(Z)-3-Iodopropenenitrile | 137627-62-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-3-Iodopropenenitrile
• 英文别名: 3-iodopropenitrile；(Z)-3-Iodo-acrylonitrile；(Z)-3-iodoprop-2-enenitrile
• CAS: 137627-62-4
• 化学式: C₃H₂IN
• 分子量: 178.96
• InChiKey: KEMRYSHXNAFVLX-UPHRSURJSA-N

物化性质

• 沸点：
  183.3±23.0 °C(Predicted)
• 密度：
  2.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-苯基-1-丙炔 、 (Z)-3-Iodopropenenitrile 在 正丁基锂 、 mercury dichloride 、 zinc dibromide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.87h， 以90%的产率得到6-phenylhex-5-yn-2(Z)-enitrile
  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
• 作为产物：
  描述：

  丙炔腈 在 溶剂黄146 、 lithium iodide 作用下， 反应 24.0h， 以98%的产率得到(Z)-3-Iodopropenenitrile
  参考文献：
  名称：

  A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives

  摘要：

  2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products. A rationale for the regio- and stereospecificity is briefly discussed.

  DOI：

  10.1021/jo00028a055

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.
• A novel regio- and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives
  作者：Shengming Ma、Xiyan Lu、Zhigang Li

  DOI：10.1021/jo00028a055

  日期：1992.1

  2-Propynoic acid and its derivatives are hydrohalogenated regio- and stereospecifically by reaction with lithium halides in acetic acid, or preferably with 1 equiv of acetic acid in refluxing CH3CN, to afford the thermodynamically unfavorable (Z)-3-halopropenoic acids and their derivatives as sole products. A rationale for the regio- and stereospecificity is briefly discussed.