(Z)-2-styrylbenzonitrile | 116633-12-6

• 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: (Z)-2-styrylbenzonitrile
• 英文别名: 2-[(Z)-2-phenylethenyl]benzonitrile
• CAS: 116633-12-6
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: USLPZCOPYRKTGY-KHPPLWFESA-N

物化性质

• 熔点：
  39.5-40 °C(Solv: pentane (109-66-0))
• 沸点：
  112-115 °C(Press: 0.2 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  (Z)-2-styrylbenzonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.75h， 生成 2-((Z)-Styryl)-benzylamine
  参考文献：
  名称：

  钯催化未活化烯烃的CH炔基化反应。

  摘要：

  报道了用溴代炔烃和电子无偏烯烃对钯催化的区域和非对映选择性CH官能化。吡啶甲酰胺引导基团能够形成假定的5和6-外金属环化合物作为中间体，以立体特异性方式提供高达91％收率的单炔基化产物。系统的研究表明，在烯烃和溴代炔烃偶合配偶体上具有广泛取代基的底物是可以接受的。证明了所获得的酰胺，烯烃和炔烃的化学选择性转化。

  DOI：

  10.1002/anie.202000935
• 作为产物：
  描述：

  2-(phenylethynyl)benzonitrile 在 乙醇 、 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 联硼酸频那醇酯 、 copper(l) chloride 作用下， 反应 12.0h， 以95%的产率得到(Z)-2-styrylbenzonitrile
  参考文献：
  名称：

  Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

  摘要：

  We herein describe a B(2)Pin(2)-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d(2) in a high deuteration ratio by using readily available ethanol-d(1) as the deuterium source.

  DOI：

  10.1021/acs.joc.9b00321

文献信息

• Carbon-Carbon Cross-Coupling Reactions under Continuous Flow Conditions Using Poly(vinylpyridine) Doped with Palladium
  作者：Andreas Kirschning、Klaas Mennecke、Wladimir Solodenko

  DOI：10.1055/s-2008-1072579

  日期：2008.5

  as Raschig rings or placed within the PASSflow TM microreactor affords technical devices that are well suited for performing palladium-catalyzed carbon-carbon cross-coupling reactions in the flow-through mode. Reusability of the immobilized precatalyst as well as applications in the microwave field were investigated. Experiments with thiol- and pyridine-based scavengers were carried out, which revealed

  将肟基钯环配位固定到形状为拉西环或放置在 PASSflow TM 微反应器中的聚（乙烯基吡啶）/玻璃复合材料上，提供了非常适合在流动中进行钯催化的碳-碳交叉偶联反应的技术设备-直通模式。研究了固定化预催化剂的可重复使用性以及在微波领域的应用。进行了基于硫醇和吡啶的清除剂的实验，结果表明活性钯物质很可能由性质未知的纳米颗粒组成，并且聚（乙烯基吡啶）载体对这些颗粒具有清除性能。
• Selective reduction of alkynes catalyzed by palladium acetate with sodium methoxide as the hydride source
  作者：Li-Lan Wei、Li-Mei Wei、Wen-Bin Pan、Shiow-Piaw Leou、Ming-Jung Wu

  DOI：10.1016/s0040-4039(03)00029-7

  日期：2003.2

  Treatment of internal alkynes with sodium methoxide in the presence of Pd(OAc)2 and PPh3 in methanol for 48 h gave the reduction products, alkenes or alkanes in good chemical yields. This reaction proceeds through a palladium methanolate complex, followed by β-hydride elimination and reductive elimination.

  在甲醇中Pd（OAc）2和PPh 3的存在下，用甲醇钠处理内部炔烃48小时，可以得到具有良好化学收率的还原产物，烯烃或烷烃。该反应通过甲醇钯配合物进行，然后除去β-氢化物并进行还原除去。
• Antiarrhythmic agents. 2-, 3-, and 4-Substituted benzylamines
  作者：David C. Remy、William A. Van Saun、Edward L. Engelhardt、Mary L. Torchiana、Clement A. Stone

  DOI：10.1021/jm00236a006

  日期：1975.2

  The synthesis of a series of 2-, 3-, and 4-substituted benzylamine derivatives is described. These compounds were studied for their effect on experimental cardiac arrhythmias. Many of the derivatives, but in particular 2-(p-methoxyphenylethynyl)benzylamine (3d), alpha,alpha-dimethyl-4y(phenylethynyl)benzylamine (7a), and alpha,alpha-dimethyl-4-phenethylbenzylamine (12g), showed good antiarrhythmic activity.
• The Preparation of and the Spectral Characteristics of Some 2-Substituted cis- and trans-Stilbenes¹
  作者：DeLos F. DeTar、Louis A. Carpino

  DOI：10.1021/ja01583a061

  日期：1956.1
• Palladium‐Catalyzed C−H Alkynylation of Unactivated Alkenes
  作者：Benedikt S. Schreib、Marlene Fadel、Erick M. Carreira

  DOI：10.1002/anie.202000935

  日期：2020.5.11

  Palladium-catalyzed regio- and diastereoselective C-H functionalization with bromoalkynes and electronically unbiased olefins is reported. The picolinamide directing group enables the formation of putative 5 and 6-exo-metallacycles as intermediates to afford monoalkynylated products in up to 91 % yield in a stereospecific fashion. The systematic study reveals that substrates with a wide range of substituents

  报道了用溴代炔烃和电子无偏烯烃对钯催化的区域和非对映选择性CH官能化。吡啶甲酰胺引导基团能够形成假定的5和6-外金属环化合物作为中间体，以立体特异性方式提供高达91％收率的单炔基化产物。系统的研究表明，在烯烃和溴代炔烃偶合配偶体上具有广泛取代基的底物是可以接受的。证明了所获得的酰胺，烯烃和炔烃的化学选择性转化。