[(3S,4aR,6aR,6aR,6bR,8aR,12R,12aR,14aR,14bR)-8a-(acetyloxymethyl)-12-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl] 2,2-dimethylpropanoate | 1000296-77-4

• 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: [(3S,4aR,6aR,6aR,6bR,8aR,12R,12aR,14aR,14bR)-8a-(acetyloxymethyl)-12-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl] 2,2-dimethylpropanoate
• CAS: 1000296-77-4
• 化学式: C₃₇H₆₂O₅
• 分子量: 586.896
• InChiKey: BDGIKQAYZNANCC-LIEVKJJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3S,4aR,6aR,6aR,6bR,8aR,12R,12aR,14aR,14bR)-8a-(acetyloxymethyl)-12-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl] 2,2-dimethylpropanoate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  Useful approach to access germanicanes from betulin

  摘要：

  A new semisynthetic access to germanicane-type triterpenes was achieved from betulin, a natural triterpene of the lupane family. The Wagner-Meerwein rearrangement of acetylated betulinic acid allowed the formation of the typical ring E of germanicanes and a lactone function. Several germanicane derivatives can be obtained via the lactone ring-opening such as 19 beta-machaerocerol and 19 beta-machaeroceric acid. The cytotoxicity of some compounds was evaluated against two cancerous cell lines. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.171
• 作为产物：
  描述：

  [(1R,4aR,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bR)-1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicen-4a-yl]methyl acetate 、 三甲基乙酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以96%的产率得到[(3S,4aR,6aR,6aR,6bR,8aR,12R,12aR,14aR,14bR)-8a-(acetyloxymethyl)-12-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Useful approach to access germanicanes from betulin

  摘要：

  A new semisynthetic access to germanicane-type triterpenes was achieved from betulin, a natural triterpene of the lupane family. The Wagner-Meerwein rearrangement of acetylated betulinic acid allowed the formation of the typical ring E of germanicanes and a lactone function. Several germanicane derivatives can be obtained via the lactone ring-opening such as 19 beta-machaerocerol and 19 beta-machaeroceric acid. The cytotoxicity of some compounds was evaluated against two cancerous cell lines. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.171