(5alpha,17alpha)-13-乙基-11-亚甲基-18,19-二去甲孕甾-3-烯-20-炔-17-醇 | 201360-82-9

• 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
• 中文名称: (5alpha,17alpha)-13-乙基-11-亚甲基-18,19-二去甲孕甾-3-烯-20-炔-17-醇
• 中文别名: 去氧孕烯Δ3异构体
• 英文名称: 11-methylene-5α,17α-18a-homo-19-nor-pregn-3-en-20-in-17-ol
• 英文别名: desogestrel delta 3-isomer；(5S,8S,9R,10S,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,5,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 201360-82-9
• 化学式: C₂₂H₃₀O
• 分子量: 310.48
• InChiKey: RSMGIILCLKIXNG-JASYKLOUSA-N

物化性质

• 沸点：
  413.4±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  11α,17β-Dihydroxy-18a-homo-estr-4-en-3-one 在 三氧化硫吡啶 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 乙二胺 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二甲基亚砜 、 丙酮 为溶剂， 反应 125.0h， 生成 (5alpha,17alpha)-13-乙基-11-亚甲基-18,19-二去甲孕甾-3-烯-20-炔-17-醇
  参考文献：
  名称：

  The remarkable influence of steroid A/B-ring junction on the Wittig olefination reaction of the 11-oxo group: Towards the synthesis of 5α- and 5β-oriented Δ3-isomers of desogestrel

  摘要：

  The 5 alpha- and 5 beta-oriented Delta(3)-double bond isomers 8, 9 of the widely used progestin desogestrel (7) were synthesized. Wittig olefination reaction of the 5 alpha-intermediate 12 showed a dramatically reduced reaction rate compared with the olefination of the 5 beta-intermediate 13. Computational studies suggest that different energies of the intermediary 1,2-oxaphosphetanes may, at least partially, have been the reason for-this phenomenon. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00105-0

文献信息

• The remarkable influence of steroid A/B-ring junction on the Wittig olefination reaction of the 11-oxo group: Towards the synthesis of 5α- and 5β-oriented Δ3-isomers of desogestrel
  作者：Sven Ring、Gisela Weber、Alexander Hillisch、Sigfrid Schwarz

  DOI：10.1016/s0039-128x(97)00105-0

  日期：1998.1

  The 5 alpha- and 5 beta-oriented Delta(3)-double bond isomers 8, 9 of the widely used progestin desogestrel (7) were synthesized. Wittig olefination reaction of the 5 alpha-intermediate 12 showed a dramatically reduced reaction rate compared with the olefination of the 5 beta-intermediate 13. Computational studies suggest that different energies of the intermediary 1,2-oxaphosphetanes may, at least partially, have been the reason for-this phenomenon. (C) 1998 by Elsevier Science Inc.