(E)-cinnamyl 4-methylphenylpropiolate | 1253101-18-6

• 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: (E)-cinnamyl 4-methylphenylpropiolate
• 英文别名: [(E)-3-phenylprop-2-enyl] 3-(4-methylphenyl)prop-2-ynoate
• CAS: 1253101-18-6
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: GYENUWFFYDLCTO-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二氧化碳 、 肉桂基氯 、 4-甲苯基乙炔 在 caesium carbonate 、 silver(I) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 60.0 ℃ 、1.5 MPa 条件下， 反应 24.0h， 以91%的产率得到(E)-cinnamyl 4-methylphenylpropiolate
  参考文献：
  名称：

  Ligand-free Ag(I)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO2

  摘要：

  Simple silver(I) slats were found to be highly efficient and selective catalyst for carboxylative coupling of aryl- or alkyl-substituted terminal alkynes, CO2, and various allylic, propargylic or benzylic chlorides to exclusively yield functionalized 2-alkynoates. The activity is about 300 times that of the previously reported N-heterocyclic carbene copper(I) catalytic system. The ligand-free silver(I) catalytic system showed the wide generality of substrates involving both functionalized terminal alkynes and chloride compounds. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.053

文献信息

• Cu(I)-Catalyzed Carboxylative Coupling of Terminal Alkynes, Allylic Chlorides, and CO₂
  作者：Wen-Zhen Zhang、Wen-Jie Li、Xiao Zhang、Hui Zhou、Xiao-Bing Lu

  DOI：10.1021/ol102172v

  日期：2010.11.5

  A highly selective synthesis of a variety of functionalized allylic 2-alkynoates was realized via the carboxylative coupling of terminal alkynes, allylic chlorides, and CO2 catalyzed by the N-heterocyclic carbene copper(I) complex (IPr)CuCl. The catalyst can be easily recovered without any loss in activity and product selectivity.

  通过N-杂环卡宾铜（I）配合物（IPr）CuCl催化的末端炔烃，烯丙基氯化物和CO 2的羧基偶联，实现了多种官能化烯丙基2-链烷酸酯的高度选择性合成。可以容易地回收催化剂，而没有任何活性和产物选择性的损失。
• Ligand-free Ag(I)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO2
  作者：Xiao Zhang、Wen-Zhen Zhang、Ling-Long Shi、Chuang Zhu、Jiao-Lai Jiang、Xiao-Bing Lu

  DOI：10.1016/j.tet.2012.08.053

  日期：2012.11

  Simple silver(I) slats were found to be highly efficient and selective catalyst for carboxylative coupling of aryl- or alkyl-substituted terminal alkynes, CO2, and various allylic, propargylic or benzylic chlorides to exclusively yield functionalized 2-alkynoates. The activity is about 300 times that of the previously reported N-heterocyclic carbene copper(I) catalytic system. The ligand-free silver(I) catalytic system showed the wide generality of substrates involving both functionalized terminal alkynes and chloride compounds. (C) 2012 Elsevier Ltd. All rights reserved.