E-4-oxo-tridec-2-en-13-olide | 137097-55-3

• 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-tridec-2-en-13-olide
• 英文别名: E-oxacyclotetradec-3-ene-2,5-dione；(3E)-1-oxacyclotetradec-3-ene-2,5-dione
• CAS: 137097-55-3
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: BQDKSOWTPXXWEL-MDZDMXLPSA-N

物化性质

• 沸点：
  389.5±21.0 °C(Predicted)
• 密度：
  0.993±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  10-羟基癸酸 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-tridec-2-en-13-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 route to γ-oxo-α,β-unsaturated macrocycles
  作者：Jack E. Baldwin、Robert M. Adlington、Steve H. Ramcharitar

  DOI：10.1039/c39910000940

  日期：——

  A new and relatively simple method involving Pd0-catalysed cross coupling of acid chlorides and β-stannyl alkenoates provides an efficient route to γ-oxo-α,β-unsaturated macrolides.

  一种相对简单的新方法涉及 Pd0 催化的酸氯化物与 δ²-stannyl 烯酸酯的交叉偶联，为获得 δ³-氧代-δ±,δ²-不饱和大环内酯提供了一条有效途径。
• Ring Expansions of β-Keto Lactones with Zinc Carbenoids:  Syntheses of (+)-Patulolide A and (±)-Patulolide B
  作者：Matthew D. Ronsheim、Charles K. Zercher

  DOI：10.1021/jo0264776

  日期：2003.3.1

  A one-pot ring expansion/oxidation/elimination method has been developed in which beta-keto lactones are converted efficiently to alpha,beta-unsaturated-gamma-keto lactones. The reaction can be successfully applied to a variety of ring sizes. Alkene stereochemistry is dependent upon ring size and reaction conditions. The method was applied to the synthesis of (+)-patulolide A.

  已经开发了一种一锅环膨胀/氧化/消除方法，其中β-酮内酯被有效地转化为α，β-不饱和-γ-酮内酯。该反应可以成功地应用于各种环尺寸。烯烃的立体化学取决于环的大小和反应条件。该方法适用于（+）-广pat香酚A的合成。
• 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.