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【结 构 式】 
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【分子编号】57728 【品名】2-(4-chlorophenyl)acetaldehyde 【CA登记号】 |
【 分 子 式 】C8H7ClO 【 分 子 量 】154.59568 【元素组成】C 62.15% H 4.56% Cl 22.93% O 10.35% |
合成路线1
该中间体在本合成路线中的序号：(II)(4-Chlorophenyl)acetonitrile (I) is reduced with DIBAL to the aldehyde (II), which is subsequently converted to enamine (III) by treatment with dimethylamine in the presence of CaCl2 as the dehydrating agent. Condensation of enamine (III) with 2-cyclohexenone (IV) produces a mixture of the trans endo/exo substituted bicycloalkanones (V) and (VI), separable by column chromatography. Reduction of the endo isomer (V) with NaBH4 yields the bicyclic amino alcohol as a diastereomeric mixture. After chromatographic isolation, the desired isomer is esterified with benzoyl chloride to furnish the corresponding amino ester, which is finally converted to the title hydrochloride salt.
| 【1】 Coons, S.; et al.; Synthesis and pharmacology of potential site-specific cocaine abuse treatment agents: The role of the phenyl group in 2-substituted-6-aminobicyclo[2.2.2]octanes. Med Chem Res 2002, 11, 1, 24. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIIa) | 57732 | (1S,2R,4S,5R,6R)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-ol | C16H22ClNO | 详情 | 详情 | |
| (VIIb) | 57733 | (1S,2S,4S,5R,6R)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-ol | C16H22ClNO | 详情 | 详情 | |
| (I) | 22871 | 2-(4-chlorophenyl)acetonitrile | 140-53-4 | C8H6ClN | 详情 | 详情 |
| (II) | 57728 | 2-(4-chlorophenyl)acetaldehyde | C8H7ClO | 详情 | 详情 | |
| (III) | 57729 | (E)-2-(4-chlorophenyl)-N,N-dimethyl-1-ethenamine; N-[(E)-2-(4-chlorophenyl)ethenyl]-N,N-dimethylamine | C10H12ClN | 详情 | 详情 | |
| (IV) | 26253 | 2-cyclohexen-1-one；Cyclohex-2-enone；2-cyclohexenone | 930-68-7 | C6H8O | 详情 | 详情 |
| (V) | 57730 | (1S,4S,5R,6R)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-one | C16H20ClNO | 详情 | 详情 | |
| (VI) | 57731 | (1S,4S,5S,6S)-5-(4-chlorophenyl)-6-(dimethylamino)bicyclo[2.2.2]octan-2-one | C16H20ClNO | 详情 | 详情 |