3β-acetoxy-pregna-5,16-dien-20α_F-ol | 62014-21-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-acetoxy-pregna-5,16-dien-20α_F-ol
• 英文别名: [(3S,8R,9S,10R,13S,14S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 62014-21-5
• 化学式: C₂₃H₃₄O₃
• 分子量: 358.521
• InChiKey: QDRKGTJYDRBIBU-CTFSOQFLSA-N

物化性质

• 熔点：
  98-99 °C
• 沸点：
  464.0±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-pregna-5,16-dien-20α_F-ol 在 咪唑 、 氢氧化钾 、 aluminum isopropoxide 作用下， 以 甲醇 、 环己酮 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 (8R,9S,10R,13S,14S)-17-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthesis and in vitro activity of some epimeric 20α-hydroxy, 20-oxime and aziridine pregnene derivatives as inhibitors of human 17α-hydroxylase/c 17,20 -lyase and 5α-reductase

  摘要：

  Some epimeric 20-hydroxy, 20-oxime, 16 alpha, 17 alpha-, 17,20- and 20,21-aziridine derivatives of progesterone were synthesized and evaluated as inhibitors of human 17 alpha-hydroxylase/C-17,C-20-lyase (P450(17 alpha)) and 5 alpha-reductase (5 alpha-R). The reduction of 16-dehydropregenolone acetate (3a) was reinvestigated. NaBH4 in the presence of CeCl3 gave better stereoselectivity for 20 beta-ol [20 alpha/20 beta-OH (4 alpha/4 beta)=1/2.7] than LTBAH or the Meerwein-Pondroff method reported; reduction with Zn in HOAc formed exclusively 20 alpha-ol (4 alpha b). The 20 alpha- and 20 beta-hydroxy-4,16-pregnadien-3-one (9 alpha) and (9 beta) were synthesized from the alcohols 4 alpha b and 4 beta b. Several 20-oxime pregnadienes and 16 alpha,17 alpha-, 17,20- and 20,21-aziridinyl-5-pregnene derivatives were also synthesized. LiAlH4 reduction of the 16-en-20-oxime (12b) yielded 20 (R)-(13a) and 20(S)-17 alpha,20-aziridine (13b) and 20(R)-17 beta,20-aziridine (14a). Several compounds inhibited the human P450(17 alpha) with greater potency than ketoconzole. The 5 alpha-R enzyme assay showed that while (9 alpha) did not have any activity, (9 beta) and (3b) were potent 5 alpha-reductase (IC50 = 21 and 31 nM) inhibitors with activities similar to finasteride. The 20-oximes (17a) and (17b) were potent dual inhibitors for both 5 alpha-R (IC50 = 63 and 115 nM, compared to 33 nM for finasteride) and P450(17 alpha) (IC50 = 43 and 25 nM, compared to 78 nM for ketoconazole). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00110-2
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 溶剂黄146 、 锌 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3β-acetoxy-pregna-5,16-dien-20α_F-ol
  参考文献：
  名称：

  超声辅助合成中的锌反应1.有效还原烯酮

  摘要：

  在声化学条件下已经有效地完成了乙酸中α，β-不饱和酮的锌还原反应。不同的α-烯酮体系产生两种产物：烯烃和烯丙醇。报告了区域和立体选择性。

  DOI：

  10.1016/s0040-4039(00)60587-7

文献信息

• Ercoli; de Ruggieri, Il Farmaco, scienza e tecnica, 1952, vol. 7, p. 287,290
  作者：Ercoli、de Ruggieri

  DOI：——

  日期：——
• Kohout, Ladislav; Sanda, Vlastimil; Fajkos, Jan, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 5, p. 1503 - 1513
  作者：Kohout, Ladislav、Sanda, Vlastimil、Fajkos, Jan

  DOI：——

  日期：——
• US4102884A
  申请人：——

  公开号：US4102884A

  公开（公告）日：1978-07-25
• US4138553A
  申请人：——

  公开号：US4138553A

  公开（公告）日：1979-02-06