianchi, N.; Gambari, R.; Design, synthesis and biological activity of a pyrrolo[2,1-c][1,4]benzodiazepine (PBD)-distamycin hybrid. Bioorg Med Chem Lett 1998, 8, 21, 3019. |
| 【2】 Cacciari, B.; Baraldi, P.G.; Balboni, G.; et al.; Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1,4]benzodiazepine and minor-groove-binding oligopyrrole carriers. J Med Chem 1999, 42, 25, 5131. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 12573 | 3-Bromo-1-propanol; 3-Bromopropanol | 627-18-9 | C3H7BrO | 详情 | 详情 | |
| (I) | 17786 | 4-hydroxy-3-methoxybenzoic acid; Vanillic acid | 121-34-6 | C8H8O4 | 详情 | 详情 |
| (II) | 26881 | 4-(3-hydroxypropoxy)-3-methoxybenzoic acid | C11H14O5 | 详情 | 详情 | |
| (III) | 26882 | 4-(2-carboxyethoxy)-5-methoxy-2-nitrobenzoic acid | C11H11NO8 | 详情 | 详情 | |
| (IV) | 26883 | 5-methoxy-4-(3-methoxy-3-oxopropoxy)-2-nitrobenzoic acid | C12H13NO8 | 详情 | 详情 | |
| (V) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (VI) | 26884 | methyl 3-(4-[[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl]-2-methoxy-5-nitrophenoxy)propanoate | C17H22N2O8 | 详情 | 详情 | |
| (VII) | 26885 | methyl 3-(4-[[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl]-2-methoxy-5-[[(2,2,2-trichloroethoxy)carbonyl]amino]phenoxy)propanoate | C20H25Cl3N2O8 | 详情 | 详情 | |
| (VIII) | 26886 | 2,2,2-trichloroethyl (11S,11aS)-11-hydroxy-7-methoxy-8-(3-methoxy-3-oxopropoxy)-5-oxo-2,3,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-10(5H)-carboxylate | C20H23Cl3N2O8 | 详情 | 详情 | |
| (IX) | 26887 | 3-([(11S,11aS)-11-hydroxy-7-methoxy-5-oxo-10-[(2,2,2-trichloroethoxy)carbonyl]-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-8-yl]oxy)propionic acid | C19H21Cl3N2O8 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(III)The known benzofuran carbinol (I) was converted to mesylate (II) upon treatment with methanesulfonyl chloride and triethylamine and then condensed with (S)-prolinol (III) at 120 C to afford adduct (IV). Subsequent chlorination of (IV) with concomitant rearrangement by means of thionyl chloride in benzene produced the 3-chloropiperidine derivative (V). The reaction of (V) with 4-hydroxybenzaldehyde (VI) in the presence of K2CO3 in DMF at 80 C furnished a mixture of six- and five-membered ring products (VII) and (VIII), which were separated by column chromatography. Condensation of the required aldehyde (VIII) with thiazolidinedione (IX) using piperidinium benzoate in refluxing toluene provided the target benzylidene thiazolidine, which was finally converted to the corresponding maleate salt.
| 【1】 Reddy, K.A.; Lohray, B.B.; Brushan, V.; et al.; Novel antidiabetic and hypolipidemic agents. 3. Benzofuran-containing thiazolidinediones. J Med Chem 1999, 42, 11, 1927. |
| 【2】 Ramanujam, R.; Chakrabarti, R.; Lohray, B.B.; Bajji, A.C.; Lohray, V.B.; Alla, S.R. (Dr. Reddy's Research Foundation); Heterocyclic cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5889032 . |
| 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) | 30773 | [5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methanol | C21H26O3 | 详情 | 详情 | |
| (II) | 30774 | [5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl methanesulfonate | C22H28O5S | 详情 | 详情 | |
| (III) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (IV) | 30775 | ((2S)-1-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]pyrrolidinyl)methanol | C26H35NO3 | 详情 | 详情 | |
| (V) | 30776 | (3R)-1-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]-3-chloropiperidine; benzyl 3-[[(3R)-3-chloropiperidinyl]methyl]-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl ether | C26H34ClNO2 | 详情 | 详情 | |
| (VI) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (VII) | 30777 | 4-[((3R)-1-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]piperidinyl)oxy]benzaldehyde | C33H39NO4 | 详情 | 详情 | |
| (VIII) | 30778 | 4-[((2S)-1-[[5-(benzyloxy)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-yl]methyl]pyrrolidinyl)methoxy]benzaldehyde | C33H39NO4 | 详情 | 详情 | |
| (IX) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(II)2-Chloropyridine (I) was condensed with (S)-prolinol (II) to furnish the pyridinylpyrrolidine (III). Subsequent alkylation of the hydroxyl group of (III) with 4-fluorobenzaldehyde (IV) using NaH in hot DMF gave ether (V). Knoevenagel condensation of (V) with 2,4-thiazolidinedione (VI) in the presence of benzoic acid and piperidine afforded the required benzylidene thiazolidine, which was finally treated with maleic acid in acetone to yield the title maleate salt.
| 【1】 Reddy, A.S.; Lohray, B.B.; Bhushan, V.; et al.; Novel euglycemic and hypolipidemic agents. 4. Pyridyl- and quinolinyl-containing thiazolidinediones. J Med Chem 1999, 42, 14, 2569. |
| 【2】 Ramanujam, R.; Lohray, B.B.; Alla, S.R.; Chakrabarti, R.; Paraselli, R.B.; Lohray, V.B. (Dr. Reddy's Research Foundation); Thiazolidinedione cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. thereof. WO 9741120 . |
| 【3】 Rao, P.B.; Ramanujam, R.; Alla, S.R.; Lohray, V.B.; Chakrabarti, R.; Lohray, B.B. (Dr. Reddy's Research Foundation); Heterocyclic cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5919782 . |
| 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) | 17503 | 2-chloropyridine | 109-09-1 | C5H4ClN | 详情 | 详情 |
| (II) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (III) | 34806 | [(2S)-1-(2-pyridinyl)pyrrolidinyl]methanol | C10H14N2O | 详情 | 详情 | |
| (IV) | 12337 | 4-fluorobenzaldehyde | 459-57-4 | C7H5FO | 详情 | 详情 |
| (V) | 34807 | 4-[[(2S)-1-(2-pyridinyl)pyrrolidinyl]methoxy]benzaldehyde | C17H18N2O2 | 详情 | 详情 | |
| (VI) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(II)Mesylate (I) is heated with L-prolinol (II) to furnish pyrrolidine derivative (III), which can be converted into (VII) by different ways: 1) Treatment of (III) with t-BuOK and reaction with 4-fluorobenzaldehyde (IV) in DMF. 2) Conversion of (III) into chloropiperidine derivative (V) by means of SOCl2 in benzene, followed by reaction with 4-hydroxyaldehyde (VI) and K2CO3 in DMF in and chromatographic separation. 3) Mitsunobu reaction between (III) and 4-hydroxyaldehyde (VI) by treatment with PPh3 and DEAD in THF, followed by chromatographic separation. Derivative (VII) is condensed with 2,4-thiazolidinedione (VIII) in toluene in the presence of piperidine and benzoic acid to afford (IX), which is finally converted into its maleate form by treatment with maleic acid in Et2O.
| 【1】 Lohray, B.B.; Anji Reddy, K.; Bhushan, V.; et al.; Novel antidiabetic and hypolipidemic agents. 5. Hydroxyl versus benzyloxy containing chroman derivatives. J Med Chem 1999, 42, 17, 3265. |
| 【2】 Alla, S.R.; Ramanujam, R.; Bajji, A.C.; Lohray, B.B.; Lohray, V.B.; Chakrabarti, R. (Dr. Reddy's Research Foundation; Reddy-Cheminor Inc.); Novel heterocyclic cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. WO 9741121 . |
| 【3】 Ramanujam, R.; Chakrabarti, R.; Lohray, B.B.; Bajji, A.C.; Lohray, V.B.; Alla, S.R. (Dr. Reddy's Research Foundation); Heterocyclic cpds. having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compsns. containing them. US 5889032 . |
| 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) | 26454 | 6-(benzyloxy)-2,5,7,8-tetramethyl-2-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)chromane | C24H32O3S | 详情 | 详情 | |
| (II) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (III) | 42275 | ((2S)-1-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]pyrrolidinyl)methanol | C26H35NO3 | 详情 | 详情 | |
| (IV) | 12337 | 4-fluorobenzaldehyde | 459-57-4 | C7H5FO | 详情 | 详情 |
| (V) | 42276 | (3R)-1-[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]-3-chloropiperidine; benzyl 2-[(3R)-3-chloropiperidinyl]-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl ether | C25H32ClNO2 | 详情 | 详情 | |
| (VI) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (VII) | 42277 | 4-[((2S)-1-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]pyrrolidinyl)methoxy]benzaldehyde | C33H39NO4 | 详情 | 详情 | |
| (VIII) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (IX) | 42278 | 5-((Z)-[4-[((2S)-1-[[6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-yl]methyl]pyrrolidinyl)methoxy]phenyl]methylidene)-1,3-thiazolidine-2,4-dione | C36H40N2O5S | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(IX)Treatment of salicyl alcohol (I) with benzyl bromide (II) in DMF in the presence of KOtBu affords benzyloxybenzyl alcohol (III), which is converted into its chloride form (IV) by means of SOCl2 in THF. Reaction of (IV) with PPh3 in refluxing toluene gives triphenyl phosphonium chloride derivative (V), which is then subjected to a Wittig reaction with aldehyde (VI) to yield olefine (VII). Catalytic hydrogenolysis of (VII) over Pd/C provides phenol derivative (VIII), which is then alkylated by reaction with tosylate (XVI) and KOtBu in dimethylacetamide to yield (XVII). Finally, ethoxycarbonyl derivative (XVII) is reduced by means of LiAlH4 in THF and converted into its hydrochloride form by treatment with HCl in dioxane. Intermediate (XVI) can be prepared as follows: Protection of 2(S)-pyrrolidinemethanol (IX) by reaction with ethyl chloroformate in the presence of Et3N in dichloromethane affords carbamate (XI), which is tosylated by means of Ts2O and Et3N in dichloromethane to yield (XII). One carbon elongation of (XII) by reaction with NaCN in DMF provides (XIII), which is then converted into ester (XIV) by means of H2SO4 in EtOH. Reduction of ester (XIV) with LiAlH4 in THF gives alcohol (XV), which is finally tosylated by reaction with Ts2O and Et3N in dichloromethane.
| 【1】 Fujimoto, K.; Tanaka, N.; Asai, F.; Ito, T.; Koike, H. (Sankyo Co., Ltd.); Phenoxyalkylamines, -pyrrolidines and -piperidines for the treatment and prevention of circulatory diseases and psychosis. EP 0600717; JP 1994234736; JP 1994306025; US 5556864 . |
| 【2】 Goto, R.; Hayakawa, M.; Ito, R.; Ogawa, T.; Sugidachi, A.; Tanaka, N.; Asai, F.; Fujimoto, K.; [2-(omega-Phenylalkyl)phenoxy]alkylamines II: Synthesis and selective serotonin-2 receptor binding. Chem Pharm Bull 2000, 48, 2, 245. |
| 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) | 42341 | 2-(hydroxymethyl)phenol | 90-01-7 | C7H8O2 | 详情 | 详情 |
| (II) | 12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 |
| (III) | 42342 | [2-(benzyloxy)phenyl]methanol | C14H14O2 | 详情 | 详情 | |
| (IV) | 42343 | benzyl 2-(chloromethyl)phenyl ether; 1-(benzyloxy)-2-(chloromethyl)benzene | C14H13ClO | 详情 | 详情 | |
| (V) | 42344 | [2-(benzyloxy)benzyl](triphenyl)phosphonium chloride | C32H28ClOP | 详情 | 详情 | |
| (VI) | 20589 | 3-methoxybenzaldehyde; m-Anisaldehyde | 591-31-1 | C8H8O2 | 详情 | 详情 |
| (VII) | 42345 | 1-(benzyloxy)-2-[(E)-2-(3-methoxyphenyl)ethenyl]benzene; benzyl 2-[(E)-2-(3-methoxyphenyl)ethenyl]phenyl ether | C22H20O2 | 详情 | 详情 | |
| (VIII) | 13604 | 2-(3-Methoxyphenethyl)phenol | C15H16O2 | 详情 | 详情 | |
| (IX) | 21347 | (2S)pyrrolidinylmethanol | 23356-96-9 | C5H11NO | 详情 | 详情 |
| (X) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
| (XI) | 42346 | ethyl (2S)-2-(hydroxymethyl)-1-pyrrolidinecarboxylate | C8H15NO3 | 详情 | 详情 | |
| (XII) | 42347 | ethyl (2S)-2-([[(4-methylphenyl)sulfonyl]oxy]methyl)-1-pyrrolidinecarboxylate | C15H21NO5S | 详情 | 详情 | |
| (XIII) | 42348 | ethyl (2S)-2-(cyanomethyl)-1-pyrrolidinecarboxylate | C9H14N2O2 | 详情 | 详情 | |
| (XIV) | 42349 | ethyl (2S)-2-(2-ethoxy-2-oxoethyl)-1-pyrrolidinecarboxylate | C11H19NO4 | 详情 | 详情 | |
| (XV) | 42350 | ethyl (2S)-2-(2-hydroxyethyl)-1-pyrrolidinecarboxylate | C9H17NO3 | 详情 | 详情 | |
| (XVI) | 42351 | ethyl (2S)-2-(2-[[(4-methylphenyl)sulfonyl]oxy]ethyl)-1-pyrrolidinecarboxylate | C16H23NO5S | 详情 | 详情 | |
| (XVII) | 42352 | ethyl (2S)-2-[2-[2-(3-methoxyphenethyl)phenoxy]ethyl]-1-pyrrolidinecarboxylate | C24H31NO4 | 详情 | 详情 |