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【结 构 式】 
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【分子编号】11242 【品名】2-Amino-1-cyclopentene-1-carbonitrile 【CA登记号】 |
【 分 子 式 】C6H8N2 【 分 子 量 】108.143 【元素组成】C 66.64% H 7.46% N 25.9% |
合成路线1
该中间体在本合成路线中的序号：(I)By reaction of 2-aminocyclopent-1-ene-1-carbonitrile (I) with cyclohexanone (II) in presence of polyphosphoric acid in benzene followed by treatment with hydrochloric acid in ethanol.
| 【1】 (Nauchno-Issledovatelsky Institut); 9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta(b)quinoline monohydrate hydrochloride as stimulant of neuro-muscular transmission of smooth muscles. US 4550113 . |
| 【2】 Lavretskaya, E.F.; Upadysheva, A.V.; Znamenskaya, A.P.; Sukhanova, S.A.; Grigorieva, N.D.; Penke, I.K.; Timofeeva, A.K. (Nauchno-Issledovatelsky Institut); Pharmaceutical preparation for learning stimulation and memory improvement. GB 2192129; US 4735953 . |
| 【3】 Graul, A.; Castaner, J.; Prous, J.; NIK-247. Drugs Fut 1994, 19, 4, 343. |
合成路线2
该中间体在本合成路线中的序号：(II)The monohydroxylated metabolite of NIK-247, (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol (VI) has been synthesized as follows: The condensation of cyclohexane-1,3-dione (I) with 2-amino-1-cyclopentene-1-carbonitrile (II) by means of PPE gives 2-(3-oxo-1-cyclohexen-1-yl)-1-cyclopentene-1-carbonitrile (III), which is cyclized by means of BF3.Et2O to yield 9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-one (IV). The reduction of (IV) with NaBH4 affords the corresponding racemic alcohol (V), which is submitted to optical resolution with (+)-di-p-toluyltartaric acid to give the desired compound (VI).
| 【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 |
|---|---|---|---|---|---|---|
| (I) | 11244 | 1,3-Cyclohexanedione | 504-02-9 | C6H8O2 | 详情 | 详情 |
| (II) | 11242 | 2-Amino-1-cyclopentene-1-carbonitrile | C6H8N2 | 详情 | 详情 | |
| (III) | 11246 | 2-[(3-Oxo-1-cyclohexen-1-yl)amino]-1-cyclopentene-1-carbonitrile | C12H14N2O | 详情 | 详情 | |
| (IV) | 11247 | 9-Amino-1,2,3,5,6,7-hexahydro-8H-cyclopenta[b]quinolin-8-one | C12H14N2O | 详情 | 详情 | |
| (V) | 11248 | 9-Amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol | C12H16N2O | 详情 | 详情 | |
| (VI) | 63081 | (+)-9-amino-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]quinolin-8-ol | C12H16N2O | 详情 | 详情 |