(3E,4α)-4-(acetyloxymethyl)-olean-12-en-3-O-acetyloxime | 135322-58-6

• 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: (3E,4α)-4-(acetyloxymethyl)-olean-12-en-3-O-acetyloxime
• 英文别名: [(3E,4S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-3-acetyloxyimino-4,6a,6b,8a,11,11,14b-heptamethyl-2,4a,5,6,7,8,9,10,12,12a,14,14a-dodecahydro-1H-picen-4-yl]methyl acetate
• CAS: 135322-58-6
• 化学式: C₃₄H₅₃NO₄
• 分子量: 539.799
• InChiKey: SJKKBMXNXKQBHU-IHNOPNNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  39.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  64.96
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3E,4α)-4-(acetyloxymethyl)-olean-12-en-3-O-acetyloxime 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 (4S,4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4-Hydroxymethyl-4,6a,6b,8a,11,11,14b-heptamethyl-1,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picen-3-one oxime
  参考文献：
  名称：

  Characterisation of 24-nor-triterpenoids occurring in sediments and crude oils by comparison with synthesized standards

  摘要：

  A series of 24-nor-triterpenoids; 24-nor-urs-12-ene, 24-nor-olean-12-ene and 24-nor-lupane have been identified in sediments and crude oils by comparison with standards obtained by synthesis. A further suite of 24-nor-oleanenes has also been identified by comparison with the acid-catalysed rearrangement products of 24-nor-olean-12-ene. The presence of these components in sedimentary organic matter points to an important new pathway of terrigenous triterpenoid diagenesis.

  DOI：

  10.1016/s0040-4020(01)80903-0
• 作为产物：
  描述：

  乙酸酐 、 olean-12-en-3-one oxime 生成 (3E,4α)-4-(acetyloxymethyl)-olean-12-en-3-O-acetyloxime
  参考文献：
  名称：

  Characterisation of 24-nor-triterpenoids occurring in sediments and crude oils by comparison with synthesized standards

  摘要：

  A series of 24-nor-triterpenoids; 24-nor-urs-12-ene, 24-nor-olean-12-ene and 24-nor-lupane have been identified in sediments and crude oils by comparison with standards obtained by synthesis. A further suite of 24-nor-oleanenes has also been identified by comparison with the acid-catalysed rearrangement products of 24-nor-olean-12-ene. The presence of these components in sedimentary organic matter points to an important new pathway of terrigenous triterpenoid diagenesis.

  DOI：

  10.1016/s0040-4020(01)80903-0

文献信息

• First partial synthesis of α-boswellic acid from oleanolic acid
  作者：Oliver Kraft、Immo Serbian、Ahmed Al-Harrasi、René Csuk

  DOI：10.1016/j.phytol.2022.10.007

  日期：2022.12

  While β-boswellic acid is very readily available by extraction from frankincense resin, the accessibility of α-boswellic from the resin involved great effort and tedious purification procedures. Alternatively, a partial synthesis from readily available oleanolic acid was developed, the key steps of which are a reduction of the carboxyl group C-28 furnishing a methyl group, followed by palladium-assisted

  虽然从乳香树脂中提取 β-乳香酸很容易获得，但从树脂中提取 α-乳香酸需要付出巨大的努力和繁琐的纯化程序。或者，开发了一种从容易获得的齐墩果酸进行部分合成的方法，其关键步骤是还原羧基 C-28 以提供甲基，然后是甲基 C-24 的钯辅助氧化，以及构型反转在 C-3。