20-oxo-30-nortaraxastan-3β-yl acetate | 22415-32-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 20-oxo-30-nortaraxastan-3β-yl acetate
• 英文别名: 3β-acetoxy-20-oxo-30-nortaraxastane；[(3S,4aR,6aR,6aR,6bR,8aS,12S,12aS,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-oxo-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-yl] acetate
• CAS: 22415-32-3
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: IQZXDTWCPZRBPX-DWZJQIMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  20-oxo-30-nortaraxastan-3β-yl acetate 在 selenium(IV) oxide 、 双氧水 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以65.5%的产率得到21-oxo-20-oxa-30-nor-22a-homotaraxastan-3β-yl acetate
  参考文献：
  名称：

  Synthesis and transformations of 20-oxo-30-nortaraxasteryl acetate derivatives

  摘要：

  20,20-Dimethoxy-, Delta(21)-20-oxo-, and 20-oxo-30-nortaraxasteryl acetates were synthesized by selective ozonolysis of taraxasteryl acetate. Baeyer-Villiger oxidation of 20-oxo-30-nortaraxasteryl acetate with SeO2-H2O2 gave 3 beta-acetoxytaraxa-(19,20)-epsilon-lactone. Mechanism of the ozonolysis of taraxasteryl acetate is discussed. The enthalpies of formation of possible intermediates were calculated by quantum-chemical methods, and most favorable paths of the ozonolysis and dehydrogenation were determined.

  DOI：

  10.1134/s1070428007030050
• 作为产物：
  描述：

  蒲公英甾醇醋酸酯 在 水 、 对甲苯磺酸 、 臭氧 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 72.0h， 生成 20-oxo-30-nortaraxastan-3β-yl acetate
  参考文献：
  名称：

  Synthesis and transformations of 20-oxo-30-nortaraxasteryl acetate derivatives

  摘要：

  20,20-Dimethoxy-, Delta(21)-20-oxo-, and 20-oxo-30-nortaraxasteryl acetates were synthesized by selective ozonolysis of taraxasteryl acetate. Baeyer-Villiger oxidation of 20-oxo-30-nortaraxasteryl acetate with SeO2-H2O2 gave 3 beta-acetoxytaraxa-(19,20)-epsilon-lactone. Mechanism of the ozonolysis of taraxasteryl acetate is discussed. The enthalpies of formation of possible intermediates were calculated by quantum-chemical methods, and most favorable paths of the ozonolysis and dehydrogenation were determined.

  DOI：

  10.1134/s1070428007030050