(E)-4-(1,2-diphenylvinyl)benzonitrile | 1020073-95-3

• 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: (E)-4-(1,2-diphenylvinyl)benzonitrile
• 英文别名: 4-[(E)-1,2-diphenylethenyl]benzonitrile
• CAS: 1020073-95-3
• 化学式: C₂₁H₁₅N
• 分子量: 281.357
• InChiKey: YCRVQKPHOGSLIO-RCCKNPSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-bromo-1,2-diphenylethene 在 potassium phosphate 、 二(三叔丁基膦)钯 、 仲丁基锂 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 环己烷 、 水 为溶剂， 反应 12.01h， 生成 (E)-4-(1,2-diphenylvinyl)benzonitrile
  参考文献：
  名称：

  通过精确控制流动中顺式-反式异构化的区域选择性合成α-官能的苯乙烯类化合物

  摘要：

  通过使用流动微反应器可选择性地控制α-阴离子的快速顺式-反式异构化，并使其与各种亲电试剂进行反应。将反应时间精确控制在-50°C的毫秒至秒之间，以高收率选择性地产生顺式或反式异构体。这种流动的合成方法被很好地用于合成具有高区域选择性和生产率的商品药物化合物（E）-和（Z）-他莫昔芬的前体。

  DOI：

  10.1021/acs.orglett.1c00538

文献信息

• Employing Water as the Hydride Source in Synthesis: A Case Study of Diboron Mediated Alkyne Hydroarylation
  作者：Santhosh Rao、M. Nibin Joy、Kandikere Ramaiah Prabhu

  DOI：10.1021/acs.joc.8b01965

  日期：2018.11.16

  We present an approach to utilize water as the hydride source via Pd(II)/Pd(0) catalysis. As a case study, we have achieved a diboron mediated Pd(II)-catalyzed hydroarylation of alkynes using arylboronic acids. This approach not only complements conventional reactivity of Pd via Pd(0)/Pd(II) cycle for the hydroarylation but also utilizes water as the hydride source. We believe this would particularly

  我们提出一种通过Pd（II）/ Pd（0）催化利用水作为氢化物来源的方法。作为一个案例研究，我们已经实现了使用芳基硼酸的二硼介导的Pd（II）催化炔烃的氢芳基化反应。该方法不仅通过Pd（0）/ Pd（II）循环对Pd的常规反应性进行了补充，还可以利用水作为氢化物源。我们认为，这对于利用水作为试剂特别有益。
• Straightforward Iron-Catalyzed Synthesis of Vinylboronates by the Hydroboration of Alkynes
  作者：Michael Haberberger、Stephan Enthaler

  DOI：10.1002/asia.201200931

  日期：2013.1

  An iron‐catalyzed hydroboration of alkynes to produce vinylboronates has been examined. With a straightforward system composed of iron carbonyls and pinacolborane, good to excellent yields and chemoselectivities were achieved for a variety of alkynes.

  已经研究了炔烃的铁催化硼氢化反应以生产乙烯基硼酸酯。有了由羰基铁和频哪醇硼烷组成的简单体系，各种炔烃的收率和化学选择性都达到了极佳的水平。
• Palladium-Catalyzed Hydroarylation of Alkynes with Arenediazonium Salts
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Daniela Persiani

  DOI：10.1021/ol800266e

  日期：2008.4.1

  The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (2)-2-arylcinnamates stereo- and regioselectively.
• Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid <i>cis</i>–<i>trans</i> Isomerization in Flow
  作者：Hyune-Jea Lee、Yuya Yonekura、Nayoung Kim、Jun-ichi Yoshida、Heejin Kim

  DOI：10.1021/acs.orglett.1c00538

  日期：2021.4.16

  The rapid cis–trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at −50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial

  通过使用流动微反应器可选择性地控制α-阴离子的快速顺式-反式异构化，并使其与各种亲电试剂进行反应。将反应时间精确控制在-50°C的毫秒至秒之间，以高收率选择性地产生顺式或反式异构体。这种流动的合成方法被很好地用于合成具有高区域选择性和生产率的商品药物化合物（E）-和（Z）-他莫昔芬的前体。