(1R,4aR,4bS,6R,8aS,10aR)-6-(acetyloxy)tetradecahydro-2-oxo-1-phenanthrenepropanenitrile | 948563-41-5

• 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: (1R,4aR,4bS,6R,8aS,10aR)-6-(acetyloxy)tetradecahydro-2-oxo-1-phenanthrenepropanenitrile
• 英文别名: [(3R,4aS,4bR,8R,8aR,10aS)-8-(2-cyanoethyl)-7-oxo-2,3,4,4a,4b,5,6,8,8a,9,10,10a-dodecahydro-1H-phenanthren-3-yl] acetate
• CAS: 948563-41-5
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: NRFOLQPYITYQIW-OBRKIGFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4aR,4bS,6R,8aS,10aR)-6-(acetyloxy)tetradecahydro-2-oxo-1-phenanthrenepropanenitrile 在 三氢化钐 、 碘 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 (2β,5α,13ξ,14β)-2-(acetyloxy)-13-hydroxy-18-norestran-17-one
  参考文献：
  名称：

  Neurosteroid analogues. Part 13: Synthetic methods for the preparation of 2β-hydroxygonane derivatives as structural mimics of ent-3α-hydroxysteroid modulators of GABAA receptors

  摘要：

  Many different 3 alpha-hydroxysteroids in the androstane and pregnane steroid series enhance the actions of gamma-aminobutyric acid (GABA) at GABA type-A (GABA(A)) receptors in the mammalian central nervous system. Recent studies have shown that (3 alpha,5 alpha)-3-hydroxy-androstan-17- one (androsterone) is less active at these receptors than its enantiomer ent-androsterone. Further structure-activity relationship (SAR) studies are needed to explore the structural features of ent-androsterone that are important for its enhanced action at these receptors. Molecular modeling shows that 2 beta-hydroxysteroids are similar in three-dimensional shape to the enantiomers of 3 alpha-hydroxysteroids. The development of synthetic methods to gain access to C-17-substituted analogues of 2 beta-hydroxygonanes for SAR studies is demonstrated with the synthesis of (2 beta,5 alpha,14 beta)-2-hydroxygonan-17-one. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.068
• 作为产物：
  描述：

  (3S,5S,8R,9R,10S,13S,14R)-13-methylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 三氢化钐 、 sodium tetrahydroborate 、 盐酸羟胺 、 水 、 碘 、 sodium acetate 、 对甲苯磺酸 、 臭氧 、 pyridinium chlorochromate 、 三氟乙酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 39.91h， 生成 (1R,4aR,4bS,6R,8aS,10aR)-6-(acetyloxy)tetradecahydro-2-oxo-1-phenanthrenepropanenitrile
  参考文献：
  名称：

  Neurosteroid analogues. Part 13: Synthetic methods for the preparation of 2β-hydroxygonane derivatives as structural mimics of ent-3α-hydroxysteroid modulators of GABAA receptors

  摘要：

  Many different 3 alpha-hydroxysteroids in the androstane and pregnane steroid series enhance the actions of gamma-aminobutyric acid (GABA) at GABA type-A (GABA(A)) receptors in the mammalian central nervous system. Recent studies have shown that (3 alpha,5 alpha)-3-hydroxy-androstan-17- one (androsterone) is less active at these receptors than its enantiomer ent-androsterone. Further structure-activity relationship (SAR) studies are needed to explore the structural features of ent-androsterone that are important for its enhanced action at these receptors. Molecular modeling shows that 2 beta-hydroxysteroids are similar in three-dimensional shape to the enantiomers of 3 alpha-hydroxysteroids. The development of synthetic methods to gain access to C-17-substituted analogues of 2 beta-hydroxygonanes for SAR studies is demonstrated with the synthesis of (2 beta,5 alpha,14 beta)-2-hydroxygonan-17-one. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.068