(3S,5S,8R,9S,10S,14S,16R)-16-Hydroxymethyl-10,17-dimethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | 359887-86-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5S,8R,9S,10S,14S,16R)-16-Hydroxymethyl-10,17-dimethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 英文别名: (3S,5S,8R,9S,10S,14S,16R)-16-(hydroxymethyl)-10,17-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 359887-86-8
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: WKROIZOFWSAVMZ-YAFLLMLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3S,5S,8R,9S,10S,14S,16R)-16-Hydroxymethyl-10,17-dimethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 在 吡啶 作用下， 生成 3β-acetoxy-16α-acetyloxymethyl-17-methyl-18-nor-5α-androst-13(17)-ene
  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-16α-acetoxymethyl-5α-androstan-17β-ol 在 吡啶 、 silver(I) acetate 作用下， 以 水 为溶剂， 反应 144.0h， 生成 (3S,5S,8R,9S,10S,14S,16R)-16-Hydroxymethyl-10,17-dimethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-3-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