3-[[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-oxopropanoic acid | 189197-31-7

• 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: 3-[[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-oxopropanoic acid
• CAS: 189197-31-7
• 化学式: C₃₀H₄₆O₁₀
• 分子量: 566.689
• InChiKey: ONRFXEPFVIGSCK-QMIJADFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  苯甲醛 、 3-[[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-oxopropanoic acid 在 哌啶 、 4 A molecular sieve 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 (E)-3-Phenyl-acrylic acid (2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-((1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester 、 (Z)-3-Phenyl-acrylic acid (2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-6-oxo-17-((1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Candida antarctica lipase B catalyzes the regioselective esterification of ecdysteroids at the C-2 OH

  摘要：

  Immobilized Candida antarctica lipase B (Novozym 435) catalyzes the regioselective acylation of 20R-hydroxyecdysone (1a) and its congeners 2a, 3a and 4a at the C-2 OH in high yield and purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00245-7
• 作为产物：
  描述：

  1-O-benzyl 3-O-[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] propanedioate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以100%的产率得到3-[[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-oxopropanoic acid
  参考文献：
  名称：

  Candida antarctica lipase B catalyzes the regioselective esterification of ecdysteroids at the C-2 OH

  摘要：

  Immobilized Candida antarctica lipase B (Novozym 435) catalyzes the regioselective acylation of 20R-hydroxyecdysone (1a) and its congeners 2a, 3a and 4a at the C-2 OH in high yield and purity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00245-7