(E)-3-(4-acetylphenyl)acrylonitrile | 77120-12-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-(4-acetylphenyl)acrylonitrile
• 英文别名: (E)-3-(4-acetylphenyl)prop-2-enenitrile
• CAS: 77120-12-8
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: UEMPYFVSMFETOF-NSCUHMNNSA-N

物化性质

• 熔点：
  84-86 °C
• 沸点：
  351.8±25.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-3-(4-acetylphenyl)-2-propen-1-ol acetate 在 四(三苯基膦)钯 、 叠氮基三甲基硅烷 、 sulfur 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 (E)-3-(4-acetylphenyl)acrylonitrile
  参考文献：
  名称：

  从烯丙基酯中提取烯基腈的有效方法

  摘要：

  已开发出一种从烯丙基酯中提取烯基腈的新型有效方法。该转化过程涉及Pd催化的串联取代和随后的氧化重排。该方法为烯丙酯合成烯基腈提供了重要的补充。

  DOI：

  10.1055/s-0030-1259719

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。
• Design and Development of a New Chelating Bis(phosphinite)-Based Palladium(II) Catalyst and Its Application to the Heck Reaction
  作者：D. Pathak、H. Maheswaran、K. Prasanth、M. Kantam

  DOI：10.1055/s-2007-970750

  日期：2007.3

  A new sterically demanding and bulky bis(phosphinite) ligand derived from salicylaldehyde and 2-amino-3-hydroxy ­pyridine and its palladium(II) complex has been synthesized and characterized. The utility of this palladium complex has been de­monstrated in the Heck reaction between a variety of aryl halides and olefin substrates.

  一种由水杨醛和2-氨基-3-羟基吡啶衍生得到的新型立体位阻大且体积庞大的双(膦酰)配体及其钯(II)配合物已被合成并表征。该钯配合物在各种芳基卤化物与烯烃底物的 Heck 反应中的实用性已得到展示。
• Mizoroki-Heck cross-couplings of 2-acetyl-5-bromobenzofuran and aryl halides under microwave irradiation
  作者：Mohamed R. Shaaban、Ahmed F. Darweesh、Kamal M. Dawood、Ahmad M. Farag

  DOI：10.3998/ark.5550190.0011.a18

  日期：——

  Mizoroki-Heck cross-coupling reactions of 2-acetyl-5-bromobenzofuran as well as activated and deactivated aryl bromides with various olefins were investigated under both thermal as well as microwave irradiating conditions in open air using water solvent.

  研究了 2-乙酰基-5-溴苯并呋喃以及活化和失活的芳基溴化物与各种烯烃的 Mizoroki-Heck 交叉偶联反应，在露天使用水溶剂的热和微波辐射条件下进行了研究。
• Multi-functionalized ionic liquid with in situ-generated palladium nanoparticles for Suzuki, Heck coupling reaction: a comparison with deep eutectic solvents
  作者：D. S. Gaikwad、K. A. Undale、D. B. Patil、D. M. Pore

  DOI：10.1007/s13738-018-1503-z

  日期：2019.2

  without using external phosphine ligand. Along with electron deficient olefins, electron rich olefins were also undergo smooth reaction giving excellent yield. The results obtained in ionic liquid are compared with results obtained in deep eutectic solvents. Progress of reaction was found very smooth in ionic liquid rather than in deep eutectic solvents. The aqueous system containing ionic liquid along

  摘要从多功能任务特定离子液体（TSIL）和原位形成的钯纳米粒子（PdNps）开发了一种用于Suzuki和Heck偶联的新催化系统。通过紫外可见光谱和透射电子显微镜（TEM）分析对生成的PdNP进行表征。这些PdNPs的尺寸小于10 nm，并且在不使用外部膦配体的情况下，在芳基卤化物的交叉偶联中表现出出色的催化活性。与贫电子的烯烃一起，富电子的烯烃也经历了平滑的反应，从而获得了优异的收率。将在离子液体中获得的结果与在深共熔溶剂中获得的结果进行比较。发现在离子液体中而不是在深共熔溶剂中反应进展非常顺利。 图形概要
• Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction
  作者：Hui Wu、Can Jin、GuoLi Huang、LianJun Wang、JuLi Jiang、LeYong Wang

  DOI：10.1007/s11426-011-4272-4

  日期：2011.6

  Two new bis-imidazolinium salts (4a, 4b) have been synthesized as precursors of N-heterocyclic carbenes (NHCs) from the commercially available (R)-2,2′-dihydroxy-1,1′-binaphthalene. The two bis-imidazolinium salts were used as efficient precursor of NHC ancillary ligands in the palladium-catalyzed Heck reaction. Good to excellent yields and high stereoselectivities were obtained with ethyl acrylate, acrylonitrile, and acrylamide as starting materials. The structure of bis-imidazolinium salt 4b was further characterized by single crystal X-ray diffraction analysis.

  两种新的双咪唑铵盐（4a，4b）作为N-杂环氮烯（NHC）的前体已合成，这些材料来源于商业可得的（R）-2,2′-二羟基-1,1′-联萘。这两种双咪唑铵盐在钯催化的Heck反应中作为NHC辅助配体的高效前体。使用乙基丙烯酸酯、丙烯腈和丙烯酰胺作为起始材料时，获得了良好至优异的产率和高选择性。双咪唑铵盐4b的结构进一步通过单晶X射线衍射分析进行了表征。