5-(diethylamino)-2-(5-nitro-1H-benzo[d]imidazol-2-yl)phenol | 1321917-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-(diethylamino)-2-(5-nitro-1H-benzo[d]imidazol-2-yl)phenol
• 英文别名: 5-(N,N-diethylamino)-2-(5-nitro-1H-benzimidazol-2-yl)phenol
• CAS: 1321917-83-2
• 化学式: C₁₇H₁₈N₄O₃
• 分子量: 326.355
• InChiKey: ZFIKGYTXSNKTNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  95.29
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(diethylamino)-2-(5-nitro-1H-benzo[d]imidazol-2-yl)phenol 在 sodium hypochlorite 作用下， 生成
  参考文献：
  名称：

  Synthesis, characterization, and supramolecular architectures of two distinct classes of probes for the visualization of endogenously generated hypochlorite ions in response to cellular activity

  摘要：

  Two distinct classes of compounds, (E)-2-(((3-amino-4-nitrophenyl) imino) methyl)-5-(diethylamino) phenol (SB) and 5-(diethylamino)-2-(5-nitro-1H-benzo[d]imidazol-2-yl) phenol (IM) were synthesized. SB, a bright red colored compound was crystallized in acetonitrile as a triclinic crystal system while IM, yellow colored compound crystallized as a monoclinic crystal system in dimethylformamide by vapor diffusion of diethylether. These compounds were characterized using spectroscopic techniques (IR, UV-visible, H-1, and C-13 NMR), and X-ray crystallography. SB and IM displayed classical and non-classical H-bonding involving C-H center dot center dot center dot O and pi center dot center dot center dot pi interactions. These compounds detected hypochlorite ions in aqueous HMSO (1:9, v/v, HEPES buffer, pH 7.4), and detection was visible via color changes by naked eye. We also performed UV-visible and fluorescence titrations, showing detection limits of 8.82 x 10(-7) M for SB and 2.44 x 10(-7) M for IM. The fluorometric responses from SB and IM were also studied against different ROS and anions. DFT calculations were performed to strengthen the proposed sensing mechanisms of both SB and IM. Hypochlorite, which is endogenously generated by myeloperoxidase in endosomes, was specifically visualized using SB and IM in lipopolysaccharide-treated RAW264.7 cells. These probes were also used to image the generation of hypochlorite by RAW264.7 cells during phagocytosis of non-fluorescent polystyrene beads.

  DOI：

  10.1016/j.jphotobiol.2019.111594
• 作为产物：
  描述：

  3-羟基-N,N-二乙基苯胺 在 三氯氧磷 、 三氯化磷 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-(diethylamino)-2-(5-nitro-1H-benzo[d]imidazol-2-yl)phenol
  参考文献：
  名称：

  受ESIPT启发的2-取代苯并咪唑、苯并恶唑和苯并噻唑荧光衍生物的合成和光物理特性

  摘要：

  新型2-( 1H-苯并咪唑-2-基)-5-( N,N-二乙氨基)苯酚，2-(1,3-苯并恶唑-2-基)-5-( N,N-二乙氨基)苯酚， 2-（1,3-苯并噻唑-2-基）-5-（N，N-二乙基氨基）苯酚和它们的衍生物已经从合成对-N，N-二乙基氨基水杨醛与不同的取代ö苯二胺或ö氨基苯酚或ö研究了氨基苯硫酚及其光物理性质。研究了溶剂极性对合成化合物吸收发射特性的影响。所有这些化合物都显示出具有单吸收和双发射特性的激发态分子内质子转移途径。荧光化合物通过FT-IR、1 HNMR、13 C NMR和质谱分析表征。TGA 分析表明，这些化合物在高达 200 °C 的温度下都是热稳定的。

  DOI：

  10.1007/s10895-011-0962-8