(Z)-1,2-diphenyl-1-pentamethylphenylethene

• 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)-1,2-diphenyl-1-pentamethylphenylethene
• 英文别名: 1-[(Z)-1,2-diphenylethenyl]-2,3,4,5,6-pentamethylbenzene
• 化学式: C₂₅H₂₆
• 分子量: 326.481
• InChiKey: HBOYLUDSENUSQQ-JLPGSUDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  五甲基苯 、 二苯基乙炔 在 silver tetrafluoroborate 、 tetrafluoroboric acid 、 3,3′-bis(methyl)-[(1,1′-diibenzmidazolin-2,2′-diylidene) 1,1′-methylene] palladium(II) dibromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以12%的产率得到(Z)-1,2-diphenyl-1-pentamethylphenylethene
  参考文献：
  名称：

  炔烃氢化芳基化与螯合二卡宾钯 (II) 络合物催化剂：添加剂筛选后发现的改进和意外反应模式

  摘要：

  发现钯 (II) 与由螯合 N-杂环双卡宾配体和两个弱配位阴离子（通常在添加 2 当量合适的银盐后原位引入）制成的配体组的配合物是非常活跃和选择性的催化剂在低催化剂负载量 (0.1 mol-%) 下炔烃的室温加氢芳基化。此外，各种强酸作为反应促进剂的筛选表明，酸的强度和其共轭碱的配位能力都会影响催化性能。最显着的是，HBF4 与二卡宾 Pd 络合物催化剂一起使用使反应的选择性发生了巨大变化，由于两分子炔烃插入芳族 C-H 键，产物的普遍形成。本文中呈现的结果强调了这样一个事实，即双卡宾配体除了稳定催化剂外，还能够提高催化活性，最值得注意的是，将反应选择性导向新产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900321

文献信息

• Metal-Free Hydroarylation of Alkynes: A Very Convenient, Simple Procedure for Substituted Arylalkenes
  作者：Tsugio Kitamura、Md. Ataur Rahman、Osamu Ogawa、Juzo Oyamada

  DOI：10.1055/s-0028-1083635

  日期：2008.12

  Hydroarylation of aryl-substituted alkynes with simple and substituted arenes was conducted in the presence of trifluoroacetic acid in dichloromethane without any metal catalysts or additives. Electron-rich arenes coupled with aryl-substituted alkynes to give 1,1-diarylalkenes in good to high yields.

  在氯仿中，使用三氟乙酸在没有任何金属催化剂或添加剂的情况下，对芳基取代的炔烃与简单和取代的芳烃进行了氢聚合反应。电子丰富的芳烃与芳基取代的炔烃偶联，生成了1,1-二芳基烯烃，产率良好至较高。
• Thermodynamically- and kinetically-controlled Friedel–Crafts alkenylation of arenes with alkynes using an acidic fluoroantimonate(v) ionic liquid as catalyst
  作者：Doo Seong Choi、Jin Hong Kim、Ueon Sang Shin、Ravindra R. Deshmukh、Choong Eui Song

  DOI：10.1039/b705719a

  日期：——

  By employing superacidic fluoroantimonate ionic liquid (IL), [bmim][Sb2F11], as catalyst, not only thermodynamically-controlled but also kinetically-controlled Friedel–Crafts alkenylations of arenes with alkynes have been realized for the first time.

  通过采用超酸性氟锑酸离子液体（IL）[bmim][Sb2F11]作为催化剂，首次实现了既受热力学控制又受动力学控制的芳香族化合物与炔烃的Friedel-Crafts烯基化反应。
• Metal Triflate-Catalyzed Regio- and Stereoselective Friedel–Crafts Alkenylation of Arenes with Alkynes in an Ionic Liquid: Scope and Mechanism
  作者：Mi Young Yoon、Jin Hong Kim、Doo Seoung Choi、Ueon Sang Shin、Jin Yong Lee、Choong Eui Song

  DOI：10.1002/adsc.200700039

  日期：2007.7.2

  In the metal triflate-catalyzed hydroarylation of alkynes, employing an ionic liquid dramatically enhanced the catalytic activities, resulting in broadening the scope of substrates (arenes and alkynes). In some cases, even reactions that were not possible in conventional organic solvents proceeded smoothly in ionic liquids. Moreover, the ionic liquid phase containing catalyst could be readily recovered

  在金属三氟甲磺酸酯催化的炔烃加氢芳基化中，采用离子液体显着增强了催化活性，从而扩大了底物（芳烃和炔烃）的范围。在某些情况下，甚至在常规有机溶剂中不可能发生的反应在离子液体中也能顺利进行。而且，通过在反应后简单地倾析有机层，可以容易地回收含离子液体的催化剂，并且可以将其重新用于随后的运行中而没有任何明显的活性损失。包括反应中间体的13 C NMR分析和同位素实验在内的机理研究首次证实，这种类型的反应是通过乙烯基阳离子中间体进行的。
• Novel Pd(II)- and Pt(II)-Catalyzed Regio- and Stereoselective <i>trans</i>-Hydroarylation of Alkynes by Simple Arenes
  作者：Chengguo Jia、Wenjun Lu、Juzo Oyamada、Tsugio Kitamura、Kenji Matsuda、Masahiro Irie、Yuzo Fujiwara

  DOI：10.1021/ja0005845

  日期：2000.8.1

  Efficient trans-hydroarylation of alkynes by simple arenes has been realized regio- and stereoselectively at room temperature in the presence of Pd(II) or Pt(II) catalysts and a mixed solvent containing trifluoroacetic acid (TFA). Various arenes undergo trans-hydroarylation selectively across terminal and internal C-C triple bonds-including those conjugated to CHO, COMe, CO2H, and CO2Et groups, affording kinetically controlled cis-arylalkenes predominantly in most cases, especially, in good yields for electron-rich arenes and activated alkynes. The formation of arene/alkyne 1/2 or 2/1 adducts as side products is dependent on the arenes' and alkynes' substituents, which can be suppressed in some cases by changing the catalyst, catalyst concentration, and reaction time. The Pt(II) system, PtCl2/2AgOAc/TFA, shows lower catalytic activity than Pd(OAc)(2)/TFA, but higher selectivity, giving higher yields of adducts at the same conversion. On the basis of several isotope experiments and control reactions, a possible mechanism involving electrophilic metalation of aromatic C-H bonds by in-situ-generated cationic Pd(II) and Pt(II) species leading to intermolecular trans-arylpalladation to alkynes has been discussed.
• A Y-Shaped Tris-<i>N</i>-Heterocyclic Carbene for the Synthesis of Simultaneously Chelate-Monodentate Dipalladium Complexes
  作者：Sergio Gonell、Macarena Poyatos、José A. Mata、Eduardo Peris

  DOI：10.1021/om200820s

  日期：2011.11.14

  A Y-shaped tris-NHC ligand has been obtained and coordinated to palladium, affording metal complexes with novel topological properties. The tris-NHC ligand is capable of coordinating the two metals, affording two different coordination environments. The X-ray molecular structure of two of the complexes are reported. The three new Pd complexes provide good activity in the hydroarylation of alkynes, although we did not find any clear evidence about the benefits of using the dimetallic palladium species in the catalytic outcomes.