methyl (4aS,6aS,6bR,8aS,11S,12aS,12bR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate | 1226871-94-8

• 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 (4aS,6aS,6bR,8aS,11S,12aS,12bR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
• CAS: 1226871-94-8
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: YZOLGBVVXTYMTM-CYVYTNFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.32
• 重原子数：
  34.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 methyl (4aS,6aS,6bR,8aS,11S,12aS,12bR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以80%的产率得到methyl (4aS,6aS,6bR,8aS,11S,12aS,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-11-(((methylthio)carbonothioyl)oxy)-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
  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 (4aS,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-11-((tert-butyldimethylsilyl)oxy)-2,2,6a,6b,9,9,12a-heptamethyl-10-(((methylthio)carbonothioyl)oxy)-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate 在 偶氮二异丁腈 、 亚膦酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以40%的产率得到methyl (4aS,6aS,6bR,8aS,11S,12aS,12bR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylate
  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