(3S,5S,8R,9S,10S,13S,14S)-17-((S)-4-hydroxybutan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 1040364-33-7

• 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: (3S,5S,8R,9S,10S,13S,14S)-17-((S)-4-hydroxybutan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
• CAS: 1040364-33-7
• 化学式: C₂₅H₄₀O₃
• 分子量: 388.591
• InChiKey: ZIJMURGBBPWOOJ-VGKDHJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,5S,8R,9S,10S,13S,14S)-17-((S)-4-hydroxybutan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 在 盐酸 、 5% Pd/C 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以12 mg的产率得到(3S,5S,8R,9S,10S,13R,14S,17R)-17-((S)-4-hydroxybutan-2-yl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
  参考文献：
  名称：

  Ligand Tuning in Asymmetric Hydrovinylation of 1,3-Dienes: A Stereoselective Route to Either Steroid-C₂₀ (S) or -C₂₀ (R) Derivatives

  摘要：

  1,3-Dienes derived from steroidal D-ring C(17)-ketones undergo Ni(II)-catalyzed hydrovinylation to give 1,2- or 1,4-addition of ethylene. Using finely tuned phosphoramidite ligands, it is possible to synthesize either the C(20) (R)- or (S)-derivatives without mutual contamination. The proportion of the 1,4-adduct, which is also formed stereoselectively, can be minimized by optimizing the reaction conditions. Because the two alkenes in the resultant dienes have differing steric demands for many potential reactions, and are ideally juxtaposed for further D-ring functionalization, these intermediates could be useful for the preparation of biologically important compounds such as vitamin D analogs and various antitumor steroidal glycosides.

  DOI：

  10.1021/ja711475f
• 作为产物：
  描述：

  乙烯 、 (3S,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-vinyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 在 bi(allylnickel bromide) 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 N,N-双-((S)-1-苯基乙基)二苯并[d,f][1,3,2]二氧杂膦-6-胺 、 9-borabicyclo[3.3.1]nonane dimer 、 氢氧化钾 、 双氧水 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 (3S,5S,8R,9S,10S,13S,14S)-17-((S)-4-hydroxybutan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
  参考文献：
  名称：

  Ligand Tuning in Asymmetric Hydrovinylation of 1,3-Dienes: A Stereoselective Route to Either Steroid-C₂₀ (S) or -C₂₀ (R) Derivatives

  摘要：

  1,3-Dienes derived from steroidal D-ring C(17)-ketones undergo Ni(II)-catalyzed hydrovinylation to give 1,2- or 1,4-addition of ethylene. Using finely tuned phosphoramidite ligands, it is possible to synthesize either the C(20) (R)- or (S)-derivatives without mutual contamination. The proportion of the 1,4-adduct, which is also formed stereoselectively, can be minimized by optimizing the reaction conditions. Because the two alkenes in the resultant dienes have differing steric demands for many potential reactions, and are ideally juxtaposed for further D-ring functionalization, these intermediates could be useful for the preparation of biologically important compounds such as vitamin D analogs and various antitumor steroidal glycosides.

  DOI：

  10.1021/ja711475f