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【结 构 式】 
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【分子编号】16393 【品名】(3S,4S)-3-(6-methoxy-3-pyridinyl)-4-[(trimethylsilyl)methyl]cyclohexanone 【CA登记号】 |
【 分 子 式 】C16H25NO2Si 【 分 子 量 】291.46554 【元素组成】C 65.93% H 8.65% N 4.81% O 10.98% Si 9.64% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：rac-(XXVI)7) Sestanj and his coworkers succeeded in synthesizing epibatidine by a conjugate addition intramolecular displacement strategy.Conjugate addition of higher order cyanocuprate (XXIV) to alpha,beta-unsaturated ketone (XXV) obtained the ketone (XXVI), which was converted to (XXVII) in 60% overall yield. Under Mitsunobu conditions with DEAD and PPh3 as reagents, only the beta-amino-tosylate cyclized to give the epibatidine ring system.
| 【1】 Sestanj, K.; Melenski, E.; Jirkovsky, I.; Synthesis of epibatidine. Tetrahedron Lett 1994, 35, 5417-20. |
| 【2】 Bai, D.; Xu, R.; Zhu, X.; Epibatidine. Drugs Fut 1997, 22, 11, 1210. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (rac-I) | 16385 | (+)-Epibatidine hydrochloride; (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane | 140111-52-0 | C11H13ClN2 | 详情 | 详情 |
| (rac-XVIII) | 16385 | (+)-Epibatidine hydrochloride; (1R,2R,4S)-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane | 140111-52-0 | C11H13ClN2 | 详情 | 详情 |
| rac-(XXVI) | 16393 | (3S,4S)-3-(6-methoxy-3-pyridinyl)-4-[(trimethylsilyl)methyl]cyclohexanone | C16H25NO2Si | 详情 | 详情 | |
| rac-(XXVII) | 16394 | N-[(3R,4S)-4-hydroxy-3-(6-methoxy-3-pyridinyl)cyclohexyl]-4-methylbenzenesulfonamide | C19H24N2O4S | 详情 | 详情 | |
| rac-(XXVIII) | 16395 | (1R,2R,4S)-2-(6-methoxy-3-pyridinyl)-7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]heptane; methyl 5-[(1R,2R,4S)-7-[(4-methylphenyl)sulfonyl]-7-azabicyclo[2.2.1]hept-2-yl]-2-pyridinyl ether | C19H22N2O3S | 详情 | 详情 | |
| (XXIV) | 16391 | (6-Methoxypyridin-3-yl)(2-thienyl)copper dilithium cyanide complex | C10H9CuNOS | 详情 | 详情 | |
| (XXV) | 16392 | 4-[(trimethylsilyl)methyl]-2-cyclohexen-1-one | C10H18OSi | 详情 | 详情 |
Extended Information