3β-acetoxy-12-keto, cyclic 20-(ethylene acetal)pregn-5-ene | 1312364-39-8

• 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-12-keto, cyclic 20-(ethylene acetal)pregn-5-ene
• 英文别名: 3β-acetoxy-12-keto-cyclic 20-(ethylene acetal) pregn-5-ene；[(3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-12-oxo-1,2,3,4,7,8,9,11,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1312364-39-8
• 化学式: C₂₅H₃₆O₅
• 分子量: 416.558
• InChiKey: MVOPXGALCHSGRH-DJKVCXMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-12-keto, cyclic 20-(ethylene acetal)pregn-5-ene 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(2S,4aR,5S,6R)-4a-methyl-6-[(3S)-2-methyl-3-(2-methyl-1,3-dioxolan-2-yl)cyclopenten-1-yl]-5-(2-oxoethyl)-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl] acetate
  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：

  3,12α-diacetoxy-pregna-3,5-diene-20-one 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 3β-acetoxy-12-keto, cyclic 20-(ethylene acetal)pregn-5-ene
  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

文献信息

• Norrish–Prins reaction as a key step in the synthesis of 14β-hydroxy-5α (or 5β or Δ5,6)-pregnane derivatives
  作者：Philippe Geoffroy、Blandine Ressault、Eric Marchioni、Michel Miesch

  DOI：10.1016/j.steroids.2011.05.004

  日期：2011.9

  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.