12-O-β-tigloyl-3β-acetoxy-14β-hydroxy-pregn-5-ene-20-one | 1312364-43-4

• 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: 12-O-β-tigloyl-3β-acetoxy-14β-hydroxy-pregn-5-ene-20-one
• CAS: 1312364-43-4
• 化学式: C₂₈H₄₀O₆
• 分子量: 472.622
• InChiKey: BFKLKYFLHUJWIH-SWTLDOTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  89.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  12-O-β-tigloyl-3β-acetoxy-14β-hydroxy-pregn-5-ene-20-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以69%的产率得到12-O-β-tigloyl-3β,14β-dihydroxy-pregn-5-en-20-one
  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：

  (E)-2-甲基-2-丁烯酰氯 、 3β-acetoxy-12β,14β-dihydroxy-pregn-5-ene-20-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以80%的产率得到12-O-β-tigloyl-3β-acetoxy-14β-hydroxy-pregn-5-ene-20-one
  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