E-4-oxo-undecadec-2-en-15-olide | 141599-05-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: E-4-oxo-undecadec-2-en-15-olide
• 英文别名: (3E)-16-hexyl-1-oxacyclohexadec-3-ene-2,5-dione
• CAS: 141599-05-5
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: QWAHAFHRIUASNC-ISLYRVAYSA-N

物化性质

• 沸点：
  484.8±24.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  12-羟基硬脂酸 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 E-4-oxo-undecadec-2-en-15-olide
  参考文献：
  名称：

  Intramolecular palladium-catalysed cross coupling; a direct route to γ-Oxo-α,β-unsaturated macrocycles.

  摘要：

  Intramolecular Pd0-catalysed cross coupling of structures terminating in an acyl chloride and a beta-stannylalkenoate has provided a new and an efficient route to 10-20 membered gamma-oxo-alpha,beta-unsaturated macrolides. Both the Z- and E- beta-stannylalkenoates afforded identical macrocylic products demonstrating that under the reaction conditions thermodynamic equilibration of the first formed cross coupled product was most probably occurring. The method has been used to synthesise the macrocyclic framework of the antibiotic A26771B and norpatulolide B.

  DOI：

  10.1016/s0040-4020(01)90977-9

文献信息

• Intramolecular palladium-catalysed cross coupling; a direct route to γ-Oxo-α,β-unsaturated macrocycles.
  作者：Jack E. Baldwin、Robert M. Adlington、Steve H. Ramcharitar

  DOI：10.1016/s0040-4020(01)90977-9

  日期：1992.1

  Intramolecular Pd0-catalysed cross coupling of structures terminating in an acyl chloride and a beta-stannylalkenoate has provided a new and an efficient route to 10-20 membered gamma-oxo-alpha,beta-unsaturated macrolides. Both the Z- and E- beta-stannylalkenoates afforded identical macrocylic products demonstrating that under the reaction conditions thermodynamic equilibration of the first formed cross coupled product was most probably occurring. The method has been used to synthesise the macrocyclic framework of the antibiotic A26771B and norpatulolide B.