4a-methylene-17α-methyl-A-homo-B,19-dinor-5β-androst-9-ene-3β,17-diol | 145458-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4a-methylene-17α-methyl-A-homo-B,19-dinor-5β-androst-9-ene-3β,17-diol
• 英文别名: (5S,8R,10S,11S,14S,15S)-14,15-dimethyl-7-methylidenetetracyclo[8.7.0.02,8.011,15]heptadec-1-ene-5,14-diol
• CAS: 145458-98-6
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: JZICZFMBIMGGDS-PJKJDQBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (5R,6R,8S,13S,14S)-5,13-dimethyl-6-((methylsulfonyl)oxy)-1,2,3,4,5,6,7,8,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl benzoate 在 吡啶 、 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 4a-methylene-17α-methyl-A-homo-B,19-dinor-5β-androst-9-ene-3β,17-diol
  参考文献：
  名称：

  Antihormonal properties of some new A-homo-B, 19-dinor steroids of the androstane series

  摘要：

  On solvolysis of Westphalen-type steroids with a leaving group in the position 6-beta (e.g., 2), products of elimination (followed by rearrangement and fragmentation of the steroid skeleton) were prepared (e.g., 4 and 5). These products were subsequently converted to suitable analogs of the compound, which has been reported to promote hair growth (1). Compounds 11 to 13 exhibited strong antiandrogenic activity in vivo; however, this activity could not be interpreted either in terms of inhibition of 5-alpha-reductase or by strong binding to an androgen receptor.

  DOI：

  10.1016/0039-128x(92)90101-e

文献信息

• Antihormonal properties of some new A-homo-B, 19-dinor steroids of the androstane series
  作者：Alexander Kasal、Richard Hampl、Marie Bičíková、Luboslav Stárka

  DOI：10.1016/0039-128x(92)90101-e

  日期：1992.9

  On solvolysis of Westphalen-type steroids with a leaving group in the position 6-beta (e.g., 2), products of elimination (followed by rearrangement and fragmentation of the steroid skeleton) were prepared (e.g., 4 and 5). These products were subsequently converted to suitable analogs of the compound, which has been reported to promote hair growth (1). Compounds 11 to 13 exhibited strong antiandrogenic activity in vivo; however, this activity could not be interpreted either in terms of inhibition of 5-alpha-reductase or by strong binding to an androgen receptor.