ethyl E-3-[2-(benzofuran-3-yl)phenyl]acrylate | 481071-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl E-3-[2-(benzofuran-3-yl)phenyl]acrylate
• CAS: 481071-94-7
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: CPVPWNNHUGLSHD-VAWYXSNFSA-N

物化性质

• 沸点：
  456.3±38.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  丙烯酸乙酯 、 ethyl E-3-[2-(benzofuran-3-yl)phenyl]acrylate 在 palladium diacetate 、 双二苯基膦甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到ethyl E-3-(3-phenylbenzofuran-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
• 作为产物：
  描述：

  (E,Z)-1-氧代-1,3-二氢异苯并呋喃-5-甲醛肟 在 palladium diacetate 、 甲烷磺酸 、 四丁基氯化铵 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 ethyl E-3-[2-(benzofuran-3-yl)phenyl]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

• 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.