(Z)-2-(2'-chloroethenyl)quinoline | 1144527-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (Z)-2-(2'-chloroethenyl)quinoline
• 英文别名: 2-[(Z)-2-chloroethenyl]quinoline
• CAS: 1144527-65-0
• 化学式: C₁₁H₈ClN
• 分子量: 189.644
• InChiKey: DNCAKVDLLVQCLL-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2'-chloroethenyl)quinoline 在 bis(triphenylphosphine)nickel(II) chloride 、 四丁基碘化铵 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到1,4-Di(2-chinolyl)-1,3-butadien
  参考文献：
  名称：

  Synthesis of conjugated (1E,3E)- and (1Z,3Z)-1,4-di(n-pyridyl) (or n-quinolyl)-1,3-butadienes from n-(2′-chloroethenyl)pyridine (or quinoline)

  摘要：

  The homocoupling reaction between the conjugated n-(2-chloroethenyl)pyridine; n, 2-, 3- and 4- (or quinoline; n, 2- and 4-) mediated by zero-valent nickel complexes at room temperature affords to the corresponding 1,4-diaryl-1,3-butadiene, always as the 1E,3E stereoisomer. The yield in 1,4-diaryl-1,3-butadiene increases with the nickel catalyst and hence, the active zero-valent nickel catalyst is not regenerated during the homocoupling reaction.The stereospecific synthesis of (1Z,3Z)-1,4-di(4'-pyridyl)-1,3-butadiene stereoisomer was efficiently carried Out by partial hydrogenation of the appropriate 1,4-di(4'-pyridyl)-1,3-butadiyne. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.050
• 作为产物：
  描述：

  喹啉-2-甲醛 、 (氯甲基)三苯基氯化磷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 以43%的产率得到(E)-2-(2'-chloroethenyl)quinoline
  参考文献：
  名称：

  Synthesis of conjugated (1E,3E)- and (1Z,3Z)-1,4-di(n-pyridyl) (or n-quinolyl)-1,3-butadienes from n-(2′-chloroethenyl)pyridine (or quinoline)

  摘要：

  The homocoupling reaction between the conjugated n-(2-chloroethenyl)pyridine; n, 2-, 3- and 4- (or quinoline; n, 2- and 4-) mediated by zero-valent nickel complexes at room temperature affords to the corresponding 1,4-diaryl-1,3-butadiene, always as the 1E,3E stereoisomer. The yield in 1,4-diaryl-1,3-butadiene increases with the nickel catalyst and hence, the active zero-valent nickel catalyst is not regenerated during the homocoupling reaction.The stereospecific synthesis of (1Z,3Z)-1,4-di(4'-pyridyl)-1,3-butadiene stereoisomer was efficiently carried Out by partial hydrogenation of the appropriate 1,4-di(4'-pyridyl)-1,3-butadiyne. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.01.050

文献信息

• Synthesis of conjugated (1E,3E)- and (1Z,3Z)-1,4-di(n-pyridyl) (or n-quinolyl)-1,3-butadienes from n-(2′-chloroethenyl)pyridine (or quinoline)
  作者：J.G. Rodríguez、Cristina Díaz-Oliva

  DOI：10.1016/j.tet.2009.01.050

  日期：2009.3

  The homocoupling reaction between the conjugated n-(2-chloroethenyl)pyridine; n, 2-, 3- and 4- (or quinoline; n, 2- and 4-) mediated by zero-valent nickel complexes at room temperature affords to the corresponding 1,4-diaryl-1,3-butadiene, always as the 1E,3E stereoisomer. The yield in 1,4-diaryl-1,3-butadiene increases with the nickel catalyst and hence, the active zero-valent nickel catalyst is not regenerated during the homocoupling reaction.The stereospecific synthesis of (1Z,3Z)-1,4-di(4'-pyridyl)-1,3-butadiene stereoisomer was efficiently carried Out by partial hydrogenation of the appropriate 1,4-di(4'-pyridyl)-1,3-butadiyne. (C) 2009 Elsevier Ltd. All rights reserved.