16α,17α-cyclohexanopregna-1,4-diene-3,20-dione | 39987-92-3

• 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: 16α,17α-cyclohexanopregna-1,4-diene-3,20-dione
• 英文别名: (4aR,4bS,6aS,6bS,10aR,11aS,11bS)-6b-acetyl-4a,6a-dimethyl-5,6,7,8,9,10,10a,11,11a,11b,12,13-dodecahydro-4bH-indeno[2,1-a]phenanthren-2-one
• CAS: 39987-92-3
• 化学式: C₂₅H₃₄O₂
• 分子量: 366.544
• InChiKey: CZKXJQWZMJXDRU-IEHCJHDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16α,17α-cyclohexanopregna-1,4-diene-3,20-dione 、 2,3-二甲基-1,3-丁二烯 在 三氯化铝 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、1499.99 MPa 条件下， 反应 5.0h， 生成 4',5'-dimethyl-4α,5α-cyclohex-4'-eno-16α,17α-cyclohexanopregn-1-ene-3,20-dione 、 3',4'-dimethyl-1α,2α-cyclohex-3'-eno-16α,17α-cyclohexanopregn-4-ene-3,20-dione
  参考文献：
  名称：

  Catalysis by lewis acids at high pressure as a method of involving hindered steroid dienophiles in the diels?Alder reaction

  摘要：

  The joint action of Lewis acids and high pressure permits the Diels-Alder reaction to be conducted with high yields with greatly sterically hindered steroid dienophiles, which are virtually unreactive under normal conditions. The [2 + 4]-cycloadditions of dienes to DELTA16-20-, DELTA1-3-, DELTA1,4-3-, and DELTA4,6-3-ketones proceed stereospecifically with the formation of one stereoisomer for each cycloadduct. The reactions of the steroid dienes studied give mixtures of two monocycloadducts at both double bonds of the steroid, with predominance of the adduct at the sterically less-hindered double bond (DELTA1- and DELTA6-). The method developed is a new method of producing various modified steroids with possible hormonal or antihormonal activity.

  DOI：

  10.1007/bf00864191
• 作为产物：
  描述：

  (16beta,17alpha)-17-乙酰基-16,24-环-21-去甲胆-4-烯-3-酮 在 苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 10.0h， 以76%的产率得到16α,17α-cyclohexanopregna-1,4-diene-3,20-dione
  参考文献：
  名称：

  Catalysis by lewis acids at high pressure as a method of involving hindered steroid dienophiles in the diels?Alder reaction

  摘要：

  The joint action of Lewis acids and high pressure permits the Diels-Alder reaction to be conducted with high yields with greatly sterically hindered steroid dienophiles, which are virtually unreactive under normal conditions. The [2 + 4]-cycloadditions of dienes to DELTA16-20-, DELTA1-3-, DELTA1,4-3-, and DELTA4,6-3-ketones proceed stereospecifically with the formation of one stereoisomer for each cycloadduct. The reactions of the steroid dienes studied give mixtures of two monocycloadducts at both double bonds of the steroid, with predominance of the adduct at the sterically less-hindered double bond (DELTA1- and DELTA6-). The method developed is a new method of producing various modified steroids with possible hormonal or antihormonal activity.

  DOI：

  10.1007/bf00864191