4-methyl-1-(2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl)pyridinium bromide | 1515876-39-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 4-methyl-1-(2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl)pyridinium bromide
• 英文别名: 4-Methyl-1-{2-oxo-2-[4-(2-oxo-2h-chromen-3-yl)phenyl]ethyl}pyridinium bromide；3-[4-[2-(4-methylpyridin-1-ium-1-yl)acetyl]phenyl]chromen-2-one;bromide
• CAS: 1515876-39-7
• 化学式: Br*C₂₃H₁₈NO₃
• 分子量: 436.305
• InChiKey: AFXKXFUKRKFLKK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-1-(2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl)pyridinium bromide 、 对二甲氨基苯甲醛 在 乙酸酐 作用下， 反应 1.17h， 以57%的产率得到4-{2-[4-(dimethylamino)phenyl]ethenyl}-1-{2-[4-(dimethylamino)phenyl]-1-[4-(2-oxo-2H-chromen-3-yl)benzoyl]ethenyl}pyridinium bromide
  参考文献：
  名称：

  New biscyanine dye based on 1-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}-4-methylpyridinium bromide. Electron transitions and electronic spectra

  摘要：

  New biscyanine dye, 4-{2-[4-(dimethylamino)phenyl]ethenyl}-1-{2-[4-(dimethylamino)phenyl]-1-[4-(2-oxo-2H-chromen-3-yl)benzoyl]ethenyl}pyridinium bromide, has been prepared via condensation of 4-dimethylaminobenzaldehyde with 4-methyl-1-{2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl}pyridinium bromide. The latter has been synthesized via the Meerwein reaction of coumarin with 4-acetylphenyldiazonium chloride with subsequent bromination and quaternization of the formed alpha-bromoketone under the action of 4-methylpyridine. Electronic spectra are analyzed, and quantum-chemical simulation of possible isomers of the biscyanine dye has been performed.

  DOI：

  10.1134/s1070363214110127
• 作为产物：
  描述：

  4-acetylphenyldiazonium chloride 在 copper(II) choride dihydrate 、 溴 作用下， 以 水 、 溶剂黄146 、 丙酮 、 甲苯 为溶剂， 反应 2.0h， 生成 4-methyl-1-(2-oxo-2-[4-(2-oxo-2H-chromen-3-yl)phenyl]ethyl)pyridinium bromide
  参考文献：
  名称：

  Synthesis of nitrogen heterocycles underlain by application of 3-(4-Acetyl[phenyl)-2H-coumarin

  摘要：

  3-(4-Acetylphenyl)-2H-chromen-2-one was obtained from 4-acetylphenyldiazonium chloride in the conditions of Meerwein reaction. Reactions of 3-[4-(2-bromoacetyl)phenyl]-2H-chromen-2-one with pyridine, 4-methylpyridine, quinoline, benzo[f]quinoline, and triphenylphosphine afforded quaternary salts, and with thioacetamide, thiourea, 2-aminopyridine, 2-aminopyrimidine, and 6-aminopurine provided the corresponding derivatives of thiazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, imidazo[2,1-i]purine. In the reaction of the same bromo derivative with thiosemicarbazide and aromatic aldehydes a thiazole ring is built and the corresponding hydrazones are formed.

  DOI：

  10.1134/s1070428013110158