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【结 构 式】

【分子编号】50229

【品名】5-(4-[[tert-butyl(dimethyl)silyl]oxy]phenyl)-2,8-dimethoxy-11,12-dihydrobenzo[c]phenanthridin-6(5H)-one

【CA登记号】

【 分 子 式 】C31H35NO4Si

【 分 子 量 】513.70874

【元素组成】C 72.48% H 6.87% N 2.73% O 12.46% Si 5.47%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

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
Extended Information