3β-acetoxy-5β-12β,14β-dihydroxy-pregnan-20-one | 1325612-20-1

• 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-5β-12β,14β-dihydroxy-pregnan-20-one
• 英文别名: [(3S,5R,8R,9S,10S,12R,13S,14S,17S)-17-acetyl-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1325612-20-1
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: AKBKKLBFLKGMHG-CHCBUDSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3β-acetoxy-5β-cyclic 20-(ethyleneacetal)pregnan-12-one 在 水 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3β-acetoxy-5β-12β,14β-dihydroxy-pregnan-20-one
  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