ethyl E-3-(4'-methylbiphen-2-yl)acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl E-3-(4'-methylbiphen-2-yl)acrylate
• 英文别名: ethyl (E)-3-[2-(4-methylphenyl)phenyl]prop-2-enoate
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: PSRATOXUMUNUMQ-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-碘-4'-甲基联苯 、 丙烯酸乙酯 在 palladium diacetate 、 四丁基氯化铵 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以100%的产率得到ethyl E-3-(4'-methylbiphen-2-yl)acrylate
  参考文献：
  名称：

  Novel 1,4-Palladium Migration in Organopalladium Intermediates Derived from o-Iodobiaryls

  摘要：

  A novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryls has been observed under modified Heck reaction conditions. This migration process can be switched "on" or "off" by simply choosing the appropriate reaction conditions.

  DOI：

  10.1021/ja027548l

文献信息

• Sequential Difunctionalization of 2-Iodobiphenyls by Exploiting the Reactivities of a Palladacycle and an Acyclic Arylpalladium Species
  作者：Dushen Chen、Guangfa Shi、Hang Jiang、Yu Zhang、Yanghui Zhang

  DOI：10.1021/acs.orglett.6b00753

  日期：2016.5.6

  A novel sequential difunctionalization reaction of 2-iodobiphenyl has been developed by exploiting the distinct reactivities of a palladacycle and an acyclic arylpalladium species. In this tandem reaction, an in situ formed dibenzopalladacyclopentadiene reacts selectively with an alkyl halide, after which the thus formed acyclic arylpalladium species selectively undergoes a Heck reaction with an alkene

  通过利用palladacycle和无环芳基钯物种的独特反应性，开发了2-碘联苯的新型顺序双官能化反应。在该串联反应中，原位形成的二苯并钯铝环戊二烯与卤代烷选择性地反应，此后，由此形成的无环芳基钯物质选择性地与烯烃进行Heck反应。这项工作证明了过渡金属络合物的配位模式与其反应性之间的密切关系，可以揭示其他过渡金属催化的反应机理，并为开发其他合成实现的有机转化提供机会。
• Novel 1,4-Palladium Migration in Organopalladium Intermediates Derived from <i>o</i>-Iodobiaryls
  作者：Marino A. Campo、Richard C. Larock

  DOI：10.1021/ja027548l

  日期：2002.12.1

  A novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryls has been observed under modified Heck reaction conditions. This migration process can be switched "on" or "off" by simply choosing the appropriate reaction conditions.
• US6150413A
  申请人：——

  公开号：US6150413A

  公开（公告）日：2000-11-21
• Aryl to Aryl Palladium Migration in the Heck and Suzuki Coupling of <i>o</i>-Halobiaryls
  作者：Marino A. Campo、Haiming Zhang、Tuanli Yao、Abdellatif Ibdah、Ryan D. McCulla、Qinhua Huang、Jian Zhao、William S. Jenks、Richard C. Larock

  DOI：10.1021/ja069238z

  日期：2007.5.1

  A novel 1,4-palladium migration between the o- and o'-positions of biaryls has been observed in organopalladium intermediates derived from o-halobiaryls. The organopalladium intermediates generated by this migration have been trapped either by a Heck reaction employing ethyl acrylate or by Suzuki cross-coupling using arylboronic acids. This palladium migration can be activated or deactivated by choosing the appropriate reaction conditions. Chemical and computational evidence supports the presence of an equilibrium that correlates with the C-H acidity of the available arene positions.