3β-acetoxy-16α-hydroxymethyl-5α-androstan-17β-ol | 359887-91-5

• 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-16α-hydroxymethyl-5α-androstan-17β-ol
• 英文别名: [(3S,5S,8R,9S,10S,13S,14S,16S,17S)-17-hydroxy-16-(hydroxymethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 359887-91-5
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: XUXFDTFRVSFCKT-MDKGJDARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-16α-hydroxymethyl-5α-androstan-17β-ol 在 吡啶 、 silver(I) acetate 作用下， 以 水 为溶剂， 反应 126.0h， 生成 16α-acetoxymethyl-5α-androstane-3β,17α-diacetate
  参考文献：
  名称：

  Neighboring group participation. Part 14. The preparation of the four stereoisomers of 16-hydroxymethyl-5α-androstane-3β,17-diol☆11☆ For a preceding paper in this series, see Ref. [1].

  摘要：

  16 alpha -Hydroxymethyl-5 alpha -androstane-3 beta ,17 beta and 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta were obtained from reduction of 16-acetoxymethylene-5-alpha -androstan-17-one. The corresponding 16 alpha ,17 alpha- and 16 beta ,17 alpha -hydroxymethyl isomers were obtained by neighboring group participation of the 16- and 17-acetates, respectively. The reactions involving carbocation formation also led to ring D rearrangement products. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00237-3
• 作为产物：
  描述：

  3β-acetoxy-16-acetoxymethylene-5α-androstan-17-one 在 钾硼氢 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 7.0h， 生成 3β-acetoxy-16α-hydroxymethyl-5α-androstan-17β-ol
  参考文献：
  名称：

  Neighboring group participation. Part 14. The preparation of the four stereoisomers of 16-hydroxymethyl-5α-androstane-3β,17-diol☆11☆ For a preceding paper in this series, see Ref. [1].

  摘要：

  16 alpha -Hydroxymethyl-5 alpha -androstane-3 beta ,17 beta and 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta were obtained from reduction of 16-acetoxymethylene-5-alpha -androstan-17-one. The corresponding 16 alpha ,17 alpha- and 16 beta ,17 alpha -hydroxymethyl isomers were obtained by neighboring group participation of the 16- and 17-acetates, respectively. The reactions involving carbocation formation also led to ring D rearrangement products. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00237-3