5-methyl-19-nor-5β,9β,10β-androstane-3β,17β-diol | 402713-41-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methyl-19-nor-5β,9β,10β-androstane-3β,17β-diol
• 英文别名: (3S,5R,8R,9R,10R,13S,14S,17S)-5,13-dimethyl-2,3,4,6,7,8,9,10,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 402713-41-1
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: JEYKJCVDMVIMAL-HMLCPWEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 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：

  5-methyl-19-nor-5β,9β,10β-androstane-3β,17β-diol 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以93%的产率得到5-methyl-19-nor-5β,9β,10β-androstane-3,17-dione
  参考文献：
  名称：

  Analogues of androgen hormones with inverted configuration at carbons 5, 9, and 10

  摘要：

  On catalytic hydrogenation of Delta (9)-steroids (e.g. 3 beta -hydroxy-5-methyl-19-nor-5 beta -androst-9-en-17-one), four isomers were formed: 9 alpha ,10 alpha-, 9 alpha ,10 beta-, 9 beta ,10 alpha- and 9 beta ,10 beta -adducts. The product distribution was affected by the nature of the C-3 substituent. A chair conformation of A, B, and C rings was found in all of the products with the exception of the 9 alpha ,10 alpha -adduct whose B ring adopts a twist boat conformation. The products were utilized for the synthesis of dihydrotestosterone analogues. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00135-0
• 作为产物：
  描述：

  5-methyl-19-nor-5β-androst-9-ene-3β,17β-diol 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 18.0h， 以61%的产率得到5-methyl-19-nor-5β,9β,10β-androstane-3β,17β-diol
  参考文献：
  名称：

  Analogues of androgen hormones with inverted configuration at carbons 5, 9, and 10

  摘要：

  On catalytic hydrogenation of Delta (9)-steroids (e.g. 3 beta -hydroxy-5-methyl-19-nor-5 beta -androst-9-en-17-one), four isomers were formed: 9 alpha ,10 alpha-, 9 alpha ,10 beta-, 9 beta ,10 alpha- and 9 beta ,10 beta -adducts. The product distribution was affected by the nature of the C-3 substituent. A chair conformation of A, B, and C rings was found in all of the products with the exception of the 9 alpha ,10 alpha -adduct whose B ring adopts a twist boat conformation. The products were utilized for the synthesis of dihydrotestosterone analogues. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00135-0