3α-acetyloxy-11-oxo-18β-olean-1,12-dien-29-oic acid | 1234424-59-9

• 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: 3α-acetyloxy-11-oxo-18β-olean-1,12-dien-29-oic acid
• CAS: 1234424-59-9
• 化学式: C₃₂H₄₆O₅
• 分子量: 510.714
• InChiKey: LBJGWMSZMYBBMP-WYIAZCPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  37.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3α-acetyloxy-11-oxo-18β-olean-1,12-dien-29-oic acid 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以87%的产率得到3α-hydroxy-11-oxo-18β-olean-1,12-dien-29-oic acid
  参考文献：
  名称：

  Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates

  摘要：

  A general method for the introduction of thiol groups at positions 1, 2, and 3 of glycyrrhetinic acid has been developed starting from a protected 2 alpha,3 alpha-oxido-derivative. Conversion into the corresponding 2 beta,3 beta-epithio-derivative was followed by ring-opening leading to either 2- or 3-substituted thio derivatives. Conversely, 3 alpha-configured allylic alcohol intermediates derived from the 2,3-epoxide provided efficient access to both diastereoisomeric 3-thio derivatives as well as 1 alpha-thio derivatives. The stereochemistry of the newly formed stereogenic centers was rigorously proven using X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.098
• 作为产物：
  描述：

  3α-acetyloxy-2β-iodo-11-oxo-18β-olean-12-en-29-oic acid 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 以72%的产率得到3α-acetyloxy-11-oxo-18β-olean-1,12-dien-29-oic acid
  参考文献：
  名称：

  Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates

  摘要：

  A general method for the introduction of thiol groups at positions 1, 2, and 3 of glycyrrhetinic acid has been developed starting from a protected 2 alpha,3 alpha-oxido-derivative. Conversion into the corresponding 2 beta,3 beta-epithio-derivative was followed by ring-opening leading to either 2- or 3-substituted thio derivatives. Conversely, 3 alpha-configured allylic alcohol intermediates derived from the 2,3-epoxide provided efficient access to both diastereoisomeric 3-thio derivatives as well as 1 alpha-thio derivatives. The stereochemistry of the newly formed stereogenic centers was rigorously proven using X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.098