ethyl E-3-(4-nitrobiphen-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-nitrobiphen-2-yl)acrylate
• 英文别名: ethyl (E)-3-(5-nitro-2-phenylphenyl)prop-2-enoate
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: HISCSHMHZXWBIC-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-1-碘-4-硝基苯 在 palladium diacetate 、 四(三苯基膦)钯 sodium carbonate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 ethyl E-3-(4-nitrobiphen-2-yl)acrylate
  参考文献：
  名称：

  C−H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions

  摘要：

  [GRAPHICS]Biaryl bromides such as 1 (R=NO2, H, OMe) undergo the Heck reaction to give both the expected products 3 ("retention") as well as "crossover" products 4 derived from a migration of Pd and net transfer of reactivity from one aryl ring to the other. Under the conditions used, crossover is increasingly favored when electron-deficient arenes are involved. Crossover products derived from transfer onto the pyridine ring have also been observed.

  DOI：

  10.1021/ol026426v

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.
• C−H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions
  作者：Gunter Karig、Maria-Teresa Moon、Nopporn Thasana、Timothy Gallagher

  DOI：10.1021/ol026426v

  日期：2002.9.1

  [GRAPHICS]Biaryl bromides such as 1 (R=NO2, H, OMe) undergo the Heck reaction to give both the expected products 3 ("retention") as well as "crossover" products 4 derived from a migration of Pd and net transfer of reactivity from one aryl ring to the other. Under the conditions used, crossover is increasingly favored when electron-deficient arenes are involved. Crossover products derived from transfer onto the pyridine ring have also been observed.