| 11β-羟基-16β-甲基-16α,17α-环丙烷基-孕甾-1,4-二烯-3,20-二酮的合成 |
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| 引用本文： | 杨冰,杨俊,翁玲玲,郑虎. 11β-羟基-16β-甲基-16α,17α-环丙烷基-孕甾-1,4-二烯-3,20-二酮的合成[J]. 有机化学, 2006, 26(6): 835-838 |
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| 作者姓名： | 杨冰 杨俊 翁玲玲 郑虎 |
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| 作者单位： | 四川大学华西药学院,成都,610041 |
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| 摘 要： | 由泼尼松龙(Prednisolone)为原料, 经甲磺酰化、甲基化、脱水、两次1,3-偶极反应以及其后的两次热分解共7步反应, 以23.5%的总收率首次制得了11β-羟基-16β-甲基-16α,17α-环丙烷基-孕甾-1,4-二烯-3,20-二酮这一重要的潜在药物及化学中间体. 实验同时发现, 1,3-偶极反应及其之后的热分解反应具有高度的立体选择性和区域选择性. 这种立体选择性和区域选择性通过1H NMR数据加以了证明.
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| 关 键 词： | 16α,17α-环丙烷基孕甾 1,3-偶极反应 热分解 立体选择性 区域选择性 药物中间体 合成 |
| 收稿时间： | 2005-06-01 |
| 修稿时间： | 2006-01-09 |
Synthesis of 11β-Hydroxy-16β-methyl-16α, 17α-methylene pregna-1,4-dien-3,20-dione |
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| YANG, Bing,YANG, Jun,WENG, Ling-Ling,ZHENG, Hu. Synthesis of 11β-Hydroxy-16β-methyl-16α, 17α-methylene pregna-1,4-dien-3,20-dione[J]. Chinese Journal of Organic Chemistry, 2006, 26(6): 835-838 |
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| Authors: | YANG Bing YANG Jun WENG Ling-Ling ZHENG Hu |
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| Affiliation: | West China School of Pharmacy, Sichuan University, Chengdu 610041 |
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| Abstract: | 11β-Hydroxy-16β-methyl-16α,17α-methylene-pregna-1,4-dien-3,20-dione, an im-portant chemical intermediate and excellent medicinal candidate, was prepared from prednisolone through 7 steps of methylsulfonylation, methylation, dehydration and double 1,3-dipolar reaction followed by double thermal decomposition with the total yield of 23.5%. The results showed that 1,3-dipolar reaction and ther-mal decomposition were highly regio- and stereo-selectivities proved by the data of 1H NMR. |
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| Keywords: | 16α,17α-methylenepregnanes 1,3-dipolar reaction thermal decomposition regioselectivity stereoselectivity medicinal intermediate synthesis |
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