1-ethyl-2-styrylbenzene

• 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: 1-ethyl-2-styrylbenzene
• 英文别名: Ethylstilbene；1-ethyl-2-(2-phenylethenyl)benzene
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: GEUYACYJMUQXCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 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：

  在 三乙基硅烷 、 三(五氟苯基)硼烷 作用下， 以 氘代氯仿 为溶剂， 反应 4.0h， 以87%的产率得到1-ethyl-2-styrylbenzene
  参考文献：
  名称：

  B（C 6 F 5）3-使用氢硅烷催化加氢脱硫–硫化物的无金属还原

  摘要：

  使用三乙基硅烷作为还原剂，实现了B（C 6 F 5）3催化的碳硫键加氢脱硫。在温和的反应条件下以高收率获得了相应的产物。该方案可用于具有高化学选择性的硫化物的还原，包括苄基和烷基硫化物以及二噻烷。

  DOI：

  10.1021/acs.orglett.5b01651

文献信息

• Synthesis of Highly Substituted Arenes via Cyclohexadiene–Alkene C–H Cross Coupling and Aromatization
  作者：Anup Bhunia、Armido Studer

  DOI：10.1021/acscatal.8b00083

  日期：2018.2.2

  The development of a cross-coupling method for the regioselective β-alkenylation of 2,5-cyclohexadiene carboxylic acid derivatives to form ortho-alkenylarenes through in situ decarboxylation and aromatization is described. The carboxylic acid functionality is used as a traceless directing group for efficient and mild β-alkenylation. The modular sequence comprises a reductive Birch α-alkylation, ionic

  描述了交叉偶联方法的发展，该交叉偶联方法用于2，5-环己二烯羧酸衍生物的区域选择性β-烯基化以通过原位脱羧和芳构化形成邻烯基芳烃。羧酸官能团用作有效且温和的β-烯基化反应的无痕导向基团。模块化序列包括还原桦木α烷基化，离子δ烷基化，接着通过Pd催化的脱羧β烯基化，随后芳构化导致整体三倍本位-对位-邻位容易访问的苯甲酸衍生物的官能化。提出了在温和条件下以中等至极好的收率高效合成各种烷基-烯基芳烃的方法。
• Iron catalysis for the synthesis of ligands: Exploring the products of hydrophosphination as ligands in cross-coupling
  作者：Maialen Espinal-Viguri、Mary F. Mahon、Simon N.G. Tyler、Ruth L. Webster

  DOI：10.1016/j.tet.2016.11.058

  日期：2017.1

  Catalytic hydrophosphination is a useful technique for the synthesis of phosphines, however, the phosphine products have been little exploited as ligands in catalysis. We have selected three phosphines prepared by iron catalyzed hydrophosphination and used them as ligands in a series of cross-coupling reactions: Heck, Suzuki-Miyaura and Buchwald-Hartwig. Rather than limit the chemistry to simple cross-coupling

  催化氢磷酸化是合成膦的有用技术，但是，膦产物几乎没有被用作催化中的配体。我们选择了铁催化氢磷酸化制备的三种膦，并将它们用作一系列交叉偶联反应的配体：Heck，Suzuki-Miyaura和Buchwald-Hartwig。与其将化学反应局限于几乎可以保证在这些转化中表现良好的简单交叉偶联配偶体，还探索了从电子和/或立体角度来看具有挑战性的工业相关底物，以及包含多个杂原子的底物，以实现以下目的：测量这些膦配体的真正潜力。
• Synthesis and catalytic activity of pyrazolyl-functionalized N-heterocyclic carbene palladium complexes
  作者：Cai-Hong Cheng、Jia-Ru Xu、Hai-Bin Song、Liang-Fu Tang

  DOI：10.1007/s11243-013-9784-7

  日期：2014.3

  Three pyrazolyl-functionalized N-heterocyclic carbene (NHC) palladium complexes based on 1-[2-(pyrazol-1-yl)phenyl]imidazole have been synthesized and characterized by physico-chemical and spectroscopic methods, and the structures of two of the complexes have been confirmed by single-crystal X-ray diffraction. The pyrazolyl-functionalized NHCs act as chelating N,C-bidentate ligands in these three complexes. Catalytic tests have proved that these complexes exhibit highly effective catalytic activity for the Suzuki–Miyaura and Mizoroki–Heck coupling reactions in water or aqueous/organic media under air. The substituents on the pyrazolyl ring exert different influences on the catalytic activity of the complexes in these coupling reactions.

  基于1-[2-(吡唑-1-基)苯基]咪唑的三种吡唑功能化的N-杂环卡宾(NHC)钯配合物已通过物理化学和光谱方法合成并表征，其中两种配合物的结构经单晶X射线衍射确认。吡唑功能化的NHC在这些配合物中充当螯合的N,C-双齿配体。催化测试证明，这些配合物在空气下水中或水/有机溶剂中对铃木-宫浦和沟吕木- Heck偶联反应表现出极高的催化活性。吡唑环上的取代基对这些偶联反应中配合物的催化活性产生不同影响。
• Rhodium-catalysed anomalous dimerization of styrenes involving the cleavage of the ortho C–H bond
  作者：Mamoru Tobisu、Isao Hyodo、Masahiro Onoe、Naoto Chatani

  DOI：10.1039/b806285d

  日期：——

  The dimerization of styrene derivatives in the presence of a rhodium catalyst proceeds to give stilbene derivatives, in which the ortho C-H bond of styrenes is cleaved and functionalized.

  在铑催化剂的存在下，苯乙烯衍生物的二聚化得到二苯乙烯衍生物，其中苯乙烯的邻位CH键被裂解并官能化。
• A Robust First-Pass Protocol for the Heck–Mizoroki Reaction
  作者：Paul M. Murray、John F. Bower、David K. Cox、Ewan K. Galbraith、Jeremy S. Parker、Joseph B. Sweeney

  DOI：10.1021/op300364p

  日期：2013.3.15

  The Heck-Mizoroki (HM) reaction is one of the most widely used C-C bond-forming methods of contemporary synthesis. Notwithstanding this, these reactions frequently require significant optimization before efficient transformations can be obtained. We describe here the results of a study that aimed to establish a generic experimental protocol for HM reactions which enables acceptable yields from first-pass experiments. The methodology utilizes readily available stable catalysts and can be applied to a broad range of coupling partners.