(E)-4-(2-(pyridin-4-yl)vinyl)-8-tosyloxyquinoline | 1166262-18-5

• 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: (E)-4-(2-(pyridin-4-yl)vinyl)-8-tosyloxyquinoline
• 英文别名: [4-[(E)-2-pyridin-4-ylethenyl]quinolin-8-yl] 4-methylbenzenesulfonate
• CAS: 1166262-18-5
• 化学式: C₂₃H₁₈N₂O₃S
• 分子量: 402.474
• InChiKey: ILJNVVYRLMCZAJ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-4-(2-(pyridin-4-yl)vinyl)-8-tosyloxyquinoline 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以92%的产率得到(E)-4-(2-(pyridin-4-yl)vinyl)quinolin-8-ol
  参考文献：
  名称：

  Synthesis of 4-(2-arylvinyl)-8-hydroxyquinolines via anhydrous Heck coupling reaction and the PL properties of their Al complexes

  摘要：

  Anhydrous Heck coupling between 2 and eight different arylvinyl compounds using 3 mol % of PdCl2/2PPh(3) catalyst system occurs selectively at position-4 of 2 affording 4-(2-arylvinyl)-8-tosyloxyquinolines 3 in good to high yields. The tosyloxy protecting group showed high stability under anhydrous coupling conditions. Deprotection of the resulting 4-arylvinyl-8-tosyloxyquinolines produced 4-(2-arylvinyl)-8-hydroxyquinolines 4 in high yields. The aluminium complexes of the resulting 8-hydroxyquinolines have been synthesized and their photoluminescence (PL) properties have been studied. One of the complexes with a 2,4,6-trimethoxystyryl substituent at position-4 of the quinolate shows higher relative PL quantum yield than the other complexes due to the minimization of the cis-trans photo-isomerization in solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.028
• 作为产物：
  描述：

  4-乙烯基吡啶 、 4-bromoquinolin-8-yl 4-methylbenzenesulfonate 在 potassium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(E)-4-(2-(pyridin-4-yl)vinyl)-8-tosyloxyquinoline
  参考文献：
  名称：

  Synthesis of 4-(2-arylvinyl)-8-hydroxyquinolines via anhydrous Heck coupling reaction and the PL properties of their Al complexes

  摘要：

  Anhydrous Heck coupling between 2 and eight different arylvinyl compounds using 3 mol % of PdCl2/2PPh(3) catalyst system occurs selectively at position-4 of 2 affording 4-(2-arylvinyl)-8-tosyloxyquinolines 3 in good to high yields. The tosyloxy protecting group showed high stability under anhydrous coupling conditions. Deprotection of the resulting 4-arylvinyl-8-tosyloxyquinolines produced 4-(2-arylvinyl)-8-hydroxyquinolines 4 in high yields. The aluminium complexes of the resulting 8-hydroxyquinolines have been synthesized and their photoluminescence (PL) properties have been studied. One of the complexes with a 2,4,6-trimethoxystyryl substituent at position-4 of the quinolate shows higher relative PL quantum yield than the other complexes due to the minimization of the cis-trans photo-isomerization in solution. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.028

文献信息

• Synthesis of 4-(2-arylvinyl)-8-hydroxyquinolines via anhydrous Heck coupling reaction and the PL properties of their Al complexes
  作者：Walaa A.E. Omar、Osmo E.O. Hormi

  DOI：10.1016/j.tet.2009.03.028

  日期：2009.5

  Anhydrous Heck coupling between 2 and eight different arylvinyl compounds using 3 mol % of PdCl2/2PPh(3) catalyst system occurs selectively at position-4 of 2 affording 4-(2-arylvinyl)-8-tosyloxyquinolines 3 in good to high yields. The tosyloxy protecting group showed high stability under anhydrous coupling conditions. Deprotection of the resulting 4-arylvinyl-8-tosyloxyquinolines produced 4-(2-arylvinyl)-8-hydroxyquinolines 4 in high yields. The aluminium complexes of the resulting 8-hydroxyquinolines have been synthesized and their photoluminescence (PL) properties have been studied. One of the complexes with a 2,4,6-trimethoxystyryl substituent at position-4 of the quinolate shows higher relative PL quantum yield than the other complexes due to the minimization of the cis-trans photo-isomerization in solution. (C) 2009 Elsevier Ltd. All rights reserved.