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【结 构 式】 
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【分子编号】50224 【品名】4-[[6-methoxy-3,4-dihydro-1(2H)-naphthalenylidene]amino]phenol 【CA登记号】 |
【 分 子 式 】C17H17NO2 【 分 子 量 】267.32752 【元素组成】C 76.38% H 6.41% N 5.24% O 11.97% |
合成路线1
该中间体在本合成路线中的序号：(III)Imine (III) was prepared by condensation of 6-methoxy-1-tetralone (I) with p-aminophenol (II) at 180 C. After silylation of the hydroxyl group of (III) with tert-butyldimethylsilyl chloride to give (IV), acylation of the enamine function with 2-bromo-5-methoxybenzoyl chloride (V) yielded enamide (VI). Halogenation of (VI) with N-bromosuccinimide gave the beta-bromo enamide (VII). Photocyclization of (VII) produced the benzophenanthridine (VIII), which was further dehydrogenated with DDQ providing (IX). Desilylation of (IX) to afford phenol (X) was achieved by treatment with hydrogen fluoride-pyridine.
| 【1】 Grese, T.A.; et al.; Photochemical synthesis of N-arylbenzophenanthridine selective estrogen receptor modulators (SERMs). J Med Chem 2001, 44, 17, 2857. |
| 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) | 17594 | 6-methoxy-3,4-dihydro-1(2H)-naphthalenone; 6-Methoxytetralone; 6-Methoxy-1-tetralone; 3,4-dihydro-6-methoxy-1(2H)-naphthalenone | 1078-19-9 | C11H12O2 | 详情 | 详情 |
| (II) | 15715 | 4-Aminophenol | 123-30-8 | C6H7NO | 详情 | 详情 |
| (III) | 50224 | 4-[[6-methoxy-3,4-dihydro-1(2H)-naphthalenylidene]amino]phenol | C17H17NO2 | 详情 | 详情 | |
| (IV) | 50225 | N-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-N-[6-methoxy-3,4-dihydro-1(2H)-naphthalenylidene]amine; 4-[[tert-butyl(dimethyl)silyl]oxy]-N-[6-methoxy-3,4-dihydro-1(2H)-naphthalenylidene]aniline | C23H31NO2Si | 详情 | 详情 | |
| (V) | 50226 | 2-Bromo-5-methoxybenzoyl chloride | 56658-04-9 | C8H6BrClO2 | 详情 | 详情 |
| (VI) | 50227 | 2-bromo-N-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-5-methoxy-N-(6-methoxy-3,4-dihydro-1-naphthalenyl)benzamide | C31H36BrNO4Si | 详情 | 详情 | |
| (VII) | 50228 | 2-bromo-N-(2-bromo-6-methoxy-3,4-dihydro-1-naphthalenyl)-N-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-5-methoxybenzamide | C31H35Br2NO4Si | 详情 | 详情 | |
| (VIII) | 50229 | 5-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-2,8-dimethoxy-11,12-dihydrobenzo[c]phenanthridin-6(5H)-one | C31H35NO4Si | 详情 | 详情 | |
| (IX) | 50230 | 5-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-2,8-dimethoxybenzo[c]phenanthridin-6(5H)-one | C31H33NO4Si | 详情 | 详情 | |
| (X) | 50231 | 5-(4-hydroxyphenyl)-2,8-dimethoxybenzo[c]phenanthridin-6(5H)-one | C25H19NO4 | 详情 | 详情 |