2-amino-5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile | 1401023-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile
• CAS: 1401023-53-7
• 化学式: C₂₂H₁₄N₄
• 分子量: 334.38
• InChiKey: NFTPNDIRIMYFKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.11
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-amino-5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以61%的产率得到2-amino-5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile hydrochloride
  参考文献：
  名称：

  Synthesis, crystal structure and spectroscopic study of novel benzimidazoles and benzimidazo[1,2-a]quinolines as potential chemosensors for different cations

  摘要：

  In this manuscript the synthesis, crystal structure, spectroscopic characterization and titration with several metal chloride salts of novel E-3-phenyl-2-(1-phenylbenzimidazol-2-yl)acrylonitriles and 5-phenylbenzimidazo[1,2-a]quinoline derivatives are described. All compounds were characterized by means of H-1, C-13 NMR, MS, UV/Vis and fluorescence spectroscopy.Crystal and molecular structures of E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile were determined by single-crystal X-ray diffractometry. The molecular assembly is characterized by the C-H center dot center dot center dot-O and C-H center dot center dot center dot N intermolecular hydrogen bonds in E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo [1,2-a]quinoline-6-carbonitrile, respectively.Spectroscopic characterization of the prepared compounds was performed by using UV/Vis and fluorescence spectroscopy in ethanol. In order to determine a selectivity towards a variety of cations, to explore their use as potential chemosensors, the amino substituted 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile was chosen for a titration with metal chloride salts using fluorescence spectroscopy. The fluorescence intensity significantly increased upon addition of Zn2+ and Ag+ cations while decreased by addition of Mn2+, Co2+, Cu2+, Hg+, Li+ and Fe3+ cations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.05.024
• 作为产物：
  描述：

  邻氨基二苯胺 在 哌啶 、 盐酸 、 tin(II) chloride dihdyrate 、 碘 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 7.33h， 生成 2-amino-5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis, crystal structure and spectroscopic study of novel benzimidazoles and benzimidazo[1,2-a]quinolines as potential chemosensors for different cations

  摘要：

  In this manuscript the synthesis, crystal structure, spectroscopic characterization and titration with several metal chloride salts of novel E-3-phenyl-2-(1-phenylbenzimidazol-2-yl)acrylonitriles and 5-phenylbenzimidazo[1,2-a]quinoline derivatives are described. All compounds were characterized by means of H-1, C-13 NMR, MS, UV/Vis and fluorescence spectroscopy.Crystal and molecular structures of E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile were determined by single-crystal X-ray diffractometry. The molecular assembly is characterized by the C-H center dot center dot center dot-O and C-H center dot center dot center dot N intermolecular hydrogen bonds in E-3-(4-nitrophenyl)-2-(1-phenyl-benzimidazol-2-yl)acrylonitrile and 5-phenylbenzimidazo [1,2-a]quinoline-6-carbonitrile, respectively.Spectroscopic characterization of the prepared compounds was performed by using UV/Vis and fluorescence spectroscopy in ethanol. In order to determine a selectivity towards a variety of cations, to explore their use as potential chemosensors, the amino substituted 5-phenylbenzimidazo[1,2-a]quinoline-6-carbonitrile was chosen for a titration with metal chloride salts using fluorescence spectroscopy. The fluorescence intensity significantly increased upon addition of Zn2+ and Ag+ cations while decreased by addition of Mn2+, Co2+, Cu2+, Hg+, Li+ and Fe3+ cations. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.05.024