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【结 构 式】 
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【分子编号】62035 【品名】propyl 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-3-quinolinecarboxylate 【CA登记号】 |
【 分 子 式 】C21H21F3N2O4 【 分 子 量 】422.4040296 【元素组成】C 59.71% H 5.01% F 13.49% N 6.63% O 15.15% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of trifluoroacetoacetic acid ethyl ester (I) with cyclohexane-1,3-dione (II) and 3-cyanobenzaldehyde (III) by means of ammonium acetate in refluxing ethanol gives the octahydroquinolone (IV), which is hydrolyzed at its ester group by means of LiOH in hot ethanol/water to yield the corresponding carboxylic acid (V). Finally, this compound is dehydrated by means of TsOH in refluxing toluene to afford the target intermediate (rac)-4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (VI).
| 【1】 Ohnmacht, C.J.; Trainor, D.A.; Forst, J.M.; Stein, M.M.; Harris, R.J. (AstraZeneca plc); Quinolone and acridinone derivs. for the treatment of urinary incontinence. EP 0665834; JP 1996502282; US 5622964; WO 9408966 . |
| 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) | 62025 | propyl 4,4,4-trifluoro-3-oxobutanoate | C7H9F3O3 | 详情 | 详情 | |
| (II) | 11244 | 1,3-Cyclohexanedione | 504-02-9 | C6H8O2 | 详情 | 详情 |
| (III) | 13245 | 3-Formylbenzonitrile; 3-Cyanobenzaldehyde | 24964-64-5 | C8H5NO | 详情 | 详情 |
| (IV) | 62035 | propyl 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-3-quinolinecarboxylate | C21H21F3N2O4 | 详情 | 详情 | |
| (V) | 62036 | 4-(3-cyanophenyl)-2-hydroxy-5-oxo-2-(trifluoromethyl)-1,2,3,4,5,6,7,8-octahydro-3-quinolinecarboxylic acid | C18H15F3N2O4 | 详情 | 详情 | |
| (VI) | 62029 | 4-(3-cyanophenyl)-5-oxo-2-(trifluoromethyl)-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid | C18H13F3N2O3 | 详情 | 详情 |