(E)-cinnamyl (E)-2,4-dimethoxycinnamate | 1027770-98-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-cinnamyl (E)-2,4-dimethoxycinnamate
• 英文别名: (E)-cinnamyl 3-(2,4-dimethoxyphenyl)acrylate；[(E)-3-phenylprop-2-enyl] (E)-3-(2,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1027770-98-4
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: HLHMKUXIIQUABJ-PDEGXQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  烯丙苯 、 反-2,4-二甲氧基肉桂酸 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 苯基-P-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以72%的产率得到(E)-cinnamyl (E)-2,4-dimethoxycinnamate
  参考文献：
  名称：

  Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation

  摘要：

  A highly general, predictably selective C H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (1 6 examples, EIZ L- 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C H oxidation vs C C bond-forming methods are evaluated and discussed in four "case studies".

  DOI：

  10.1021/ja104826g

文献信息

• Mahajan, Rajesh P; Patil, Ulhas K; Patil, Shamkant L, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 9, p. 1459 - 1465
  作者：Mahajan, Rajesh P、Patil, Ulhas K、Patil, Shamkant L

  DOI：——

  日期：——
• Synthesis of Complex Allylic Esters via C−H Oxidation vs C−C Bond Formation
  作者：Nicolaas A. Vermeulen、Jared H. Delcamp、M. Christina White

  DOI：10.1021/ja104826g

  日期：2010.8.18

  A highly general, predictably selective C H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (1 6 examples, EIZ L- 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C H oxidation vs C C bond-forming methods are evaluated and discussed in four "case studies".