[(3R,5S,8R,9R,10S,13S,14R)-13-methyl-2-oxospiro[1,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-yl] acetate | 948563-29-9

• 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: [(3R,5S,8R,9R,10S,13S,14R)-13-methyl-2-oxospiro[1,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-yl] acetate
• CAS: 948563-29-9
• 化学式: C₂₂H₃₂O₅
• 分子量: 376.493
• InChiKey: ISRNTYWFZWOGSW-RNPSNPMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3R,5S,8R,9R,10S,13S,14R)-13-methyl-2-oxospiro[1,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-yl] acetate 在 三氢化钐 、 碘 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.25h， 生成 (2R,5S,8R,9R,10S,13S,14R)-13-methylhexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-2-ol
  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 、 sodium tetrahydroborate 、 sodium acetate 、 臭氧 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 25.08h， 生成 [(3R,5S,8R,9R,10S,13S,14R)-13-methyl-2-oxospiro[1,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-yl] acetate
  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