2α,3α-oxo-11-oxo-18b-olean-12-en-29-oic acid | 1234424-54-4

• 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: 2α,3α-oxo-11-oxo-18b-olean-12-en-29-oic acid
• 英文别名: (1R,2S,5S,8S,10R,14R,15S,17R,19S,21R)-1,2,5,8,15,20,20-heptamethyl-13-oxo-18-oxahexacyclo[12.9.0.02,11.05,10.015,21.017,19]tricos-11-ene-8-carboxylic acid
• CAS: 1234424-54-4
• 化学式: C₃₀H₄₄O₄
• 分子量: 468.677
• InChiKey: GWYQOSMROLUBCV-UABVINEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2α,3α-oxo-11-oxo-18b-olean-12-en-29-oic acid 在 N,N-二甲基硫代甲酰胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到2β,3β-epithio-11-oxo-18β-olean-12-en-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：

  11-oxo-18β-oleana-2,12-dien-30-oic acid 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以53.5%的产率得到2α,3α-oxo-11-oxo-18b-olean-12-en-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

文献信息

• Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates
  作者：Hassan Amer、Kurt Mereiter、Christian Stanetty、Andreas Hofinger、Laszlo Czollner、Igor Beseda、Ulrich Jordis、Bernhard Kueenburg、Dirk Claßen-Houben、Paul Kosma

  DOI：10.1016/j.tet.2010.03.098

  日期：2010.6

  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.