(3aS,5aS,6R,9aR,9bS)-3a-ethyl-6-(3-oxobutyl)decahydro-3H-cyclopenta[a]naphthalene-3,7(3aH)-dione | 23759-68-4

• 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
• 英文名称: (3aS,5aS,6R,9aR,9bS)-3a-ethyl-6-(3-oxobutyl)decahydro-3H-cyclopenta[a]naphthalene-3,7(3aH)-dione
• CAS: 23759-68-4；35442-20-7；38852-16-3
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: XDWBHIQODWFBFZ-RGQDEETRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aS,5aS,6R,9aR,9bS)-3a-ethyl-6-(3-oxobutyl)decahydro-3H-cyclopenta[a]naphthalene-3,7(3aH)-dione 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 生成 18-甲基-4-雌烯-3,17-二酮
  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：

  (4aS,6aS)-6a-ethyl-11a-hydroxy-2-methyltetradecahydroindeno[5,4-f]chromen-7(8H)-one 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 (3aS,5aS,6R,9aR,9bS)-3a-ethyl-6-(3-oxobutyl)decahydro-3H-cyclopenta[a]naphthalene-3,7(3aH)-dione
  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