(E)-2,2'-(but-1-ene-1,3-diyl)bis(chlorobenzene)

• 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(chlorobenzene)
• 英文别名: 1-chloro-2-[(E)-3-(2-chlorophenyl)but-1-enyl]benzene
• 化学式: C₁₆H₁₄Cl₂
• 分子量: 277.193
• InChiKey: YMMKVUSWOILJIP-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-(2-氯苯基)乙醇 在 对甲苯磺酸 、 三苯基膦 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以27%的产率得到(E)-2,2'-(but-1-ene-1,3-diyl)bis(chlorobenzene)
  参考文献：
  名称：

  布朗斯台德酸/路易斯碱催化的苄醇的脱水偶联

  摘要：

  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。

  DOI：

  10.1002/ejoc.201900965

文献信息

• 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
• Investigation of the behavior of arenediazonium salts with olefins in BmimPF6
  作者：George W. Kabalka、Gang Dong、Bollu Venkataiah

  DOI：10.1016/j.tetlet.2004.02.023

  日期：2004.3

  The palladium-catalyzed reactions of olefins with arenediazonium salts in ionic liquids were investigated. For methyl acrylate and methyl acrylonitrile, normal Heck cross-coupling products are obtained in good yields. However, highly selective dimerization products are formed in excellent yields for styrenes. The catalyst system can be recycled.

  研究了钯在离子液体中钯与烯烃的催化反应。对于丙烯酸甲酯和甲基丙烯腈，可以以良好的产率获得普通的Heck交叉偶联产物。然而，对于苯乙烯而言，形成高选择性二聚产物以优异的产率形成。催化剂体系可以循环使用。
• Iodine-Promoted Metal-Free Head-to-Tail Dimerization of Styrenes Affording 1,3-Diarylbut-1-enes
  作者：Sen Lin、Shengmei Guo、Dingyi Wang、Yanjiao Fang、Qihuang Xie、Zhaohua Yan

  DOI：10.1055/s-0036-1589214

  日期：——

  A convenient and efficient iodine-mediated head-to-tail dimerization of styrenes to produce the corresponding dimers in the presence of triethyl phosphite is reported. The advantages of the present protocol are metal-free conditions, short reaction time, simplicity, and high efficiency.

  据报道，在亚磷酸三乙酯存在下，一种方便且有效的碘介导的苯乙烯头对尾二聚反应产生相应的二聚体。本协议的优点是无金属条件、反应时间短、简单、效率高。
• Metal-Free and Recyclable Route to Synthesize Polysubstituted Olefins<i>via</i>CC Bond Construction from Direct Dehydrative Coupling of Alcohols or Alkenes with Alcohols Catalyzed by Sulfonic Acid-Functionalized Ionic Liquids
  作者：Feng Han、Lei Yang、Zhen Li、Yingwei Zhao、Chungu Xia

  DOI：10.1002/adsc.201301150

  日期：2014.8.11

  AbstractA direct synthesis of polysubstituted olefins via construction of CC bonds, which involves the direct dehydrative coupling of alcohols or alkenes with alcohols, was realized using a series of alkanesulfonic acid group‐functionalized ionic liquids (SO3H‐functionlization ILs) without additives. The metal‐free and recyclable catalyst system avoided the disposal and neutralization of acidic catalysts after reaction and tolerated a broad range of substrates, including benzylic, allyl, propargylic, aliphatic and aromatic or aliphatic olefins. Additionally, the catalytic system was suitable for a gram‐scale preparation. Preliminary mechanistic studies indicated that the CH bond cleavage in this reaction might be involved in the rate‐determining step.magnified image
• 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.