16alpha-Methyl-5alpha-androstane-3beta,17alpha-diol | 385372-13-4

• 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: 16alpha-Methyl-5alpha-androstane-3beta,17alpha-diol
• 英文别名: (3S,5S,8R,9S,10S,13S,14S,16R,17R)-10,13,16-trimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 385372-13-4
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: NDONNZPZIROZJY-IZIVOVIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  16alpha-Methyl-5alpha-androstane-3beta,17alpha-diol 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 硫酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 72.0h， 生成 16alpha-Methyl-17alpha-hydroxy-5alpha-androstane-3-one
  参考文献：
  名称：

  Configurational analysis and relative binding affinities of 16-methyl-5α-androstane derivatives

  摘要：

  The four possible isomers 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta -dioI 1, 16 alpha -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta -diol 2, 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 alpha -diol 3 and 16 alpha -hydroxymethyl-5 alpha -androstane-3 beta ,17 alpha -diol 4 with proven configuration were converted into the corresponding 16 beta -methyl-5 alpha -androstane-3 beta ,17 beta -dioI 5, 16 alpha -methyl-5 alpha -androstane-3 beta ,17 beta -diol 6, 16 beta -methyl-5 alpha -androstane-3 beta ,17 alpha -diol 7, 16 alpha -methyl-5 alpha -androstane-3 beta ,17 alpha -diol 8, furthermore into the 16 beta -methyl-17 beta -hydroxy-5 alpha -androstane-3-one 13, 16 alpha -methyl-17 beta -hydroxy-5 alpha -androstan-3-one 14, 16 beta -methyl-17 alpha -hydroxy-5 alpha -androstan-3-one 15 and 16 alpha -methyl-17 alpha -hydroxy-5 alpha -androstan-3-one 16. The steric structures of the resulting epimers were determined by means of H-1-, and C-13-NMR spectroscopy. In this way, comparison was possible with the C-16 epimers 5, 6 and 13, 14 prepared earlier by a different route, and the series of isomers could be completed with the steric structures of 16 beta -methyl-17 alpha -hydroxy-5 alpha -androstan-3 beta -ol 7 and 16 alpha -methyl-17 alpha -hydroxy-5 alpha 8 and with their 3-keto derivatives 15 and 16. The relative binding affinities of the 16-methyl-5 alpha -androstane-3 beta ,17-diols 5, 6, 7, 8 and 17-hydroxy-16-methyl-5 alpha -androstan-3-ones 13, 14, 15, 16 were studied. The introduction of a 16-methyl substituent into 5 alpha -androstane molecules substantially decreases the binding affinity to the androgen receptor and 16 alpha -methyl derivatives were always bound more weakly than the 16 beta -methyl isomers. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00113-1
• 作为产物：
  描述：

  16α-acetoxymethyl-5α-androstane-3β,17α-diacetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 30.17h， 生成 16alpha-Methyl-5alpha-androstane-3beta,17alpha-diol
  参考文献：
  名称：

  Configurational analysis and relative binding affinities of 16-methyl-5α-androstane derivatives

  摘要：

  The four possible isomers 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta -dioI 1, 16 alpha -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta -diol 2, 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 alpha -diol 3 and 16 alpha -hydroxymethyl-5 alpha -androstane-3 beta ,17 alpha -diol 4 with proven configuration were converted into the corresponding 16 beta -methyl-5 alpha -androstane-3 beta ,17 beta -dioI 5, 16 alpha -methyl-5 alpha -androstane-3 beta ,17 beta -diol 6, 16 beta -methyl-5 alpha -androstane-3 beta ,17 alpha -diol 7, 16 alpha -methyl-5 alpha -androstane-3 beta ,17 alpha -diol 8, furthermore into the 16 beta -methyl-17 beta -hydroxy-5 alpha -androstane-3-one 13, 16 alpha -methyl-17 beta -hydroxy-5 alpha -androstan-3-one 14, 16 beta -methyl-17 alpha -hydroxy-5 alpha -androstan-3-one 15 and 16 alpha -methyl-17 alpha -hydroxy-5 alpha -androstan-3-one 16. The steric structures of the resulting epimers were determined by means of H-1-, and C-13-NMR spectroscopy. In this way, comparison was possible with the C-16 epimers 5, 6 and 13, 14 prepared earlier by a different route, and the series of isomers could be completed with the steric structures of 16 beta -methyl-17 alpha -hydroxy-5 alpha -androstan-3 beta -ol 7 and 16 alpha -methyl-17 alpha -hydroxy-5 alpha 8 and with their 3-keto derivatives 15 and 16. The relative binding affinities of the 16-methyl-5 alpha -androstane-3 beta ,17-diols 5, 6, 7, 8 and 17-hydroxy-16-methyl-5 alpha -androstan-3-ones 13, 14, 15, 16 were studied. The introduction of a 16-methyl substituent into 5 alpha -androstane molecules substantially decreases the binding affinity to the androgen receptor and 16 alpha -methyl derivatives were always bound more weakly than the 16 beta -methyl isomers. (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00113-1

文献信息

• Configurational analysis and relative binding affinities of 16-methyl-5α-androstane derivatives
  作者：Pál Tapolcsányi、János Wölfling、István Tóth、Mihály Szécsi、Péter Forgó、Gyula Schneider

  DOI：10.1016/s0039-128x(01)00113-1

  日期：2001.11

  The four possible isomers 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta -dioI 1, 16 alpha -hydroxymethyl-5 alpha -androstane-3 beta ,17 beta -diol 2, 16 beta -hydroxymethyl-5 alpha -androstane-3 beta ,17 alpha -diol 3 and 16 alpha -hydroxymethyl-5 alpha -androstane-3 beta ,17 alpha -diol 4 with proven configuration were converted into the corresponding 16 beta -methyl-5 alpha -androstane-3 beta ,17 beta -dioI 5, 16 alpha -methyl-5 alpha -androstane-3 beta ,17 beta -diol 6, 16 beta -methyl-5 alpha -androstane-3 beta ,17 alpha -diol 7, 16 alpha -methyl-5 alpha -androstane-3 beta ,17 alpha -diol 8, furthermore into the 16 beta -methyl-17 beta -hydroxy-5 alpha -androstane-3-one 13, 16 alpha -methyl-17 beta -hydroxy-5 alpha -androstan-3-one 14, 16 beta -methyl-17 alpha -hydroxy-5 alpha -androstan-3-one 15 and 16 alpha -methyl-17 alpha -hydroxy-5 alpha -androstan-3-one 16. The steric structures of the resulting epimers were determined by means of H-1-, and C-13-NMR spectroscopy. In this way, comparison was possible with the C-16 epimers 5, 6 and 13, 14 prepared earlier by a different route, and the series of isomers could be completed with the steric structures of 16 beta -methyl-17 alpha -hydroxy-5 alpha -androstan-3 beta -ol 7 and 16 alpha -methyl-17 alpha -hydroxy-5 alpha 8 and with their 3-keto derivatives 15 and 16. The relative binding affinities of the 16-methyl-5 alpha -androstane-3 beta ,17-diols 5, 6, 7, 8 and 17-hydroxy-16-methyl-5 alpha -androstan-3-ones 13, 14, 15, 16 were studied. The introduction of a 16-methyl substituent into 5 alpha -androstane molecules substantially decreases the binding affinity to the androgen receptor and 16 alpha -methyl derivatives were always bound more weakly than the 16 beta -methyl isomers. (C) 2001 Elsevier Science Inc. All rights reserved.