methyl 23-acetoxy-3-(hydroxyimino)olean-12-en-28-oate | 937068-55-8

• 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 23-acetoxy-3-(hydroxyimino)olean-12-en-28-oate
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,9S,10E,12aR,14bS)-9-(acetyloxymethyl)-10-hydroxyimino-2,2,6a,6b,9,12a-hexamethyl-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 937068-55-8
• 化学式: C₃₃H₅₁NO₅
• 分子量: 541.772
• InChiKey: JWGNPYKXIGFLJO-ZUXGUMDQSA-N

物化性质

• 熔点：
  203-205 °C
• 沸点：
  594.3±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  39
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 23-acetoxy-3-(hydroxyimino)olean-12-en-28-oate 在 盐酸 、 sodium tetrahydroborate 、 titanium(III) chloride 、 ammonium acetate 、 lithium bromide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 64.0h， 生成 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：

  3-KETO-齐墩果酸-28-甲酯 在 吡啶 、 盐酸羟胺 作用下， 反应 0.75h， 生成 methyl 23-acetoxy-3-(hydroxyimino)olean-12-en-28-oate
  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