N-((propylamino)(quinolin-6-ylamino)methylene)benzamide | 1216865-88-1

• 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: N-((propylamino)(quinolin-6-ylamino)methylene)benzamide
• 英文别名: N-(N'-propyl-N-quinolin-6-ylcarbamimidoyl)benzamide
• CAS: 1216865-88-1
• 化学式: C₂₀H₂₀N₄O
• 分子量: 332.405
• InChiKey: SONMTLPDWBKGER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-((propylamino)(quinolin-6-ylamino)methylene)benzamide 反应 0.25h， 以65%的产率得到1-phenyl-3-propylaminopyrido[3,2-f]quinazoline
  参考文献：
  名称：

  Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of N-Heterocyclic Carbene in the Key Cyclization Step

  摘要：

  An original route to 2-alkyamino-4-phenylquinazolines in three steps from simple (hetero)aromatic amines is reported here. The key step involves the intramolecular cyclization of benzoyl arylguanidines performed in [OMIm]Cl ionic liquid. The basic (hetero)aromatic guanidines deprotonate the imidazolium-based Ionic liquid, thus triggering the cascade process ultimately leading to the intramolecular cyclization. This reaction is the first example of a Friedel-Crafts-type reaction in which an N-heterocyclic carbene is involved in the formation of the electrophilic intermediate.

  DOI：

  10.1021/jo902726k
• 作为产物：
  描述：

  正丙胺 、 N-benzoyl-N'-(6-quinolinyl)thiourea 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-((propylamino)(quinolin-6-ylamino)methylene)benzamide
  参考文献：
  名称：

  Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of N-Heterocyclic Carbene in the Key Cyclization Step

  摘要：

  An original route to 2-alkyamino-4-phenylquinazolines in three steps from simple (hetero)aromatic amines is reported here. The key step involves the intramolecular cyclization of benzoyl arylguanidines performed in [OMIm]Cl ionic liquid. The basic (hetero)aromatic guanidines deprotonate the imidazolium-based Ionic liquid, thus triggering the cascade process ultimately leading to the intramolecular cyclization. This reaction is the first example of a Friedel-Crafts-type reaction in which an N-heterocyclic carbene is involved in the formation of the electrophilic intermediate.

  DOI：

  10.1021/jo902726k