16α,17α-cyclohexane-5α-pregn-1-ene-3,20-dione | 122605-80-5

• 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-cyclohexane-5α-pregn-1-ene-3,20-dione
• 英文别名: 16α,17α-cyclohexano-5α-pregn-1-ene-3,20-diole；(4aR,4bS,6aS,6bS,10aR,11aS,11bR,13aS)-6b-acetyl-4a,6a-dimethyl-4b,5,6,7,8,9,10,10a,11,11a,11b,12,13,13a-tetradecahydro-1H-indeno[2,1-a]phenanthren-2-one
• CAS: 122605-80-5
• 化学式: C₂₅H₃₆O₂
• 分子量: 368.56
• InChiKey: UUFJYBWQFMWSQT-QRSGIJRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 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-cyclohexane-5α-pregn-1-ene-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， 以85%的产率得到3',4'-dimethyl-1α,2α-cyclohex-3'-eno-16α,17α-cyclohexano-5α-pregnane-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：

  16α,17α-cyclohexane-5α-pregnane-3β-ol-20-one acetate 在 氢氧化钾 、 jones' reagent 、 pyridinium hydrobromide perbromide 、 calcium carbonate 作用下， 以 甲醇 、 N,N-二甲基乙酰胺 、 溶剂黄146 、 丙酮 为溶剂， 反应 1.66h， 生成 16α,17α-cyclohexane-5α-pregn-1-ene-3,20-dione
  参考文献：
  名称：

  Biological activity of transformed steroids

  摘要：

  DOI：

  10.1007/bf00771697

文献信息

• Use of Lewis acids and high pressure to carry out extremely hindered Diels-Alder reactions
  作者：B. S. �l'yanov、I. S. Levina、L. E. Kulikova、A. V. Kamernitskii、E. M. Gonikberg

  DOI：10.1007/bf00958082

  日期：1989.3
• Catalysis by lewis acids at high pressure as a method of involving hindered steroid dienophiles in the diels?Alder reaction
  作者：I. S. Levina、L. E. Kulikova、A. V. Kamernitskii、B. S. El'yanov、E. M. Gonikberg

  DOI：10.1007/bf00864191

  日期：1992.7

  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.
• Biological activity of transformed steroids
  作者：A. V. Kamernitskii、I. S. Levina、L. E. Kulikova、G. V. Nikitina、V. V. Korkhov

  DOI：10.1007/bf00771697

  日期：1990.3