Hederagenin-methylester-3-acetat | 19906-52-6

• 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: Hederagenin-methylester-3-acetat
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-acetyloxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 19906-52-6
• 化学式: C₃₃H₅₂O₅
• 分子量: 528.773
• InChiKey: BBSROZNIKZQFCD-ZTCCBMIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  Hederagenin-methylester-3-acetat 在 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到常春藤皂苷元
  参考文献：
  名称：

  Remote Hydroxylation of Methyl Groups by Regioselective Cyclopalladation. Partial Synthesis of Hyptatic Acid-A

  摘要：

  Hyptatic acid-A (32), a 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

  DOI：

  10.1021/jo070116e
• 作为产物：
  描述：

  oxime of methyl oleanonate 在 盐酸 、 sodium tetrahydroborate 、 titanium(III) chloride 、 ammonium acetate 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 16.0h， 生成 Hederagenin-methylester-3-acetat
  参考文献：
  名称：

  Remote Hydroxylation of Methyl Groups by Regioselective Cyclopalladation. Partial Synthesis of Hyptatic Acid-A

  摘要：

  Hyptatic acid-A (32), a 2 alpha,3 beta,24-trihydroxyolean-12-en-28-oic acid, previously isolated from Hyptis capitata, was obtained from maslinic acid (2). The regioselective cyclopalladation of the axial methyl group on C-4 of maslinic acid afforded the C-24 hydroxymethylene group due to the presence of a C-2-OR substituent. Nevertheless, hederagenin (7) (23-hydroxy derivative) was formed when this oxygenated group was not present.

  DOI：

  10.1021/jo070116e