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【结 构 式】 
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【分子编号】62033 【品名】3-[(1S)-4,4-dimethyl-3-oxo-1-(6-oxo-2-{[(1R)-1-phenylethyl]amino}-1-cyclohexen-1-yl)pentyl]benzonitrile 【CA登记号】 |
【 分 子 式 】C28H32N2O2 【 分 子 量 】428.57436 【元素组成】C 78.47% H 7.53% N 6.54% O 7.47% |
合成路线1
该中间体在本合成路线中的序号：(VII)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 |