(Z)-(1-bromo-2-chloropenta-1,4-dien-1-yl)benzene | 1273588-37-6

• 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: (Z)-(1-bromo-2-chloropenta-1,4-dien-1-yl)benzene
• 英文别名: [(1Z)-1-bromo-2-chloropenta-1,4-dienyl]benzene
• CAS: 1273588-37-6
• 化学式: C₁₁H₁₀BrCl
• 分子量: 257.557
• InChiKey: TTXPXZRDALHHPD-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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-氯乙炔基苯 、 烯丙醇 在 1-羧甲基-3-甲基咪唑溴盐 、 氢溴酸 、 palladium dichloride 作用下， 反应 24.0h， 以81%的产率得到(Z)-(1-bromo-2-chloropenta-1,4-dien-1-yl)benzene
  参考文献：
  名称：

  Synthesis of 1,4-dienes by Pd(II)-catalyzed haloallylation of alkynes with allylic alcohols in ionic liquids

  摘要：

  A Pd-catalyzed haloallylation of alkynes with ally] alcohols in ionic liquids has been reported. Both chloroallylation and bromoallylation can be easily carried out with high selectivity. A variety of 1,4-dienes were formed in moderate to excellent yields. The reaction system of the Pd catalyst as well as the ionic liquid can be recycled for several times. And the ionic liquid acts as not only a solvent in the reaction, but also provides the excess halide ions to control Z/E selectivity and acts as a ligand inhibit the beta-hydride elimination. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.10.100

文献信息

• Palladium-catalyzed highly regio- and stereoselective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes via haloallylation of alkynyl halides
  作者：Xiaoyi Chen、Wei Kong、Haiting Cai、Lichun Kong、Gangguo Zhu

  DOI：10.1039/c0cc04879h

  日期：——

  A highly efficient and selective synthesis of (1E)- or (1Z)-1,2-dihalo-1,4-dienes viaPd-catalyzed coupling of haloalkynes and allylic halides is described. The (1E)-1,2-dihalo-1,4-dienes were generated in good yields with excellent stereoselectivities (1E/1Z up to >98/2), while (1Z)-1,2-dihalo-1,4-dienes were produced in excellent yields and stereoselectivities (1Z/1E up to >98/2) by simply adding stoichiometric lithium halides.

  描述了一种高效且选择性强的合成(1E)-或(1Z)-1,2-二卤-1,4-二烯的方法，该方法通过钯催化的卤代炔与烯丙卤化物的偶联反应实现。(1E)-1,2-二卤-1,4-二烯以良好的产率和优异的立体选择性生成（1E/1Z高达>98/2），而(1Z)-1,2-二卤-1,4-二烯则通过简单添加当量的锂卤化物以优秀的产率和立体选择性生成（1Z/1E高达>98/2）。
• Synthesis of 1,4-dienes by Pd(II)-catalyzed haloallylation of alkynes with allylic alcohols in ionic liquids
  作者：Jianxiao Li、Shaorong Yang、Wanqing Wu、Chaorong Qi、Zhongxian Deng、Huanfeng Jiang

  DOI：10.1016/j.tet.2013.10.100

  日期：2014.2

  A Pd-catalyzed haloallylation of alkynes with ally] alcohols in ionic liquids has been reported. Both chloroallylation and bromoallylation can be easily carried out with high selectivity. A variety of 1,4-dienes were formed in moderate to excellent yields. The reaction system of the Pd catalyst as well as the ionic liquid can be recycled for several times. And the ionic liquid acts as not only a solvent in the reaction, but also provides the excess halide ions to control Z/E selectivity and acts as a ligand inhibit the beta-hydride elimination. (C) 2014 Published by Elsevier Ltd.