16α,17α-cyclohex-3'-eno-16-methylpregn-5-en-3β-ol-20-one acetate | 146303-84-6

• 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-cyclohex-3'-eno-16-methylpregn-5-en-3β-ol-20-one acetate
• CAS: 146303-84-6
• 化学式: C₂₈H₄₀O₃
• 分子量: 424.624
• InChiKey: PWXAUKQORDTQSA-JPNMGIMYSA-N

物化性质

• 沸点：
  503.8±50.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  31.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  16α,17α-cyclohex-3'-eno-16-methylpregn-5-en-3β-ol-20-one acetate 在 Lindlar's catalyst 氢氧化钾 、 氢气 、 aluminum isopropoxide 作用下， 以 甲醇 、 乙醇 、 环己烷 、 水 、 甲苯 为溶剂， 反应 3.5h， 生成 16β-methyl-16α,17α-cyclohexanopregn-4-en-3,20-dione
  参考文献：
  名称：

  Some derivatives of pregna-D6?-pentaranes as possible antagonists of progesterone

  摘要：

  Some derivatives of progestins of the pregna-D-6'-pentarane series have been obtained and examined for their possible hormonal and antihormonal activity in the Clauberg-McPhail assay as well as in the pregnancy maintenance test in ovariectomized rabbits. 16 alpha, 17 alpha-Cyclohexanoprogesterones of the 19-methyl and 19-nor series (1-4) saturated in ring A, which are inactive as progestins, exhibited a remarkable antiprogesterone effect. They decreased the McPhail index under combined administration with progesterone in a dose-dependable manner and completely inhibited the action of the latter in the pregnancy maintenance test.

  DOI：

  10.1007/bf00702407
• 作为产物：
  描述：

  16-甲基-20-氧代孕甾-5,16-二烯-3-beta-基醋酸酯 、 1,3-丁二烯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 40.0 ℃ 、1399.99 MPa 条件下， 反应 5.0h， 以100%的产率得到16α,17α-cyclohex-3'-eno-16-methylpregn-5-en-3β-ol-20-one acetate
  参考文献：
  名称：

  Use of Lewis acids and high pressure to carry out extremely hindered Diels-Alder reactions

  摘要：

  DOI：

  10.1007/bf00958082

文献信息

• 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.