6-(4-cyano-phenylvinylene)-3-bromopyridine | 604005-15-4

• 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: 6-(4-cyano-phenylvinylene)-3-bromopyridine
• 英文别名: 4-[(E)-2-(5-bromopyridin-2-yl)ethenyl]benzonitrile
• CAS: 604005-15-4
• 化学式: C₁₄H₉BrN₂
• 分子量: 285.143
• InChiKey: NLABJQOHDMEWAC-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(4-cyano-phenylvinylene)-3-bromopyridine 在 四(三苯基膦)钯 、 氢氟酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 53.0h， 生成 4-[(E)-2-(6'-{(E)-2-[5-(2-Hydroxy-ethyl)-thiophen-2-yl]-vinyl}-5'-methyl-[3,3']bipyridinyl-6-yl)-vinyl]-benzonitrile
  参考文献：
  名称：

  6-(Arylvinylene)-3-pyridinylboronic esters. Part 2: Versatile building blocks for push–pull nonlinear optical chromophores

  摘要：

  This paper describes a general approach for the synthesis of push-pull 6,6'-disubstituted-3,3'-bipyridine chromophores. As examples, 6-(4-ethanol-2-thienylvinylene)-5-methyl-3-bromopyridine, 6-(4-hydroxy-phenylvinylene)-5-methyl-3-bromopyridine, and the corresponding 3-pyridinylboronic esters have been prepared as building blocks end-capped with electron donor groups (D). 6-(4-Cyano-phenylvinylene)-5-methyl-3-bromopyridine, and 6-(4-cyano-phenylvinylene)-3-bromopyridine have been synthesized as building blocks end-capped with electron acceptor groups (A). {A x D} type cross-couplings via Suzuki reaction gave the push-pull chromophores (I) and (II) in high yields and multigram scales. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01427-8
• 作为产物：
  描述：

  5-溴-2-甲基吡啶 、 4-氰基苯甲醛 在 对甲苯磺酸 作用下， 以31%的产率得到6-(4-cyano-phenylvinylene)-3-bromopyridine
  参考文献：
  名称：

  6-(Arylvinylene)-3-pyridinylboronic esters. Part 2: Versatile building blocks for push–pull nonlinear optical chromophores

  摘要：

  This paper describes a general approach for the synthesis of push-pull 6,6'-disubstituted-3,3'-bipyridine chromophores. As examples, 6-(4-ethanol-2-thienylvinylene)-5-methyl-3-bromopyridine, 6-(4-hydroxy-phenylvinylene)-5-methyl-3-bromopyridine, and the corresponding 3-pyridinylboronic esters have been prepared as building blocks end-capped with electron donor groups (D). 6-(4-Cyano-phenylvinylene)-5-methyl-3-bromopyridine, and 6-(4-cyano-phenylvinylene)-3-bromopyridine have been synthesized as building blocks end-capped with electron acceptor groups (A). {A x D} type cross-couplings via Suzuki reaction gave the push-pull chromophores (I) and (II) in high yields and multigram scales. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01427-8

文献信息

• 6-(Arylvinylene)-3-pyridinylboronic esters. Part 2: Versatile building blocks for push–pull nonlinear optical chromophores
  作者：Nicolas Leclerc、Laurent Galmiche、André-Jean Attias

  DOI：10.1016/s0040-4039(03)01427-8

  日期：2003.7

  This paper describes a general approach for the synthesis of push-pull 6,6'-disubstituted-3,3'-bipyridine chromophores. As examples, 6-(4-ethanol-2-thienylvinylene)-5-methyl-3-bromopyridine, 6-(4-hydroxy-phenylvinylene)-5-methyl-3-bromopyridine, and the corresponding 3-pyridinylboronic esters have been prepared as building blocks end-capped with electron donor groups (D). 6-(4-Cyano-phenylvinylene)-5-methyl-3-bromopyridine, and 6-(4-cyano-phenylvinylene)-3-bromopyridine have been synthesized as building blocks end-capped with electron acceptor groups (A). A x D} type cross-couplings via Suzuki reaction gave the push-pull chromophores (I) and (II) in high yields and multigram scales. (C) 2003 Elsevier Ltd. All rights reserved.