3β,12-β-bis(acetoxy), 5α-cyclic 20-(ethylene acetal)pregnane | 1325612-34-7

• 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,12-β-bis(acetoxy), 5α-cyclic 20-(ethylene acetal)pregnane
• CAS: 1325612-34-7
• 化学式: C₂₇H₄₂O₆
• 分子量: 462.627
• InChiKey: SEQPUHNLUNTUBW-YTXAUZKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β,12-β-bis(acetoxy), 5α-cyclic 20-(ethylene acetal)pregnane 在 甲醇 、 potassium hydroxide 作用下， 反应 16.0h， 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：

  3β,12β-Diacetoxy-5α-pregnanon-(20) 、 乙二醇 在 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到3β,12-β-bis(acetoxy), 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