12α-acetoxy-5Hβ-pregnan-3,20-dione | 1102-97-2

• 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: 12α-acetoxy-5Hβ-pregnan-3,20-dione
• 英文别名: 12α-acetoxy-5β-pregnane-3,20-dione；12α-Acetoxy-5β-pregnan-3,20-dion；12α-Acetoxy-5β-pregnandion-(3,20)；[(5R,8R,9S,10S,12S,13S,14S,17S)-17-acetyl-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-12-yl] acetate
• CAS: 1102-97-2
• 化学式: C₂₃H₃₄O₄
• 分子量: 374.521
• InChiKey: WDXFAOOXKQDOOG-ZITVTUJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12α-acetoxy-5Hβ-pregnan-3,20-dione 在 溴 、 溶剂黄146 作用下， 反应 1.25h， 生成 4β-bromo-12α-acetoxy-5Hβ-pregnan-3,20-dione
  参考文献：
  名称：

  Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii

  摘要：

  14 beta-hydroxy pregnane glycosides extracted from Hoodia gordonii, a succulent plant isolated from Apocynaceae are suggested to have appetite suppressant properties in animals and humans. However, limited reports on biological studies concerning the appetite suppressant properties are available in the open literature. One reason for that is the poor availability of these glycosteroids because H. gordonii is a protected plant and the yield of extraction lies between 0.003% and 0.02%. Starting from 3 alpha,12 alpha-diacetoxy-pregnanone 1, we disclose in this report the synthesis of Hoodigogenin A. the aglycone of the natural 14 beta-hydroxy pregnane glycosides extracted from H. Gordonii. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.014
• 作为产物：
  描述：

  3α,12α-dihydroxy-5β-pregnan-20-one 在 吡啶 、 chromium(VI) oxide 、 甲醇 、 potassium carbonate 、 溶剂黄146 作用下， 生成 12α-acetoxy-5Hβ-pregnan-3,20-dione
  参考文献：
  名称：

  Cyclopentane-polyhydrophenanthrene derivatives

  摘要：

  公开号：

  US02142170A1

文献信息

• Über Steroide. (39. Mitteilung). Ein einfacher Abbau der Gallensäuren-Seitenkette zur Methylketonstufe
  作者：Ch. Meystre、H. Frey、A. Wettstein、K. Miescher

  DOI：10.1002/hlca.194402701230

  日期：——
• 12-Oxy- und 12-Keto-pregnan-Derivate
  作者：T. Reichstein、E. v. Arx

  DOI：10.1002/hlca.19400230194

  日期：——
• Über Bestandteile der Nebennierenrinde und verwandte Stoffe. 44. Mitteilung. 11-Dehydro-progesteron
  作者：C. W. Shoppee、T. Reichstein

  DOI：10.1002/hlca.19410240151

  日期：——
• Synthesis of Hoodigogenin A, aglycone of natural appetite suppressant glycosteroids extracted from Hoodia gordonii
  作者：Philippe Geoffroy、Blandine Ressault、Eric Marchioni、Michel Miesch

  DOI：10.1016/j.steroids.2011.03.014

  日期：2011.6

  14 beta-hydroxy pregnane glycosides extracted from Hoodia gordonii, a succulent plant isolated from Apocynaceae are suggested to have appetite suppressant properties in animals and humans. However, limited reports on biological studies concerning the appetite suppressant properties are available in the open literature. One reason for that is the poor availability of these glycosteroids because H. gordonii is a protected plant and the yield of extraction lies between 0.003% and 0.02%. Starting from 3 alpha,12 alpha-diacetoxy-pregnanone 1, we disclose in this report the synthesis of Hoodigogenin A. the aglycone of the natural 14 beta-hydroxy pregnane glycosides extracted from H. Gordonii. (C) 2011 Elsevier Inc. All rights reserved.
• Cyclopentane-polyhydrophenanthrene derivatives
  申请人：WINTHROP CHEM CO INC

  公开号：US02142170A1

  公开（公告）日：1939-01-03