ethyl 2-methyl-4-oxopentadecanoate | 132566-34-8

• 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: ethyl 2-methyl-4-oxopentadecanoate
• CAS: 132566-34-8
• 化学式: C₁₈H₃₄O₃
• 分子量: 298.466
• InChiKey: NGYMGGLEYHIDPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  21.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  月桂酰氯 、 1-Ethoxy-2-methyl-1-(trimethylsilyloxy)cyclopropan 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 氯仿 为溶剂， 反应 22.0h， 以37%的产率得到ethyl 2-methyl-4-oxopentadecanoate
  参考文献：
  名称：

  Synthesis of 1,4-keto esters and 1,4-diketones via palladium-catalyzed acylation of siloxycyclopropanes. Synthetic and mechanistic studies

  摘要：

  The reaction of a variety of siloxycyclopropanes with acid chlorides in the presence of a catalytic amount of a palladium/phosphine complex gives 1,4-dicarbonyl compounds to good yield. 1-Alkoxy-1-(trialkylsiloxy)-cyclopropanes react with both aromatic and aliphatic acid chlorides in chloroform to give 1,4-keto esters. Synthesis of 1,4-diketones by the acylation of 1-alkyl- or 1-aryl-1-siloxycyclopropanes has been achieved by carrying out the reaction if HMPA under 10-20 atm of carbon monoxide. Kinetics studies and product analysis revealed the unique mechanism of this reaction, which involves rate-determining cleavage of the strained cyclopropane carbon-carbon bond with a coordinatively unsaturated acylpalladium chloride complex. Ab initio calculations of hydroxylated cyclopropane model compounds showed that the unique reactivities of the siloxycyclopropanes may be correlated with the molecular orbital properties of these compounds rather than their ground-state structural properties.

  DOI：

  10.1021/jo00008a043