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【结 构 式】 
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【分子编号】30505 【品名】5alpha,10alpha-Epoxy-3,3-(ethylenedioxy)-17alpha-(1-propynyl)estra-9(11)-en-17-beta-ol 【CA登记号】 |
【 分 子 式 】C23H30O4 【 分 子 量 】370.4888 【元素组成】C 74.56% H 8.16% O 17.27% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 3,3-(ethylenedioxy)estra-5(10),9(11)-diene-17(beta)-one (I) with propynylmagnesium bromine (II) in THF gives 3,3-(ethylenedioxy)-17(beta)-(propyn-1-yl)estra-5(10),9(11)-diene-17(beta)-ol (III), which is epoxidized with H2O2 in hexafluoroacetone-methylene chloride yielding 3,3-(ethylenedioxy)-17(beta)-(propyn-1-yl)-5(alpha),10(alpha)-epoxyestra-9(11)-en-17(beta)-ol (IV). The reaction of (IV) with 4-dimethylaminophenylmagnesium bromide (V) in THF affords 11(beta)-(4-dimethylaminophenyl)-3,3-(ethylenedioxy)-17(beta)-(propyn-1-yl)estra-9-en-17(beta)-ol (VI), which is finally deprotected by a treatment with HCl in metnanol.
| 【1】 Teutsch, J.G.; Costerousse, G.; Philibert, D.; Deraedt, R. (Aventis Pharma SA); Steroid. derivs. 11beta-substd.. FR 2497807; JP 1989279897; US 4447424; US 4978657; US 5043332 . |
| 【2】 Kottegoda, S.R.; Castaner, J.; Serradell, M.N.; Adaikan, P.G.; RU-486. Drugs Fut 1984, 9, 10, 755. |
| 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) | 30502 | 3,3-Ethylenedioxyestra-5(10),9(11)-dien-17-one | 5571-36-8 | C20H26O3 | 详情 | 详情 |
| (II) | 30503 | bromo(1-propynyl)magnesium | C3H3BrMg | 详情 | 详情 | |
| (III) | 30504 | 3,3-(Ethylenedioxy)-17alpha-(1-propynyl)estra-5(10),9(11)-dien-17-beta-ol | C23H30O3 | 详情 | 详情 | |
| (IV) | 30505 | 5alpha,10alpha-Epoxy-3,3-(ethylenedioxy)-17alpha-(1-propynyl)estra-9(11)-en-17-beta-ol | C23H30O4 | 详情 | 详情 | |
| (V) | 10863 | Bromo[4-(dimethylamino)phenyl]magnesium | 7353-91-5 | C8H10BrMgN | 详情 | 详情 |
| (VI) | 30506 | 11beta-[4-(Dimethylamino)phenyl]-3,3-(ethylenedioxy)-17alpha-(1-propynyl)estra-4,9-diien-17-beta-ol | C31H39NO3 | 详情 | 详情 |