1,2-diphenyl-1-(p-ethaneoylphenyl)ethene | 93080-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-diphenyl-1-(p-ethaneoylphenyl)ethene
• 英文别名: 1,2-diphenyl-1-(p-ethanoylphenyl)ethene；1-[4-(1,2-Diphenylethenyl)phenyl]ethanone；1-[4-(1,2-diphenylethenyl)phenyl]ethanone
• CAS: 93080-11-6
• 化学式: C₂₂H₁₈O
• 分子量: 298.384
• InChiKey: VLNZXMQCKQAWMD-UHFFFAOYSA-N

物化性质

• 沸点：
  433.3±24.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-碘代苯乙酮 、 二苯乙烯 在 silver tetrafluoroborate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以51%的产率得到1,2-diphenyl-1-(p-ethaneoylphenyl)ethene
  参考文献：
  名称：

  卤化物的银螯合活化Pd（OAc）2催化1,1和1,2-二取代烯烃的Mizoroki-Heck反应

  摘要：

  由Pd（OAc）2（cat）和化学计量的银盐AgOAc或AgBF 4组成的无配体催化体系在Mizoroki-Heck芳基化反应中表现出高效率，可转化芳基碘化物和1,1以及1,2在非常短的反应时间内，双取代的烯烃就可以以优异的收率转化成1,1,2-三取代的芳基烯烃。

  DOI：

  10.1002/aoc.4159

文献信息

• Pd-catalyzed Heck reactions of aryl bromides with 1,2-diarylethenes
  作者：Jones Limberger、Silvia Poersch、Adriano L Monteiro

  DOI：10.1590/s0103-50532011000700026

  日期：——

  A catalytic system composed of Pd(OAc)(2) and P(o-tol)(3) was found to be effective for the Heck reaction of aryl bromides with diarylethylenes. Using K(2)CO(3) as a base and DMF as a solvent, trisubstituted olefins were obtained in good to excellent yields. Aryl bromides containing an electron-withdrawing group in para position were less reactive for the Heck coupling reaction and gave substantial amount of homocoupling by-product suggesting that oxidative addition is not the rate-determining step. Electron withdrawing group substituent in the para position of stilbene affects the regioselectivity of the reaction. In this case, the phenyl group from the Ph-Pd complex migrates preferentially to the same carbon of the double bond to which the phenyl is bonded. Finally, a one pot sequential double Heck arylation of styrene was performed, giving trisubstituted olefin with an overall yield of 73%.
• Silver sequestration of halides for the activation of Pd(OAc) ₂ catalyzed Mizoroki‐Heck reaction of 1,1 and 1,2 ‐ Disubstituted alkenes
  作者：Pronnoy G. Bangar、Priyanka R. Jawalkar、Swapnil R. Dumbre、Dharmaraj J. Patil、Suresh Iyer

  DOI：10.1002/aoc.4159

  日期：2018.3

  A ligand free catalytic system consisting of Pd(OAc)2 (cat) and stoichiometric quantities of silver salts, AgOAc or AgBF4, exhibit high efficiency in the Mizoroki‐Heck arylation, transforming aryl iodides and 1,1 as well as 1,2 disubstituted alkenes into 1,1,2 – trisubstituted aryl alkenes in excellent yields in very short reaction times.

  由Pd（OAc）2（cat）和化学计量的银盐AgOAc或AgBF 4组成的无配体催化体系在Mizoroki-Heck芳基化反应中表现出高效率，可转化芳基碘化物和1,1以及1,2在非常短的反应时间内，双取代的烯烃就可以以优异的收率转化成1,1,2-三取代的芳基烯烃。