(3S,5R,8R,9S,10R,13S,14S,15S,16S,17S)-17-(3-Hydroxy-propyl)-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-2H-cyclopropa[15,16]cyclopenta[a]phenanthrene-3,5,17-triol | 108664-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5R,8R,9S,10R,13S,14S,15S,16S,17S)-17-(3-Hydroxy-propyl)-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-2H-cyclopropa[15,16]cyclopenta[a]phenanthrene-3,5,17-triol
• 英文别名: (1R,2S,3S,5S,6S,7S,10S,11R,14S,16R)-6-(3-hydroxypropyl)-7,11-dimethylpentacyclo[8.8.0.02,7.03,5.011,16]octadec-17-ene-6,14,16-triol
• CAS: 108664-95-5
• 化学式: C₂₃H₃₆O₄
• 分子量: 376.536
• InChiKey: UZTSAJIFBPWAIG-ZLWSQXOLSA-N

物化性质

• 沸点：
  535.9±50.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  80.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,5R,8R,9S,10R,13S,14S,15S,16S,17S)-17-(3-Hydroxy-propyl)-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-2H-cyclopropa[15,16]cyclopenta[a]phenanthrene-3,5,17-triol 在 吡啶 、 chromium(VI) oxide 、 水 作用下， 反应 18.0h， 生成 6,7-去亚甲基-6,7-去氢屈螺酮
  参考文献：
  名称：

  Aldosterone antagonists. 2. New 7.alpha.-(acetylthio)-15,16-methylene spirolactones

  摘要：

  Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of spironolactone.

  DOI：

  10.1021/jm00391a023
• 作为产物：
  描述：

  (3b,5b,15a,16a)-15,16-二氢-3,5-二羟基-3’H-环丙并[15,16]雄甾-6,15-二烯-17-酮 在 镍 potassium ethoxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (3S,5R,8R,9S,10R,13S,14S,15S,16S,17S)-17-(3-Hydroxy-propyl)-10,13-dimethyl-1,3,4,8,9,10,11,12,13,14,15,16,17,20-tetradecahydro-2H-cyclopropa[15,16]cyclopenta[a]phenanthrene-3,5,17-triol
  参考文献：
  名称：

  Aldosterone antagonists. 2. New 7.alpha.-(acetylthio)-15,16-methylene spirolactones

  摘要：

  Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of spironolactone.

  DOI：

  10.1021/jm00391a023