4-{(Z)-2-[4-((E)-2-Bromo-vinyl)-phenyl]-vinyl}-pyridine | 543745-19-3

• 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: 4-{(Z)-2-[4-((E)-2-Bromo-vinyl)-phenyl]-vinyl}-pyridine
• CAS: 543745-19-3
• 化学式: C₁₅H₁₂BrN
• 分子量: 286.171
• InChiKey: RQSGOCYTTTUROS-PPHVVYHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-{(Z)-2-[4-((E)-2-Bromo-vinyl)-phenyl]-vinyl}-pyridine 在 吡啶 、 copper(I) chloride 、 potassium tert-butylate 、 氧气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 4-[(Z)-2-[4-[4-[4-[(Z)-2-pyridin-4-ylethenyl]phenyl]buta-1,3-diynyl]phenyl]ethenyl]pyridine
  参考文献：
  名称：

  π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes

  摘要：

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01628-9
• 作为产物：
  描述：

  (E)-1-(2-溴乙烯基)-4-甲基苯 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 32.5h， 生成 4-{(Z)-2-[4-((E)-2-Bromo-vinyl)-phenyl]-vinyl}-pyridine
  参考文献：
  名称：

  π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes

  摘要：

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01628-9

文献信息

• π-Extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge–transfer complexes
  作者：J.Gonzalo Rodrı́guez、Rosa Martı́n-Villamil、Antonio Lafuente

  DOI：10.1016/s0040-4020(02)01628-9

  日期：2003.2

  The conjugate (E)- and (Z)-(4'-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4'-pyridylethenyl-4-phenyi-beta-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4'-pyridylethenyl)-4-phenyll-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono-and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. (C) 2003 Elsevier Science Ltd. All rights reserved.