methyl 3α-hydroxy-12α-acetyloxy-7α-(D-prolyl)amino-5β-cholan-24-oate | 1070884-40-0

• 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: methyl 3α-hydroxy-12α-acetyloxy-7α-(D-prolyl)amino-5β-cholan-24-oate
• CAS: 1070884-40-0
• 化学式: C₃₂H₅₂N₂O₆
• 分子量: 560.775
• InChiKey: ZEOHDMNBTKGPGD-DISDAZCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  113.96
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  methyl 3α,12α-diacetyloxy-7α-N-(D-prolinoyl)amino-5β-cholan-24-oate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到methyl 3α-hydroxy-12α-acetyloxy-7α-(D-prolyl)amino-5β-cholan-24-oate
  参考文献：
  名称：

  Substrate control by means of the chiral cavity of prolinamide derivatives of cholic acid in the organocatalyzed Michael addition of cyclohexanone to nitroolefins

  摘要：

  Different prolinamide and bis-prolinamide derivatives were checked as organocatalysts in the asymmetric Michael addition of cyclohexanone to aromatic nitroolefins, and the derivative bearing a D-prolinamide moiety linked at the 7-position emerged as the most efficient, giving the Michael adducts in satisfactory yield and ees of up to 95%. The corresponding system having a free CH group at the 3-position of the cholestanic backbone afforded the opposite enantiomer of the product, suggesting that the transition state is developed at the inner part of the cholestanic cavity, which is responsible for the substrate control determining the stereochemical outcome of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.018