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【结 构 式】 
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【分子编号】33946 【品名】(5S,8S,10S,13S,14S,16R,17S)-10,13,16,17-tetramethyl-17-propionyl-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one 【CA登记号】 |
【 分 子 式 】C24H36O2 【 分 子 量 】356.54864 【元素组成】C 80.85% H 10.18% O 8.97% |
合成路线1
该中间体在本合成路线中的序号：(VII)The methylation of 3beta-tetrahydropyranyloxy-16alpha,17alpha-dimethyl-DELTA9(11)-5alpha-pregnene-20-one (V) with lithium diisopropylamide and methyl iodide in THF gives 3beta-hydroxy-16alpha,17alpha,21-trimethyl-DELTA[9(11)]-5alpha-pregnene-20-one (VI), which is then oxidized with chromic acid in acetone yielding 16alpha,17alpha,21-trimethyl-DELTA[9(11)]-5alpha-pregnene-3,20-dione (VII). This compound is dehydrogenated as before affording 16alpha,17alpha,21-trimethyl-DELTA[1,4,9(11)]-pregnatriene-3,20-dione (VIII), which is finally hydroxylated by treatment first with NBS and then with butanethiol and chromous acetate in DMSO. The pregnene (VII) can also be obtained by methylation of 3-dimethyl-ketal-16alpha,17alpha-dimethyl-DELTA[9(11)]-5alpha-pregnene-3,20-dione (IX) with lithium diisopropylamide and methyl iodide in THF. The pregnatriene (VIII) can also be obtained by dehydrogenation of 16alpha,17alpha,21-trimethyl-DELTA[1,4,9(11)]-pregnatriene-3,20-dione (X), which is with Br2 in acetic acid and dehydrobromination with CaCO3 and LiBr in dimethylacetamide.
| 【1】 Woods, G.F.; et al.; Alkylated 3,20-diketo-steroids of the pregnane series. DE 2301317; FR 2168006; GB 1416427; JP 50004060; US 3862194 . |
| 【2】 Hillier, K.; Castaner, J.; Trimexolone. Drugs Fut 1977, 2, 10, 695. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 21890 | 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; 4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile | 84-58-2 | C8Cl2N2O2 | 详情 | 详情 |
| (V) | 33944 | 1-[(5S,8S,10S,13S,14S,16R,17S)-10,13,16,17-tetramethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-ethanone | C29H46O3 | 详情 | 详情 | |
| (VI) | 33945 | 1-[(5S,8S,10S,13S,14S,16R,17S)-3-hydroxy-10,13,16,17-tetramethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-propanone | C24H38O2 | 详情 | 详情 | |
| (VII) | 33946 | (5S,8S,10S,13S,14S,16R,17S)-10,13,16,17-tetramethyl-17-propionyl-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one | C24H36O2 | 详情 | 详情 | |
| (VIII) | 33948 | (8S,10R,13S,14S,16R,17S)-10,13,16,17-tetramethyl-17-propionyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one | C24H32O2 | 详情 | 详情 | |
| (IX) | 33947 | 1-[(5S,8S,10S,13S,14S,16S,17S)-3,3-dimethoxy-10,13,16,17-tetramethyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-1-propanone | C26H42O3 | 详情 | 详情 | |
| (X) | 33949 | (5S,8S,10S,13S,14S,16S,17S)-10,13,16,17-tetramethyl-17-propionyl-1,2,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one | C24H36O2 | 详情 | 详情 |