3α-hydroxy-5,6β-epoxy-7-nor-5β-pregnan-20-one | 286862-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 3α-hydroxy-5,6β-epoxy-7-nor-5β-pregnan-20-one
• 英文别名: 1-[(1S,2R,4S,6R,9R,10S,13S,14S,17S)-6-hydroxy-9,13-dimethyl-3-oxapentacyclo[8.7.0.02,4.04,9.013,17]heptadecan-14-yl]ethanone
• CAS: 286862-36-0
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: XCJFPPWIIUINAO-KLJREVGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-hydroxy-5,6β-epoxy-7-nor-5β-pregnan-20-one 在 三氟化硼乙醚 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以88%的产率得到3α-hydroxy-7-nor-5α-pregnane-6,20-dione
  参考文献：
  名称：

  Epalons: 6-Substituted Derivatives of 7-Norepiallopregnanolone

  摘要：

  The target compounds (3 alpha-hydroxy-5,6-epoxy-7-nor-5 alpha-pregnan-20-one, 3 alpha-hydroxy-5,6 beta-epoxy-7-nor-5 beta-pregnan-20-one and 3 alpha-hydroxy-7-nor-5 alpha-pregnane-6,20-dione) were prepared from 5,6 beta-dihydroxy-20-oxo-5 alpha-pregnan-3 beta-yl acetate via the corresponding 5,6-seco acid and 3 beta-acetoxy-20-oxo-7-nor-5 beta,6 alpha-pregnane-6,5-carbolactone-actone. Intermediate 3 beta-hydroxy-7-norpregn-5-en-20-one was converted into the corresponding 5 alpha,6 alpha and 5 beta,6 beta epoxides. The latter was isomerized into 3 beta-hydroxy-7-nor-5 alpha-pregnane-6,20-dione. The configuration of the 3 beta-hydroxy group in these compounds was inverted by Mitsunobu reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00263-5
• 作为产物：
  描述：

  3β-hydroxy-5,6β-epoxy-7-nor-5β-pregnan-20-one 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 3α-hydroxy-5,6β-epoxy-7-nor-5β-pregnan-20-one
  参考文献：
  名称：

  Epalons: 6-Substituted Derivatives of 7-Norepiallopregnanolone

  摘要：

  The target compounds (3 alpha-hydroxy-5,6-epoxy-7-nor-5 alpha-pregnan-20-one, 3 alpha-hydroxy-5,6 beta-epoxy-7-nor-5 beta-pregnan-20-one and 3 alpha-hydroxy-7-nor-5 alpha-pregnane-6,20-dione) were prepared from 5,6 beta-dihydroxy-20-oxo-5 alpha-pregnan-3 beta-yl acetate via the corresponding 5,6-seco acid and 3 beta-acetoxy-20-oxo-7-nor-5 beta,6 alpha-pregnane-6,5-carbolactone-actone. Intermediate 3 beta-hydroxy-7-norpregn-5-en-20-one was converted into the corresponding 5 alpha,6 alpha and 5 beta,6 beta epoxides. The latter was isomerized into 3 beta-hydroxy-7-nor-5 alpha-pregnane-6,20-dione. The configuration of the 3 beta-hydroxy group in these compounds was inverted by Mitsunobu reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00263-5

文献信息

• Epalons: 6-Substituted Derivatives of 7-Norepiallopregnanolone
  作者：Alexander Kasal

  DOI：10.1016/s0040-4020(00)00263-5

  日期：2000.5

  The target compounds (3 alpha-hydroxy-5,6-epoxy-7-nor-5 alpha-pregnan-20-one, 3 alpha-hydroxy-5,6 beta-epoxy-7-nor-5 beta-pregnan-20-one and 3 alpha-hydroxy-7-nor-5 alpha-pregnane-6,20-dione) were prepared from 5,6 beta-dihydroxy-20-oxo-5 alpha-pregnan-3 beta-yl acetate via the corresponding 5,6-seco acid and 3 beta-acetoxy-20-oxo-7-nor-5 beta,6 alpha-pregnane-6,5-carbolactone-actone. Intermediate 3 beta-hydroxy-7-norpregn-5-en-20-one was converted into the corresponding 5 alpha,6 alpha and 5 beta,6 beta epoxides. The latter was isomerized into 3 beta-hydroxy-7-nor-5 alpha-pregnane-6,20-dione. The configuration of the 3 beta-hydroxy group in these compounds was inverted by Mitsunobu reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.