diphenylmethyl 2α,3α-oxo-11-oxo-18β-olean-12-en-29-oate | 1234424-53-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diphenylmethyl 2α,3α-oxo-11-oxo-18β-olean-12-en-29-oate
• CAS: 1234424-53-3
• 化学式: C₄₃H₅₄O₄
• 分子量: 634.899
• InChiKey: VNHDEKKQZOPTFP-JEQCGJGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.68
• 重原子数：
  47.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.9
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 2α,3α-oxo-11-oxo-18β-olean-12-en-29-oate 在 三氟乙酸 、 sodium methylate 、 10% palladium on carbon 、 氢气 作用下， 以 甲苯 、 甲醇 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以70%的产率得到2β,3α-dihydroxy-11-carbonyloleanorane-12-ene-30-carboxylic 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：

  diphenylmethyl 11-oxo-18β-olean-2,12-dien-29-oate 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到diphenylmethyl 2α,3α-oxo-11-oxo-18β-olean-12-en-29-oate
  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