(3R,3aS,5aS,9aR,9bS)-3a-Ethyl-3-ethynyl-3-hydroxy-6-(3-hydroxy-butyl)-dodecahydro-cyclopenta[a]naphthalen-7-one O-methyl-oxime | 30155-35-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,3aS,5aS,9aR,9bS)-3a-Ethyl-3-ethynyl-3-hydroxy-6-(3-hydroxy-butyl)-dodecahydro-cyclopenta[a]naphthalen-7-one O-methyl-oxime
• CAS: 30155-35-2
• 化学式: C₂₂H₃₅NO₃
• 分子量: 361.525
• InChiKey: ODDYYEUSXPALSS-WVNASXILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  62.05
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R,3aS,5aS,9aR,9bS)-3a-Ethyl-3-ethynyl-3-hydroxy-6-(3-hydroxy-butyl)-dodecahydro-cyclopenta[a]naphthalen-7-one O-methyl-oxime 在 chromium(VI) oxide 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,3aS,5aS,9aR,9bS)-3a-Ethyl-3-ethynyl-3-hydroxy-6-(3-oxo-butyl)-dodecahydro-cyclopenta[a]naphthalen-7-one O-methyl-oxime
  参考文献：
  名称：

  [类固醇全合成。IV。（+）-13-乙基-17-乙炔基-17-羟基-gon-4-en-3-one]。

  摘要：

  AbstractThe title compound (Norgestrel), a potent progestational agent, has been prepared by a new total synthesis. The scheme is based on earlier work with BCD‐tricyclic intermediates, condensation of 2‐ethyl‐cyclopentane‐1,3‐dione with 2‐[2‐diethylamino‐ethyl]‐6‐[4‐t‐butoxy‐pentyl]‐tetrahydropyran‐2‐ol being the key step. The synthesis features the addition of acetylene to a Δ5(10)‐4‐oxa‐17‐keto intermediate, followed by a novel transformation to the final product.

  DOI：

  10.1002/hlca.19710540852
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 (8S,9R,13R,14R,17S)-13-Ethyl-17-ethynyl-3-methyl-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-4-oxa-cyclopenta[a]phenanthren-17-ol 在 吡啶 作用下， 以 水 为溶剂， 生成 (3R,3aS,5aS,9aR,9bS)-3a-Ethyl-3-ethynyl-3-hydroxy-6-(3-hydroxy-butyl)-dodecahydro-cyclopenta[a]naphthalen-7-one O-methyl-oxime
  参考文献：
  名称：

  [类固醇全合成。IV。（+）-13-乙基-17-乙炔基-17-羟基-gon-4-en-3-one]。

  摘要：

  AbstractThe title compound (Norgestrel), a potent progestational agent, has been prepared by a new total synthesis. The scheme is based on earlier work with BCD‐tricyclic intermediates, condensation of 2‐ethyl‐cyclopentane‐1,3‐dione with 2‐[2‐diethylamino‐ethyl]‐6‐[4‐t‐butoxy‐pentyl]‐tetrahydropyran‐2‐ol being the key step. The synthesis features the addition of acetylene to a Δ5(10)‐4‐oxa‐17‐keto intermediate, followed by a novel transformation to the final product.

  DOI：

  10.1002/hlca.19710540852