methyl 4-phenylnona-2(E),4,5-trienoate

• 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: methyl 4-phenylnona-2(E),4,5-trienoate
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: UQTJASZCIYDEPT-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (Z)-3-碘代丁-2-烯酸甲酯 、 1-苯基-1-己炔 在 正丁基锂 、 zinc dibromide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.57h， 生成 methyl 4-phenylnona-2(E),4,5-trienoate
  参考文献：
  名称：

  配体对3-碘代-2--2-烯酸酯与炔丙基/ 1,2-烯基金属物种在Pd催化下的交叉偶联反应的影响：2,4,5-三烯酸酯的高效区域发散性合成

  摘要：

  配体有很大的不同：炔丙基/ 1,2-烯丙基锂的1,3-锂转移已被调整并应用于随后的金属转移和Pd催化的Negishi与3-碘代烷基-2-烯酸酯的偶联反应，得到2,4,5-三烯酸酯的高度区域选择性和区域发散性合成。已发现，就区域选择性和反应性而言，配体在交叉偶联反应中起着非常重要的作用。

  DOI：

  10.1002/chem.200901287

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.
• Ligand Effects on the Pd-Catalyzed Cross-Coupling Reaction of 3-Iodoalk-2-enoates with Propargyl/1,2-Allenylic Metallic Species: An Efficient Regiodivergent Synthesis of 2,4,5-Trienoates
  作者：Jinbo Zhao、Yihua Yu、Shengming Ma

  DOI：10.1002/chem.200901287

  日期：2010.1.4

  makes a big difference: The 1,3‐lithium shift of propargyl/1,2‐allenyl lithium has been tuned and applied in a subsequent transmetalation and Pd‐catalyzed Negishi coupling reaction with 3‐iodoalk‐2‐enoates to give a highly regioselective and regiodivergent synthesis of 2,4,5‐trienoates. It was discovered that ligands play a very important role in the cross‐coupling reactions with respect to both regioselectivity

  配体有很大的不同：炔丙基/ 1,2-烯丙基锂的1,3-锂转移已被调整并应用于随后的金属转移和Pd催化的Negishi与3-碘代烷基-2-烯酸酯的偶联反应，得到2,4,5-三烯酸酯的高度区域选择性和区域发散性合成。已发现，就区域选择性和反应性而言，配体在交叉偶联反应中起着非常重要的作用。