合成路线1
该中间体在本合成路线中的序号:
(III) Free radical bromination of 3-tolunitrile gives 3-cyanobenzyl bromide, which is oxidized with hexamine/acetic acid to 3-cyanobenzaldehyde. A Knoevenagel reaction with malonic acid then gives 3-cyanocinnamic acid, which is reduced to the alcohol via the acid chloride. The tetrazole ring is formed by reaction of the alcohol with sodium azide and triethylamine hydrogen chloride in dimethyl acetamide. This tetrazole group is then protected using trityl chloride and triethylamine in dichloromethane. The key chiral epoxidation is conducted using tert-butyl hydroperoxide and catalytic quantities of diisopropyl L-tartrate and titanium (IV) isopropoxide. A Swern oxidation then gives the aldehyde, which is homolagated to the trans-alpha,beta-unsaturated aldehyde using the formyl methylene ylid.
This aldehyde is then reacted at -100 C with the ylid formed from n-decylphosphonium bromide and sodium bis(trimethylsilyl)amide in THF.
A base catalyzed Sn2 reaction between the diene epoxide and methyl 3-thiopropionate in methanol gives the protected analogue of LY-170680.
Finally, the protecting groups are removed using acid ion exchange resin followed by base hydrolysis in methanol/water. After chromatography LY-170680 is crystallized from acetone/hexane.
【1】
Wishart, G.; Baker, S.R.; Lucas, R.; Boot, J.R.; Sulukast. Drugs Fut 1991, 16, 5, 432.
|
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) |
13243 |
m-Tolunitrile; 3-Methylbenzonitrile
|
620-22-4 |
C8H7N |
详情 | 详情
|
(II) |
13244 |
alpha-Bromo-m-tolunitrile; 3-(Bromomethyl)benzonitrile
|
28188-41-2 |
C8H6BrN |
详情 | 详情
|
(III) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(IV) |
13246 |
(E)-3-(3-Cyanophenyl)-2-propenoic acid
|
|
C10H7NO2 |
详情 |
详情
|
(V) |
13247 |
(E)-3-(3-Cyanophenyl)-2-propenoyl chloride
|
|
C10H6ClNO |
详情 |
详情
|
(VI) |
13248 |
3-[(E)-3-Hydroxy-1-propenyl]benzonitrile
|
|
C10H9NO |
详情 |
详情
|
(VII) |
13249 |
(E)-3-[3-(1H-1,2,3,4-Tetraazol-5-yl)phenyl]-2-propen-1-ol
|
|
C10H10N4O |
详情 |
详情
|
(VIII) |
13250 |
(E)-3-[3-(2-trityl-2H-1,2,3,4-Tetraazol-5-yl)phenyl]-2-propen-1-ol
|
|
C29H24N4O |
详情 |
详情
|
(IX) |
13251 |
[(2S,3S)-3-[3-(2-trityl-2H-1,2,3,4-Tetraazol-5-yl)phenyl]oxiranyl]methanol
|
|
C29H24N4O2 |
详情 |
详情
|
(X) |
13252 |
(2R,3S)-3-[3-(2-trityl-2H-1,2,3,4-Tetraazol-5-yl)phenyl]-2-oxiranecarbaldehyde
|
|
C29H22N4O2 |
详情 |
详情
|
(XI) |
55468 |
2-(triphenylphosphoranylidene)acetaldehyde
|
|
C20H17OP |
详情 |
详情
|
(XII) |
13253 |
(E)-3-[(2S,3S)-3-[3-(2-trityl-2H-1,2,3,4-Tetraazol-5-yl)phenyl]oxiranyl]-2-propenal
|
|
C31H24N4O2 |
详情 |
详情
|
(XIII) |
13254 |
5-(3-[(2S,3S)-3-[(1E,3Z)-1,3-Tridecadienyl]oxiranyl]phenyl)-2-trityl-2H-1,2,3,4-tetraazole
|
|
C41H44N4O |
详情 |
详情
|
(XIV) |
13255 |
methyl 3-[((1R,2E,4Z)-1-[(S)-hydroxy[3-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)phenyl]methyl]-2,4-tetradecadienyl)sulfanyl]propanoate
|
|
C45H52N4O3S |
详情 |
详情
|
(XV) |
13256 |
methyl 3-[((1R,2E,4Z)-1-[(S)-hydroxy[3-(1H-1,2,3,4-tetraazol-5-yl)phenyl]methyl]-2,4-tetradecadienyl)sulfanyl]propanoate
|
|
C26H38N4O3S |
详情 |
详情
|
合成路线2
该中间体在本合成路线中的序号:
(V) The reaction of trifluoroacetoacetic acid ethyl ester (I) with (?)-isoborneol (II) at 130 C gives the corresponding isobornyl ester (III), which is condensed with cyclohexane-1,3-dione (IV) and 3-cyanobenzaldehyde (V) by means of ammonium acetate in refluxing ethanol to yield the octahydroquinolone (VI). The hydrolysis of the ester group of (VI), with simultaneous dehydration by means of TsOH in refluxing toluene affords 4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (VII) as a racemic mixture. Optical resolution of (VII) through the diastereomeric salt with 1(S)-phenylethylamine (VIII) in toluene/butanol provides the desired isomer (IX), which is finally decarboxylated in N-methyl-2-pyrrolidone at 210 C to furnish the target hexahydroquinolone.
【1】
Ashworth, I.; Hopes, P.; Levin, D.; Patel, I.; Salloo, R.; An asymmetric synthesis of a 4-substituted-1,4-dihydropyridine. Tetrahedron Lett 2002, 43, 28, 4931.
|
【2】
Warawa, J.E.; Ohnmacht, C.J. Jr.; Trainor, D.A.; Hulsizer, J.M. (AstraZeneca plc); Quinolone deriv. for treatment of urinary incontinence. EP 0755382; JP 1997512254; WO 9528388 .
|
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) |
62025 |
propyl 4,4,4-trifluoro-3-oxobutanoate
|
|
C7H9F3O3 |
详情 |
详情
|
(II) |
62026 |
(1R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
|
|
C10H18O |
详情 |
详情
|
(III) |
62027 |
(1R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl 4,4,4-trifluoro-3-oxobutanoate
|
|
C14H19F3O3 |
详情 |
详情
|
(IV) |
11244 |
1,3-Cyclohexanedione
|
504-02-9 |
C6H8O2 |
详情 | 详情
|
(V) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(VI) |
62028 |
(1R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-3-quinolinecarboxylate
|
|
C28H31F3N2O4 |
详情 |
详情
|
(VII) |
62029 |
4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid
|
|
C18H13F3N2O3 |
详情 |
详情
|
(VIII) |
10039 |
(1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine
|
3886-69-9 |
C8H11N |
详情 | 详情
|
(IX) |
62030 |
(4S)-4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid
|
|
C18H13F3N2O3 |
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-cyanobenzaldehyde (I) with trifluoroacetone (II) in piperidine gives 3-(4,4,4-trifluoro-3-oxo-2-butenyl)benzonitrile (III). The condensation of cyclohexane-1,3-dione (IV) with 1(R)-phenylethylamine (V) in refluxing toluene or THF yields the secondary enamine (VI), which is condensed with benzonitrile (III) by means of Tms-Cl in hot acetonitrile to afford the chiral adduct (VII). The cyclization of (VII) by means of NH3 in hot acetonitrile provides the chiral octahydroquinolone (VIII), which is finally dehydrated by means of TFA, MsOH, TsOH or HCl in refluxing acetonitrile to give the target hexahydroquinolone.
【1】
Patel, I.; Hopes, P. (AstraZeneca AB); Process for synthesis of alpha,beta-unsaturated ketones. WO 0210103 .
|
【2】
Patel, I.; Ashworth, I.; Levin, D. (AstraZeneca AB); Process for asymmetric synthesis of substd. 1,4-dihydropyridines. WO 0210134 .
|
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) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(II) |
35450 |
3,3-dibromo-1,1,1-trifluoroacetone
|
431-67-4 |
C3HBr2F3O |
详情 | 详情
|
(III) |
62031 |
3-[(E)-4,4,4-trifluoro-3-oxo-1-butenyl]benzonitrile
|
|
C11H6F3NO |
详情 |
详情
|
(IV) |
11244 |
1,3-Cyclohexanedione
|
504-02-9 |
C6H8O2 |
详情 | 详情
|
(V) |
10039 |
(1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine
|
3886-69-9 |
C8H11N |
详情 | 详情
|
(VI) |
62032 |
3-{[(1R)-1-phenylethyl]amino}-2-cyclohexen-1-one
|
|
C14H17NO |
详情 |
详情
|
(VII) |
62033 |
3-[(1S)-4,4-dimethyl-3-oxo-1-(6-oxo-2-{[(1R)-1-phenylethyl]amino}-1-cyclohexen-1-yl)pentyl]benzonitrile
|
|
C28H32N2O2 |
详情 |
详情
|
(VIII) |
62034 |
3-[(4S)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-4-quinolinyl]benzonitrile
|
|
C17H15F3N2O2 |
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 condensation of trifluoroacetoacetic acid ethyl ester (I) with cyclohexane-1,3-dione (II) and 3-cyanobenzaldehyde (III) by means of ammonium acetate in refluxing ethanol gives the octahydroquinolone (IV), which is hydrolyzed at its ester group by means of LiOH in hot ethanol/water to yield the corresponding carboxylic acid (V). Finally, this compound is dehydrated by means of TsOH in refluxing toluene to afford the target intermediate (rac)-4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (VI).
【1】
Ohnmacht, C.J.; Trainor, D.A.; Forst, J.M.; Stein, M.M.; Harris, R.J. (AstraZeneca plc); Quinolone and acridinone derivs. for the treatment of urinary incontinence. EP 0665834; JP 1996502282; US 5622964; WO 9408966 .
|
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) |
62025 |
propyl 4,4,4-trifluoro-3-oxobutanoate
|
|
C7H9F3O3 |
详情 |
详情
|
(II) |
11244 |
1,3-Cyclohexanedione
|
504-02-9 |
C6H8O2 |
详情 | 详情
|
(III) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(IV) |
62035 |
propyl 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-3-quinolinecarboxylate
|
|
C21H21F3N2O4 |
详情 |
详情
|
(V) |
62036 |
4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-3-quinolinecarboxylic acid
|
|
C18H15F3N2O4 |
详情 |
详情
|
(VI) |
62029 |
4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid
|
|
C18H13F3N2O3 |
详情 |
详情
|
合成路线5
该中间体在本合成路线中的序号:
(I) Strecker condensation of 3-cyanobenzaldehyde (I) with trimethylsilyl cyanide in the presence of (S)-2-phenylglycine (II) yielded the chiral aminonitrile (III) as the major diastereoisomer. Oxidative cleavage of the chiral auxiliary of (III) with lead tetraacetate, followed by acid hydrolysis of the nitrile groups provided the (S)-amino acid (IV), which was esterified with MeOH and Me3SiCl. The resulting aminoester (V) was coupled with carboxylic acid (VI) using diphenylphosphoryl azide to form amide ester (VII). Finally, saponification of both methyl esters of (VII) afforded the target dicarboxylate salt.
【1】
Baek, D.-J.; Park, Y.-K.; Heo, H.I.; Lee, M.; Yang, Z.; Choi, M.; Synthesis of 5-substituted quinazolinone derivatives and their inhibitory activity in vitro. Bioorg Med Chem Lett 1998, 8, 23, 3287.
|
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) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(II) |
10973 |
(2S)-2-Amino-2-phenyl-1-ethanol; (S)-2-Hydroxy-1-phenylethylamine; (S)-(+)-2-Phenylglycinol; (S)-2-Amino-2-phenyl-1-ethanol
|
20989-17-7 |
C8H11NO |
详情 | 详情
|
(III) |
29641 |
3-((S)-cyano[[(1R)-2-hydroxy-1-phenylethyl]amino]methyl)benzonitrile
|
|
C17H15N3O |
详情 |
详情
|
(IV) |
29642 |
3-[(S)-amino(carboxy)methyl]benzoic acid
|
|
C9H9NO4 |
详情 |
详情
|
(V) |
29643 |
methyl 3-[(1S)-1-amino-2-methoxy-2-oxoethyl]benzoate
|
|
C11H13NO4 |
详情 |
详情
|
(VI) |
29639 |
4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoic acid
|
|
C16H13N3O3S |
详情 |
详情
|
(VII) |
29644 |
methyl 3-[(1S)-1-([4-[(2-amino-6-methyl-4-oxo-3,4-dihydro-5-quinazolinyl)sulfanyl]benzoyl]amino)-2-methoxy-2-oxoethyl]benzoate
|
|
C27H24N4O6S |
详情 |
详情
|
合成路线6
该中间体在本合成路线中的序号:
(I) The reaction of 3-formylbenzonitrile (I) with methyl 2-bromoacetate (II) by means of activated Zn in hot THF gives 3-(3-cyanophenyl)-3-hydroxypropionic acid methyl ester (III), which is oxidized with activated MnO2 in hot dichloromethane yielding the oxoester (IV). The bromination of (IV) with NBS in CCl4 affords the alpha bromo derivative (V), which is cyclized with thioacetamide (VI) in hot THF affording 4-(3-cyanophenyl)-2-methylthiazole-5-carboxylic acid methyl ester (VII). The condensation of (VII) with 4'-amino-N-tert-butylbiphenyl-2-sulfonamide (VIII) by means of trimethylaluminum in toluene/dichloromethane gives the corresponding amide (IX), which is treated with hot TFA to eliminate the ter-butyl protecting group yielding intermediate (X). Finally, the cyano group of (X) is treated first with anhydrous HCl in methanol, and finally with ammonium carbonate in the same solvent to obtain the target amidine.
【1】
Quan, M.L.; Pinto, D.J.P.; Fevig, J.M.; Pruitt, J.R. (DuPont Pharmaceuticals Co.); Oxygen or sulfur containing heteroaromatics as fac. WO 9828282 .
|
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) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(II) |
12309 |
methyl 2-bromoacetate; methyl bromoacetate
|
96-32-2 |
C3H5BrO2 |
详情 | 详情
|
(III) |
28346 |
methyl 3-(3-cyanophenyl)-3-hydroxypropanoate
|
|
C11H11NO3 |
详情 |
详情
|
(IV) |
28347 |
methyl 3-(3-cyanophenyl)-3-oxopropanoate
|
|
C11H9NO3 |
详情 |
详情
|
(V) |
28348 |
methyl 2-bromo-3-(3-cyanophenyl)-3-oxopropanoate
|
|
C11H8BrNO3 |
详情 |
详情
|
(VI) |
19170 |
ethanethioamide
|
62-55-5 |
C2H5NS |
详情 | 详情
|
(VII) |
28349 |
methyl 4-(3-cyanophenyl)-2-methyl-1,3-thiazole-5-carboxylate
|
|
C13H10N2O2S |
详情 |
详情
|
(VIII) |
23363 |
4'-amino-N-(tert-butyl)[1,1'-biphenyl]-2-sulfonamide
|
|
C16H20N2O2S |
详情 |
详情
|
(IX) |
28350 |
N-[2'-[(tert-butylamino)sulfonyl][1,1'-biphenyl]-4-yl]-4-(3-cyanophenyl)-2-methyl-1,3-thiazole-5-carboxamide
|
|
C28H26N4O3S2 |
详情 |
详情
|
(X) |
28351 |
N-[2'-(aminosulfonyl)[1,1'-biphenyl]-4-yl]-4-(3-cyanophenyl)-2-methyl-1,3-thiazole-5-carboxamide
|
|
C24H18N4O3S2 |
详情 |
详情
|
合成路线7
该中间体在本合成路线中的序号:
(I) 3-Cyanobenzaldehyde (I) was converted to oxime (II) by reaction with hydroxylamine in pyridine. The intermediate nitrile oxide, generated from chlorination and further elimination of HCl, underwent a [2+3] cycloaddition with itaconic acid monomethyl ester (III) to produce the isoxazoline (IV). The carboxylate group of (IV) was then activated as the corresponding acid chloride (V) upon treatment with SOCl2. Boronic acid (VII) was prepared from N-tert-butyl benzenesulfonamide (VI) by lithiation with n-butyllithium, followed by reaction with triisopropyl borate and quenching with HCl. Subsequent Suzuki coupling of (VII) with 2-amino-5-bromopyrimidine (VIII) using Pd(PPh3)4 and Na2CO3 afforded the 2-amino-4-arylpyrimidine (IX). Condensation of amine (IX) with acid chloride (V) in the presence of Et3N gave amide (X). The N-tert-butyl group of (X) was then deprotected by means of trifluoroacetic acid to yield (XI) as the trifluoroacetate salt. The cyano group of (XI) was converted to imidate (XII) with HCl and MeOH. This was finally reacted with ammonium acetate in MeOH to furnish the title amidine.
【1】
Quan, M.L.; Liauw, A.Y.; Ellis, C.D.; et al.; Design and synthesis of isoxazoline derivatives as factor Xa inhibitors. 1. J Med Chem 1999, 42, 15, 2752.
|
【2】
Quan, M.L.; Wityak, J.; Galemmo, R.A. Jr.; Stouten, P.F.W.; Pruitt, J.R. (DuPont Pharmaceuticals Co.); Isoxazoline, isothiazoline and pyrazoline factor Xa inhibitors. EP 0874629; US 5939418; WO 9723212 .
|
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) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(II) |
23357 |
3-[(hydroxyimino)methyl]benzonitrile
|
|
C8H6N2O |
详情 |
详情
|
(III) |
34820 |
2-(2-methoxy-2-oxoethyl)acrylic acid
|
7338-27-4 |
C6H8O4 |
详情 | 详情
|
(IV) |
26630 |
3-(3-cyanophenyl)-5-(2-methoxy-2-oxoethyl)-4,5-dihydro-5-isoxazolecarboxylic acid
|
|
C14H12N2O5 |
详情 |
详情
|
(V) |
34821 |
methyl 2-[5-(chlorocarbonyl)-3-(3-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate
|
|
C14H11ClN2O4 |
详情 |
详情
|
(VI) |
26626 |
N-(tert-butyl)benzenesulfonamide
|
|
C10H15NO2S |
详情 |
详情
|
(VII) |
26627 |
2-[(tert-butylamino)sulfonyl]phenylboronic acid
|
|
C10H16BNO4S |
详情 |
详情
|
(VIII) |
34822 |
5-bromo-2-pyrimidinamine; 5-bromo-2-pyrimidinylamine
|
7752-82-1 |
C4H4BrN3 |
详情 | 详情
|
(IX) |
34823 |
2-(2-amino-5-pyrimidinyl)-N-(tert-butyl)benzenesulfonamide
|
|
C14H18N4O2S |
详情 |
详情
|
(X) |
34824 |
methyl 2-[5-[[(5-[2-[(tert-butylamino)sulfonyl]phenyl]-2-pyrimidinyl)amino]carbonyl]-3-(3-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate
|
|
C28H28N6O6S |
详情 |
详情
|
(XI) |
34825 |
methyl 2-[5-[([5-[2-(aminosulfonyl)phenyl]-2-pyrimidinyl]amino)carbonyl]-3-(3-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate
|
|
C24H20N6O6S |
详情 |
详情
|
(XII) |
34826 |
methyl 2-(5-[([5-[2-(aminosulfonyl)phenyl]-2-pyrimidinyl]amino)carbonyl]-3-[3-[imino(methoxy)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetate
|
|
C25H24N6O7S |
详情 |
详情
|
合成路线8
该中间体在本合成路线中的序号:
(IV) The title compound is prepared according to the Ugi reaction by combination of the four components: isocyanide (III), m-cyanobenzaldehyde (IV), 2-benzoylbenzoic acid (V), and histamine (VI) in refluxing MeOH
【1】
Hirth, B.H.; Bernasconi, R.; Biemann, H.P.; et al.; Discovery of TNF-alpha induced apoptosis inhibitors with activity in a murine model of multiple sclerosis: Glycine diamides. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 272.
|
【2】
Hirth, B.H.; Sneddon, S.F.; Kane, J.L.; Vinick, F.; Qiao, S.; Nahill, S.R. (Genzyme Corp.); Modulators of TNF-alpha signaling. WO 0187849 .
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中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(III) |
60310 |
|
|
C15H13N |
详情 |
详情
|
(IV) |
13245 |
3-Formylbenzonitrile; 3-Cyanobenzaldehyde
|
24964-64-5 |
C8H5NO |
详情 | 详情
|
(V) |
59365 |
2-benzophenone carboxylic acid; 2-Benzoylbenzoic acid; 2-Carboxybenzophenone; Benzophenone-2-carboxylic acid; O-benzoylbenzoic acid
|
85-52-9 |
C14H10O3 |
详情 | 详情
|
(VI) |
60311 |
2-(1H-imidazol-5-yl)-1-ethanamine; 2-(1H-imidazol-5-yl)ethylamine
|
|
C5H9N3 |
详情 |
详情
|