ethyl 2-(4-methoxyphenyl)-4-oxo-4-phenylbutanoate | 132566-27-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl 2-(4-methoxyphenyl)-4-oxo-4-phenylbutanoate
• 英文别名: ethyl 2-(4-methoxyphenyl)-4-phenyl-4-oxobutanoate
• CAS: 132566-27-9
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: JFEVVBDJXDISES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  对甲氧基苯乙酸乙酯 在 亚磷酸三苯酯 、 bis(η3-allyl-μ-chloropalladium(II)) diethylzinc 作用下， 以 正己烷 、 氯仿 为溶剂， 反应 11.0h， 生成 ethyl 2-(4-methoxyphenyl)-4-oxo-4-phenylbutanoate
  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

文献信息

• Formation of Five-Membered Cyclic Orthoesters from Tribromides with Participation of a Neighboring Carbonyl Group
  作者：Guddeangadi N. Gururaja、Shaikh M. Mobin、Irishi N. N. Namboothiri

  DOI：10.1002/ejoc.201100042

  日期：2011.4

  but synthetically useful γ-keto esters. The intermediacy of dihydrofurans in the one-pot transformation of keto tribromides into γ-keto esters provides evidence for the active participation of the neighboring carbonyl group in the alcoholysis of the tribromide moiety.

  Mg 介导的溴仿与烯酮的共轭加成，然后所得酮基三溴化物的醇解通过一个不寻常的过程进行，在中性后处理条件下提供环状原酸酯（二氢呋喃）中间体。然而，反应混合物的酸后处理或用酸处理分离的二氢呋喃提供了预期但合成有用的γ-酮酯。二氢呋喃在酮三溴化物一锅转化为 γ-酮酯中的中介作用为相邻羰基积极参与三溴化物部分的醇解提供了证据。
• FUJIMURA, TSUTOMU;AOKI, SATOSHI;NAKAMURA, EIICHI, J. ORG. CHEM., 56,(1991) N, C. 2809-2821
  作者：FUJIMURA, TSUTOMU、AOKI, SATOSHI、NAKAMURA, EIICHI

  DOI：——

  日期：——