2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinoline | 42143-08-8

• 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: 2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinoline
• 英文别名: 2-furan-2-yl-3-methyl-3H-imidazo[4,5-f]quinoline；2-(furan-2-yl)-3-methylimidazo[4,5-f]quinoline
• CAS: 42143-08-8
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: IAVJFWAUEXOIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinoline 在 溴 、 溶剂黄146 、 sodium nitrite 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 3-methyl-2-(5-nitrofuran-2-yl)-3H-imidazo-[4,5-f]quinoline
  参考文献：
  名称：

  2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline. Synthesis and electrophilic substitution reactions

  摘要：

  2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline was synthesized by the Weidenhagen reaction of quinoline-5,6-diamine with furfural. Its alkylation with methyl iodide in the system KOH-DMSO gave two isomeric N-methyl derivatives, 2-(2-furyl)-1-methyl-1H- and 2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinolines, the latter prevailing. 2-(2-Furyl)-3-methyl-3H-imidazo[4,5-f] quinoline was brought into electrophilic substitution reactions: bromination, nitration, formylation, acylation, sulfonation. Depending on the reaction conditions, electrophilic attack could be directed at both furan ring and quinoline fragment.

  DOI：

  10.1134/s1070428011010155
• 作为产物：
  描述：

  糠醛 在 copper diacetate 、 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 2.0h， 生成 2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinoline 、 2-(2-furyl)-1-methyl-1H-imidazo[4,5-f]quinoline
  参考文献：
  名称：

  2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline. Synthesis and electrophilic substitution reactions

  摘要：

  2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline was synthesized by the Weidenhagen reaction of quinoline-5,6-diamine with furfural. Its alkylation with methyl iodide in the system KOH-DMSO gave two isomeric N-methyl derivatives, 2-(2-furyl)-1-methyl-1H- and 2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinolines, the latter prevailing. 2-(2-Furyl)-3-methyl-3H-imidazo[4,5-f] quinoline was brought into electrophilic substitution reactions: bromination, nitration, formylation, acylation, sulfonation. Depending on the reaction conditions, electrophilic attack could be directed at both furan ring and quinoline fragment.

  DOI：

  10.1134/s1070428011010155

文献信息

• Synthesis and transformations of 2-(2-furyl)- and 2-[?-(2-furyl)vinyl]imidazo[4,5-f]quinolines
  作者：F. T. Pozharskii、L. Ya. Oleinikova

  DOI：10.1007/bf00471512

  日期：1973.4