(Z)-2-(chloro(phenyl)methylene)pent-4-enamide | 1392486-29-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-(chloro(phenyl)methylene)pent-4-enamide
• 英文别名: (2Z)-2-[chloro(phenyl)methylidene]pent-4-enamide
• CAS: 1392486-29-1
• 化学式: C₁₂H₁₂ClNO
• 分子量: 221.686
• InChiKey: XGPNWQCWQQXLKT-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-苯基丙-2-炔酰胺 、 烯丙醇 在 1-羧甲基-3-甲基咪唑氯盐 、 palladium dichloride 作用下， 以 水 为溶剂， 反应 24.0h， 以61%的产率得到(Z)-2-(chloro(phenyl)methylene)pent-4-enamide
  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

• Switch of Selectivity in the Synthesis of α-Methylene-γ-Lactones: Palladium-Catalyzed Intermolecular Carboesterification of Alkenes with Alkynes
  作者：Liangbin Huang、Qian Wang、Xiaohang Liu、Huanfeng Jiang

  DOI：10.1002/anie.201109141

  日期：2012.6.4

  Three in one: A highly efficient and mild PdII‐catalyzed carboesterification of alkenes with carboxylic alkyne derivatives proceeds through a domino‐type alkyne–alkene coupling/CO‐bond formation (see scheme). The stereoselectivity is controlled by the choice of substrates and temperature. The reaction provides a convenient method for the construction of naturally occurring biologically active compounds

  三合一：高效，温和的Pd II催化的烯烃与羧基炔烃衍生物的碳酯化反应通过多米诺型炔烃-烯烃偶联/ CO键形成（参见方案）进行。立体选择性是通过选择底物和温度来控制的。该反应为构建具有α-亚甲基-γ-内酯骨架的天然生物活性化合物提供了便利的方法。
• 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.