methyl (7-propiolate)-heptanoate | 137097-28-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (7-propiolate)-heptanoate
• 英文别名: Methyl 7-prop-2-ynoyloxyheptanoate
• CAS: 137097-28-0
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: YKCFIYWWNXIBPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (7-propiolate)-heptanoate 生成 Z-4-oxo-dec-2-en-10-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
• 作为产物：
  描述：

  oxocan-2-one 在 三氟化硼乙醚 、 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 methyl (7-propiolate)-heptanoate
  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。