methyl 2α-benzoyloxy-3β-hydroxyolean-12-en-28-oate | 16391-44-9

• 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 2α-benzoyloxy-3β-hydroxyolean-12-en-28-oate
• 英文别名: 2α-Benzoyloxy-3β-hydroxy-oleanen-(12)-saeure-(28)-methylester；methyl (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-benzoyloxy-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 16391-44-9
• 化学式: C₃₈H₅₄O₅
• 分子量: 590.844
• InChiKey: NOTRITKZGOWPNC-DBCDKPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  methyl 2α-benzoyloxy-3β-hydroxyolean-12-en-28-oate 在 吡啶 、 氢氧化钾 、 jones reagent 、 盐酸羟胺 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 methyl 2α,24-dihydroxy-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
• 作为产物：
  描述：

  马斯里酸甲酯 、 苯甲酰氯 在 吡啶 作用下， 反应 0.17h， 以80%的产率得到methyl 2α-benzoyloxy-3β-hydroxyolean-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