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【结 构 式】 
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【分子编号】11252 【品名】2-[(3-Oxo-1-cyclopenten-1-yl)amino]-1-cyclohexene-1-carbonitrile 【CA登记号】 |
【 分 子 式 】C12H14N2O 【 分 子 量 】202.25604 【元素组成】C 71.26% H 6.98% N 13.85% O 7.91% |
合成路线1
该中间体在本合成路线中的序号：(IX)The monohydroxylated metabolite of NIK-247, (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-1-ol (XII) has been synthesized as follows: The condensation of cyclopentane-1,3-dione (VIII) with 2-amino-1-cyclohexene-1-carbonitrile (VII) by means of PPE gives 2-(3-oxo-1-cyclopenten-1-yl)-1-cyclohexene-1-carbonitrile (IX), which is cyclized by means of BF3.Et2O to yield 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-1-one (X). The reduction of (X) with NaBH4 affords the corresponding racemic alcohol (XI), which is submitted to optical resolution with (+)-di-p-toluyltartaric acid to give the desired compound (XII).
| 【1】 Inada, H.; Yano, M.; Komatsu, T.; Iwamoto, M.; Suzuki, K.; Okada, K.; Synthesis of estimated metabolites of 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinoline monohydrochloride monohydrate (NIK-247). I.Synthesis of mono-hydroxylated metabolites. Yakugaku Zasshi 1995, 115, 12, 1016. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 11250 | 2-Amino-1-cyclohexene-1-carbonitrile | C7H10N2 | 详情 | 详情 | |
| (VIII) | 11251 | 1,3-Cyclopentanedione | 3859-41-4 | C5H6O2 | 详情 | 详情 |
| (IX) | 11252 | 2-[(3-Oxo-1-cyclopenten-1-yl)amino]-1-cyclohexene-1-carbonitrile | C12H14N2O | 详情 | 详情 | |
| (X) | 11253 | 9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-1-one | C12H14N2O | 详情 | 详情 | |
| (XI) | 11254 | 9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-1-ol | C12H16N2O | 详情 | 详情 | |
| (XII) | 63082 | (+)9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-1-ol | C12H16N2O | 详情 | 详情 |