3-(4-甲苯基)环戊烯 | 2362-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-甲苯基)环戊烯
• 英文名称: 3-(p-tolyl)cyclopentene
• 英文别名: 3-tolylcyclopentene；3-(p-Methyl-phenyl)-cyclopenten；1-Cyclopent-2-en-1-yl-4-methylbenzene
• CAS: 2362-70-1
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: SXFBCOHDHUTHEC-UHFFFAOYSA-N

物化性质

• 沸点：
  71 °C(Press: 2 Torr)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902909090

反应信息

• 作为产物：
  描述：

  (E)-1-(2-cyclopropylvinyl)-4-methylbenzene 在 bis(1,5-cyclooctadiene)nickel (0) 、 二茂铁 、 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 氘代苯 为溶剂， 生成 3-(4-甲苯基)环戊烯
  参考文献：
  名称：

  Mechanism of the Ni(0)-Catalyzed Vinylcyclopropane−Cyclopentene Rearrangement

  摘要：

  A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclo-propane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

  DOI：

  10.1021/jo901525u

文献信息

• Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions
  作者：Emma Artuso、Margherita Barbero、Iacopo Degani、Stefano Dughera、Rita Fochi

  DOI：10.1016/j.tet.2006.01.027

  日期：2006.3

  Arenediazonium o-benzenedisulfonimides can be used as new and efficient reagents for Heck-type arylation reactions of some common substrates containing C–C multiple bonds, namely ethyl acrylate, acrylic acid, acroleyne, styrene and cyclopentene. The reactions were carried out in an organic solvent, in the presence of Pd(OAc)2 as pre-catalyst, and gave rise to arylated products, for example, ethyl cinnamates

  Arenediazonzon邻苯二磺酰亚胺可用作一些常见的含C-C多键底物，即丙烯酸乙酯，丙烯酸，丙烯醛，苯乙烯和环戊烯的Heck型芳基化反应的新型高效试剂。反应在有机溶剂中，在作为前催化剂的Pd（OAc）2存在下进行，并产生芳基化产物，例如肉桂酸乙酯，肉桂酸，肉桂醛和对苯二甲酸酯，具有（E） -构型和1-芳基环戊烯，收率良好至优异。值得注意的是，所有反应导致以大于80％的产率回收邻苯二磺酰亚胺，该邻苯二磺酰亚胺可再循环用于制备其他重氮盐。
• An Efficient Procedure for the Synthesis of Crystalline Aryldiazonium Trifluoroacetates – Synthetic Applications
  作者：Christophe Colas、Maurice Goeldner

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1357::aid-ejoc1357>3.0.co;2-p

  日期：1999.6

  spectra have been recorded for all the synthesized salts; the data are in good agreement with the rather limited published data and constitute a first extensive report of 13C-NMR chemical shifts in diazonium salts. An excellent linear relationship emerged between Brown's substituent constants s+p and the 13Cipso chemical shifts. The diazonium salts obtained proved to be much more soluble in organic

  我们开发了一种非常温和的方法，用于在无水条件下以高产率合成结晶芳基重氮三氟乙酸盐。超过 30 种单官能或多官能苯胺衍生物已通过这种方法重氮化，包括对水和酸敏感的底物。衍生自相应苯胺的邻和对羟基芳基重氮盐可以通过用 K2CO3 处理去质子化以产生纯的重氮醌。已记录所有合成盐的 NMR 和 UV/Vis 光谱；这些数据与相当有限的公开数据非常吻合，并构成了重氮盐中 13C-NMR 化学位移的第一份广泛报告。Brown 的取代基常数 s+p 和 13Cipso 化学位移之间出现了极好的线性关系。获得的重氮盐证明比它们的四氟硼酸盐对应物更易溶于有机溶剂。它们在各种碳-碳双键的 Pd 介导的偶联反应中进行了测试，发现在非常温和的条件下，在很短的反应时间内获得了良好的产率。我们相信重氮三氟乙酸盐是重氮四氟硼酸盐的一种非常有吸引力的替代品。
• Reaction of diazonium salts with transition metals—III
  作者：K. Kikukawa、K. Nagira、F. Wada、T. Matsuda

  DOI：10.1016/s0040-4020(01)97711-7

  日期：1981.1

  Palladium (0) catalyzed reactions of arenediazonium salts for arylation of aliphatic and cyclic olefins and allylic alcohols, styrene and ethyl acrylate were studied. Effects of the olefinic compounds and other reaction variables on the arylation were presented. Arylpalladium species was proposed as the most plausible intermediated in this reaction.

  研究了钯（0）催化烯丙基二氮杂鎓盐使脂族和环状烯烃与烯丙基醇，苯乙烯和丙烯酸乙酯芳基化的反应。提出了烯烃化合物和其他反应变量对芳基化的影响。有人提出，芳钯是该反应中最合理的中间体。
• Hybrid Birch-Claisen Methodology for arylation at allylic termini: synthesis of (±)-herbertene
  作者：S. Chandrasekaran、John V. Turner

  DOI：10.1016/s0040-4039(00)87711-4

  日期：1982.1

  A hybrid Birch-Claisen methodology has been developed for the regio- and stereo-controlled arylation of allyl groups, and applied to a synthesis of (±)-herbertene.

  已开发出一种混合的Birch-Claisen方法，用于烯丙基的区域和立体控制的芳基化，并用于合成（±）-香柏烯。
• Arylation of Olefins by Arylazo Aryl Sulfones under Palladium(0) Catalysis
  作者：Nobumasa Kamigata、Akira Satoh、Tetsuya Kondoh、Masayuki Kameyama

  DOI：10.1246/bcsj.61.3575

  日期：1988.10

  The palladium(0)-catalyzed reaction of arylazo aryl sulfones with olefins in benzene at 80°C gave aryl-substituted olefins in good yield. Diarylpalladium(II) species was proposed as an intermediate in this reaction.

  在 80°C 下，芳基偶氮芳基砜与烯烃在苯中的钯 (0) 催化反应以良好的收率得到芳基取代的烯烃。二芳基钯 (II) 物种被提议作为该反应的中间体。