ethyl 6-phenylhex-5-yn-3(E)-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 6-phenylhex-5-yn-3(E)-enoate
• 英文别名: ethyl (E)-6-phenylhex-3-en-5-ynoate
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: VWXLCKZALMFMQK-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  顺-3-溴丙烯酸乙酯 在 正丁基锂 、 mercury dichloride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.67h， 生成 ethyl 6-phenylhex-5-yn-3(E)-enoate
  参考文献：
  名称：

  Unusual Regioselectivity of Pd(0)-Catalyzed Coupling Reaction of Electron-Deficient Alkenyl Halides with Allenic/Propargylic Zinc Reagents. Highly Selective Synthesis of 6-Phenylhex-5-yn-2(or 3)-enoates/Enitrile and 4-Phenyl-6-substituted-hexa-2,4,5-trienoates

  摘要：

  The Pd(0)-catalyzed coupling reaction of electron-deficient alkenyl halides with the organozinc formed by the subsequent treatment of 1-phenylalk-1-yne with n-BuLi and ZnBr2 with or without a catalytic amount of HgCl2 was studied. Both the allene-formation- and the alkyne-formation-type coupling reactions were observed with high regio- and stereoselectivity: the reaction of 1-phenylprop-1-yne afforded 6-phenylhex-5-yn-2(or 3)-enoates and -enitriles, while the reaction of 1-phenylhex-1-yne formed 4-phenyl-6-substituted-hexa-2,4,5-trienoates. A plausible explanation for the regioselectivity was discussed. The double bonds in 6-phenylhex-5-yn-2-enoates were prone to migrate to the position conjugated with the carbon-carbon triple bonds to form 6-phenylhex-5-yn-3-enoates at higher temperature. The migration did not occur in absence of an excess amount of allenic/propargylic zinc reagent or at low temperature.

  DOI：

  10.1021/jo991243g

文献信息

• Unusual Regioselectivity of Pd(0)-Catalyzed Coupling Reaction of Electron-Deficient Alkenyl Halides with Allenic/Propargylic Zinc Reagents. Highly Selective Synthesis of 6-Phenylhex-5-yn-2(or 3)-enoates/Enitrile and 4-Phenyl-6-substituted-hexa-2,4,5-trienoates
  作者：Shengming Ma、Aibin Zhang、Yihua Yu、Wei Xia

  DOI：10.1021/jo991243g

  日期：2000.4.1

  The Pd(0)-catalyzed coupling reaction of electron-deficient alkenyl halides with the organozinc formed by the subsequent treatment of 1-phenylalk-1-yne with n-BuLi and ZnBr2 with or without a catalytic amount of HgCl2 was studied. Both the allene-formation- and the alkyne-formation-type coupling reactions were observed with high regio- and stereoselectivity: the reaction of 1-phenylprop-1-yne afforded 6-phenylhex-5-yn-2(or 3)-enoates and -enitriles, while the reaction of 1-phenylhex-1-yne formed 4-phenyl-6-substituted-hexa-2,4,5-trienoates. A plausible explanation for the regioselectivity was discussed. The double bonds in 6-phenylhex-5-yn-2-enoates were prone to migrate to the position conjugated with the carbon-carbon triple bonds to form 6-phenylhex-5-yn-3-enoates at higher temperature. The migration did not occur in absence of an excess amount of allenic/propargylic zinc reagent or at low temperature.