(E)-(1,2-dibromobut-1-en-1-yl)benzene | 69298-48-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(1,2-dibromobut-1-en-1-yl)benzene
• 英文别名: [(E)-1,2-dibromobut-1-enyl]benzene
• CAS: 69298-48-2
• 化学式: C₁₀H₁₀Br₂
• 分子量: 289.997
• InChiKey: LRVBRQHJYCSYST-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  1-苯基-1-丁炔 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 lithium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以61%的产率得到(E)-(1,2-dibromobut-1-en-1-yl)benzene
  参考文献：
  名称：

  使用原位生成的ICl，IBr，BrCl，I2和Br2进行1，2-二卤代烯烃的区域和立体选择性合成。

  摘要：

  我们描述了炔烃的无催化剂的1,2-反式二卤代反应，具有空前的底物范围和排他性和立体选择性。这种多功能的二卤化系统-NX 1 S亲电试剂和乙酸中的碱金属卤化物（MX 2）的组合-适用于各种类型的炔烃（富电子或弱炔烃，内部和末端炔烃，或杂原子，例如O- ，N-，S-取代的炔烃）。氢键供体溶剂乙酸对于就地生成X 1 X 2亲电试剂（包括ICl，IBr，BrCl，I 2和Br 2）是必不可少的。

  DOI：

  10.1016/j.chempr.2020.03.011

文献信息

• Stereoselective Halogenations of Alkenes and Alkynes in Ionic Liquids
  作者：Cinzia Chiappe、Dario Capraro、Valeria Conte、Daniela Pieraccini

  DOI：10.1021/ol015631s

  日期：2001.4.1

  [GRAPHICS]Room-temperature ionic liquids, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium bromide, and 1-butyl-3-methylimidazolium chloride, are used as "green" recyclable alternative to chlorinated solvents for the stereoselective halogenation of alkenes and alkynes.
• Selective 1,2-dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides
  作者：Jinhua Liu、Wenjuan Li、Chao Wang、Yao Li、Zhiping Li

  DOI：10.1016/j.tetlet.2011.06.047

  日期：2011.8

  1,2-Dihalogenation and oxy-1,1-dihalogenation of alkynes by N-halosuccinimides can be selectively realized through using different reaction conditions. alpha,beta-Dihalo alkenes were obtained exclusively using THF as solvent without using any catalyst, while alpha,alpha-dihalo ketones were synthesized using a mixed solvent of THF and H2O in the presence of FeCl3 center dot 6H(2)O. Terminal aromatic alkynes are smoothly transformed into alpha,alpha-dihalo ketones on water without a catalyst. (C) 2011 Elsevier Ltd. All rights reserved.
• 10.1002/1099-0690(200208)2002:16<2831::aid-ejoc2831<3.0.co;2-t
  作者：Chiappe, Cinzia、Conte, Valeria、Pieraccini, Daniela

  DOI：10.1002/1099-0690(200208)2002:16<2831::aid-ejoc2831<3.0.co;2-t

  日期：——
• Spectroscopic and Theoretical Investigations of Electrophilic Bromination Reactions of Alkynes: The First Evidence for π Complexes as Reaction Intermediates
  作者：Roberto Bianchini、Cinzia Chiappe、Giacomo Lo Moro、Dieter Lenoir、Peter Lemmen、Norman Goldberg

  DOI：10.1002/(sici)1521-3765(19990503)5:5<1570::aid-chem1570>3.0.co;2-a

  日期：1999.5.3

  A bromine-alkyne pi complex (lambda(max) = 294 nm) of 1:1 stoichiometry has been observed for the first time in the course of the bromination of 1-phenylpropyne by means of a diode-array stopped-flow technique. The formation enthalpy and entropy (Delta H?= -2.95 kcalmol(-1), Delta S-25?=-15.4eu) of this species are similar to those of charge-transfer complexes observed between bromine and alkenes. A negative apparent activation energy is found in the reaction of Br, with 1-phenylpropyne (Delta H-not equal=-0.61 kcalmol(-1)); this demonstrates that the complex is actually an essential intermediate on the reaction coordinate. The bromination of a series of nine alkynes has been studied. Bromination reactions with negative apparent activation parameters lead to mixtures of E and Z vinyl dibromides, whereas reactions with positive activation energy yield the E isomers exclusively. The reason for the difference in reactivity of these alkynes compared with structurally similar alkenes most likely lies in the stability of these 1:1 charge-transfer complexes. Usually open arylvinyl cations correspond to the energetically favored product-determining intermediates; bridged bromirenium ions are formed from deactivated alkynes and react to give E isomers. The kinetic effect of alkyl groups and of p-OCH3, p-CN, and p-NO2 substituents at the aryl group on the bromination of arylalkylacetylenes is discussed. Density functional calculations provide insight into the geometries, energies, and bonding of the intermediate 1:1 and 2:1 Br-2-acetylene complexes involved. These theoretical investigations demonstrate that the most stable trimolecular Br-2-Br-2-acetylene adduct possesses a structure very similar to a crystallographically characterized Br-2-Br-2-alkene species, which can directly yield the ionic products, Br-3(-) and vinyl cation, driven by the heterolytic action of a solvent.
• Method for Transforming Alkynes into (<i>E</i>)-Dibromoalkenes
  作者：Jiannan Xiang、Rui Yuan、Ruijia Wang、Niannian Yi、Linghui Lu、Huaxu Zou、Weimin He

  DOI：10.1021/jo501776b

  日期：2014.12.5

  The highly stereoselective bromination of alkynes has been realized by using copper(II) bromide as both the reacting partner and the catalyst, offering a generally efficient synthesis of (E)-dibromoalkenes. The reaction conditions are exceptionally mild, and a wide range of functional groups are well tolerated.