methyl 2β-hydroxyolean-12-en-28-oate | 1131502-06-1

• 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: methyl 2β-hydroxyolean-12-en-28-oate
• 英文别名: Methyl 2beta-hydroxyolean-12-en-28-oate；methyl (4aS,6aR,6aS,6bR,8aS,11R,12aS,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1131502-06-1
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: YZOLGBVVXTYMTM-WHOKMKORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2β-hydroxyolean-12-en-28-oate 在 吡啶 、 三氯氧磷 作用下， 反应 0.5h， 以92%的产率得到methyl 2,12-oleandien-28-oate
  参考文献：
  名称：

  Different pathways for the deoxygenation of the A-ring of natural triterpene compounds

  摘要：

  Some deoxygenation pathways were tested to remove the hydroxyl groups of the natural triterpenes oleanolic acid and maslinic acid to obtain a practical starting material for the semisynthesis of other interesting organic synthons. Different deoxygenation processes were carried out starting from these triterpenic acids or from several derivatives such as methyl esters and epoxy derivatives. The hydroxyl groups were transformed into some intermediate compounds including xanthyl, thiocarbonyl or tosyl derivatives. The opening of the oxirane ring between C-2 and C-3 was also achieved through different methods using deoxygenating reagents such as Me3SiCl/NaI, WCl4/n-BuLi and Cp2TiCl.

  DOI：

  10.1080/14786410903172098
• 作为产物：
  描述：

  methyl 2β,3β-epoxy-12-oleanen-28-oate 在 二氯二茂钛 、 锰 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以82%的产率得到methyl 2,12-oleandien-28-oate
  参考文献：
  名称：

  Different pathways for the deoxygenation of the A-ring of natural triterpene compounds

  摘要：

  Some deoxygenation pathways were tested to remove the hydroxyl groups of the natural triterpenes oleanolic acid and maslinic acid to obtain a practical starting material for the semisynthesis of other interesting organic synthons. Different deoxygenation processes were carried out starting from these triterpenic acids or from several derivatives such as methyl esters and epoxy derivatives. The hydroxyl groups were transformed into some intermediate compounds including xanthyl, thiocarbonyl or tosyl derivatives. The opening of the oxirane ring between C-2 and C-3 was also achieved through different methods using deoxygenating reagents such as Me3SiCl/NaI, WCl4/n-BuLi and Cp2TiCl.

  DOI：

  10.1080/14786410903172098

文献信息

• Synthesis of 3-Deoxypentacyclic Triterpene Derivatives as Inhibitors of Glycogen Phosphorylase
  作者：Pu Zhang、Jia Hao、Jun Liu、Qian Lu、Huaming Sheng、Luyong Zhang、Hongbin Sun

  DOI：10.1021/np9002367

  日期：2009.8.28

  3-deoxy-2-keto derivatives 5 and 7 of oleanolic acid (1) and ursolic acid (2), respectively, served as precursors to the synthesis of 35 3-deoxy derivatives of pentacyclic triterpenes. The synthesized compounds were biologically assayed for their inhibitory activity against rabbit muscle glycogen phosphorylase a (GPa). Among this series of compounds, 2α-hydroxyurs-12-en-28-oic acid (18) (IC50 = 1.2

  齐墩果酸（1）和熊果酸（2）的3-脱氧-2-酮衍生物5和7分别用作合成五环三萜的35个3-脱氧衍生物的前体。生物学分析了合成的化合物对兔肌肉糖原磷酸化酶a（GPa）的抑制活性。在这一系列化合物中，2α-羟基urs-12-en-28-油酸（18）（IC 50 = 1.2μM）表现出最强的活性。初步讨论了3-脱氧三萜衍生物作为GP抑制剂的构效关系分析。
• Different pathways for the deoxygenation of the A-ring of natural triterpene compounds
  作者：Andres Parra、Pilar E. Lopez、Andres Garcia-Granados

  DOI：10.1080/14786410903172098

  日期：2010.1.20

  Some deoxygenation pathways were tested to remove the hydroxyl groups of the natural triterpenes oleanolic acid and maslinic acid to obtain a practical starting material for the semisynthesis of other interesting organic synthons. Different deoxygenation processes were carried out starting from these triterpenic acids or from several derivatives such as methyl esters and epoxy derivatives. The hydroxyl groups were transformed into some intermediate compounds including xanthyl, thiocarbonyl or tosyl derivatives. The opening of the oxirane ring between C-2 and C-3 was also achieved through different methods using deoxygenating reagents such as Me3SiCl/NaI, WCl4/n-BuLi and Cp2TiCl.