3β,12β-Diacetoxy-5α-pregnanon-(20) | 5781-81-7

• 英文名称: 3β,12β-Diacetoxy-5α-pregnanon-(20)
• 英文别名: [(3S,5S,8R,9S,10S,12R,13S,14S,17S)-17-acetyl-12-acetyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 5781-81-7
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: VYZPGMGWYUEREY-ARDCGLKKSA-N

物化性质

• 沸点：
  490.5±40.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β,12β-Diacetoxy-5α-pregnanon-(20) 在 甲醇 、 对甲苯磺酸 、 原甲酸三乙酯 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 3α,12β-dihydroxy,5α-cyclic 20-(ethylene acetal)pregnane
  参考文献：
  名称：

  Norrish–Prins reaction as a key step in the synthesis of 14β-hydroxy-5α (or 5β or Δ5,6)-pregnane derivatives

  摘要：

  Numerous bioactive glycosteroids are characterized by aglycones bearing a 14 beta-hydroxy pregnane skeleton like boucerin and isoramanone. In general, the syntheses of the latter are achieved by acidic hydrolysis of the corresponding glycosteroids. These aglycones were also obtained by a combined Norrish type I-Prins reaction starting from the corresponding 12-keto-pregnane derivatives. However, for the Norrish-Prins reaction, no reports describe the influence of the A/B ring junction (cis or trans or Delta(5,6) double bond) or the influence of the substitution pattern at position 20. Herein, we describe the use of Norrish type I-Prins reactions to synthesize isoramanone and boucerin derivatives and their A/B cis and trans analogs. The influence of the parameters mentioned above is also presented. These studies showed that the A/B ring junction has little influence on the Norrish type I-Prins reaction but that the substitution pattern at position 20 is important. The presence of a dioxolane group induced not only the formation of the desired 14 beta-hydroxy pregnane derivatives in the highest yields but also the formation of new spiro derivatives. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.004
• 作为产物：
  描述：

  (25R)-5α-spirostan-3β,12β-diol diacetate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3β,12β-Diacetoxy-5α-pregnanon-(20)
  参考文献：
  名称：

  Tschesche,R. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 648, p. 185 - 195

  摘要：

  DOI：

文献信息

• Über Digitanolglykoside, 15. Synthese von 12α.20 <i>R</i> ‐Epoxy‐5α.14β.17βH‐pregnanen
  作者：Rudolf Tschesche、Ernst Schwinum

  DOI：10.1002/cber.19671000213

  日期：1967.2

  Ausgehend von Hecogeninacetat wurden auf zwei verschiedenen Wegen erstmals synthetisch 5α.14β.17βH-Pregnane (9, 19) mit einem 12α.20R-Oxidring hergestellt, wie er im Diginigenin, dort allerdings in der 20S-Konfiguration, vorkommen soll.

  Ausgehend冯Hecogeninacetat wurden奥夫ZWEI verschiedenen万德维根erstmals synthetisch5α.14β.17βH孕（9,19）MIT einem12α.20 ř -Oxidring hergestellt，魏某呃IM Diginigenin，在DER 20 Dort的allerdings小号-Konfiguration，vorkommen SOLL。
• 927. By-ways of synthesis of cortisone from hecogenin. Part II. A route to 11-oxygenated compounds through 3β : 20β-diacetoxy-11-bromoallopregnan-12-one
  作者：R. K. Callow、V. H. T. James

  DOI：10.1039/jr9560004744

  日期：——