(3β,5β,14β,20E)-methyl 14-hydroxyl-21-methylenepregn-21-carboxylate | 86808-61-9

• 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: (3β,5β,14β,20E)-methyl 14-hydroxyl-21-methylenepregn-21-carboxylate
• 英文别名: methyl 3β,14-dihydroxy-21-methylene-5β,14β-pregnane-21-carboxylate
• CAS: 86808-61-9
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: WRJGFXGCRGAQDX-HNQMOXGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3β,5β,14β,20E)-methyl 14-hydroxyl-21-methylenepregn-21-carboxylate 在 silver salicylate 、 barium methoxide 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-Hydroxy-10,13-dimethyl-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-ylmethyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Cardiac glycosides: 2. Synthesis of glucose and galactose analogs

  摘要：

  Five cardioactive steroid genins 1a to 5a of widely varying C17 beta-side groups were converted by modified Koenigs-Knorr reactions into the corresponding beta-D-glucosides 1c to 5c and beta-D-galactosides 1e to 5e. The genins included digitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta-card-20-(22)-enolide, 1a); (20R)-20, 22-dihydrodigitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta, 20R-cardanolde, 2a); 3 beta, 14-dihydroxy-22-methylene-5 beta, 14 beta, 20S-cardanolide (3a); methyl 3 beta, 14-dihydroxy-5 beta, 14 beta-pregn-20(E)-ene-21-carboxylate (4a); and methyl 3 beta, 14-dihydroxy-21-methylene-5 beta, 14 beta-pregnane-21-carboxylate (5a).

  DOI：

  10.1016/s0039-128x(83)90072-7
• 作为产物：
  描述：

  methyl 3β,14-dihydroxy-5β,14β-pregnane-21-carboxylate 在 六甲基二硅氮烷 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 (3β,5β,14β,20E)-methyl 14-hydroxyl-21-methylenepregn-21-carboxylate
  参考文献：
  名称：

  Cardiac glycosides: 2. Synthesis of glucose and galactose analogs

  摘要：

  Five cardioactive steroid genins 1a to 5a of widely varying C17 beta-side groups were converted by modified Koenigs-Knorr reactions into the corresponding beta-D-glucosides 1c to 5c and beta-D-galactosides 1e to 5e. The genins included digitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta-card-20-(22)-enolide, 1a); (20R)-20, 22-dihydrodigitoxigenin (3 beta, 14-dihydroxy-5 beta, 14 beta, 20R-cardanolde, 2a); 3 beta, 14-dihydroxy-22-methylene-5 beta, 14 beta, 20S-cardanolide (3a); methyl 3 beta, 14-dihydroxy-5 beta, 14 beta-pregn-20(E)-ene-21-carboxylate (4a); and methyl 3 beta, 14-dihydroxy-21-methylene-5 beta, 14 beta-pregnane-21-carboxylate (5a).

  DOI：

  10.1016/s0039-128x(83)90072-7