(E)-2,2'-(but-1-ene-1,3-diyl)bis(methylbenzene) | 35192-31-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-2,2'-(but-1-ene-1,3-diyl)bis(methylbenzene)
• 英文别名: 1,3-di(2-methylphenyl)butene；1,3-Ditolyl-1-butene；1-methyl-2-[(E)-3-(2-methylphenyl)but-1-enyl]benzene
• CAS: 35192-31-5
• 化学式: C₁₈H₂₀
• 分子量: 236.357
• InChiKey: NJDWYMKXLVDPTB-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-甲基苯乙烯 在 双三氟甲烷磺酰亚胺 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 12.0h， 以82%的产率得到(E)-2,2'-(but-1-ene-1,3-diyl)bis(methylbenzene)
  参考文献：
  名称：

  Efficient hydroarylation and hydroalkenylation of vinylarenes by Brønsted acid catalysis

  摘要：

  Brønsted酸Tf₂NH催化的4个乙烯芳烃的水合芳基化和水合烯基化反应在温和的反应条件下显示出高产率和优异的区域选择性，可获得1,1-二芳基烷骨架和反-1,3-二芳基-1-丁烯。

  DOI：

  10.1039/c6ra16627j

文献信息

• Dehydrative Coupling of Benzylic Alcohols Catalyzed by Brønsted Acid/Lewis Base
  作者：Marlene Böldl、Ivana Fleischer

  DOI：10.1002/ejoc.201900965

  日期：2019.9.15

  A combination of Brønsted acid and Lewis base catalyses two dehydrative transformations of benzylic alcohols: homocoupling and hydroarylation.

  布朗斯台德酸和路易斯碱的组合催化苄醇的两个脱水转化：均偶联和氢芳基化。
• Highly efficient TfOH-catalyzed head-to-tail dimerization of vinylarenes
  作者：Hui-Lan Yue、Xiao-Hui Zhao、Lei Jiang、Yun Shao、Li-Juan Mei

  DOI：10.1080/00397911.2015.1127384

  日期：2016.1.17

  ABSTRACT A convenient and efficient TfOH-catalyzed head-to-tail dimerization of vinylarenes has been realized under mild conditions. The present protocol provides an attractive approach to a diverse range of higher olefins in good to excellent yields. GRAPHICAL ABSTRACT

  摘要 在温和的条件下实现了一种方便、高效的 TfOH 催化的乙烯基芳烃头对尾二聚反应。本协议为各种高级烯烃提供了一种有吸引力的方法, 具有良好的收率。图形概要
• Iron-Catalysed Regio- and Stereoselective Head-to-Tail Dimerisation of Styrenes
  作者：Jose R. Cabrero-Antonino、Antonio Leyva-Pérez、Avelino Corma

  DOI：10.1002/adsc.201000096

  日期：——

  Cationic iron salts and complexes catalyse the head‐to‐tail dimerisation of styrene derivatives to form the corresponding dimers with good to excellent yields and stereoselectivities. In particular, the use of a phosphine‐iron(III) complex allows the recovery and reuse of the catalyst. The counteranion plays an important role in both the activity and selectivity. These catalysts constitute an alternative

  阳离子铁盐和络合物催化苯乙烯衍生物从头到尾的二聚反应，形成相应的二聚体，具有良好或优异的收率和立体选择性。特别是，使用膦-铁（III）配合物可以回收和再利用催化剂。抗衡阴离子在活性和选择性中都起着重要作用。这些催化剂构成了基于有毒且昂贵的后期过渡金属的催化剂的替代品。
• Highly efficient Pd(acac)2/TFA catalyzed head-to-tail dimerization of vinylarenes at room temperature
  作者：Hengchang Ma、Qiangsheng Sun、Wenfeng Li、Jinxia Wang、Zhe Zhang、Yaoxia Yang、Ziqiang Lei

  DOI：10.1016/j.tetlet.2011.01.056

  日期：2011.4

  Pd(acac)2 catalyzed dimerization of vinylarenes to form dimers under mild condition with excellent yields and stereoselectivities. In particular, the use of TFA highly promoted the activity and selectivity of the dimerization. The studies on mechanism for the reaction displayed clearly that the dimerization of styrenes is 100% atom economic reaction.

  Pd（acac）2在温和条件下以极佳的收率和立体选择性催化乙烯基芳烃的二聚反应，形成二聚体。特别地，使用TFA极大地促进了二聚作用的活性和选择性。对反应机理的研究清楚地表明，苯乙烯的二聚是100％原子经济反应。
• Iron-Catalyzed Stereospecific Olefin Synthesis by Direct Coupling of Alcohols and Alkenes with Alcohols
  作者：Zhong-Quan Liu、Yuexia Zhang、Lixing Zhao、Zejiang Li、Jiantao Wang、Huajie Li、Long-Min Wu

  DOI：10.1021/ol200372y

  日期：2011.5.6

  An efficient Fe(III)-catalyzed direct coupling of alkenes with alcohols and cross-coupling of alcohols with alcohols to give the corresponding substituted (E)-alkenes stereospecifically is demonstrated. Additionally, this reaction could be scaled up. The kinetic isotope effect (KIE) experiments indicated a typical secondary isotope effect in this process. Although benzylic alcohols were effective substrates, mild conditions, atom efficiency, environmental soundness, and stereospecificity are features that make this procedure very attractive.