methyl 2α,24-dihydroxy-3-oxoolean-12-en-28-oate | 937068-89-8

• 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 2α,24-dihydroxy-3-oxoolean-12-en-28-oate
• 英文别名: methyl (4aS,6aR,6aS,6bR,8aR,9S,11R,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 937068-89-8
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: JVFNZRJYXLCCKR-IYZKTYDYSA-N

物化性质

• 沸点：
  588.3±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2α,24-dihydroxy-3-oxoolean-12-en-28-oate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-2,3-diol
  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：

  methyl 2α-acetoxy-3β-hydroxyolean-12-en-28-oate 在 吡啶 、 盐酸 、 氢氧化钾 、 jones reagent 、 titanium(III) chloride 、 盐酸羟胺 、 ammonium acetate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 7.0h， 生成 methyl 2α,24-dihydroxy-3-oxoolean-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