2-(1H-苯并咪唑-2-基)-3-羟基-4H-色烯-4-酮 | 1037300-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 2-(1H-苯并咪唑-2-基)-3-羟基-4H-色烯-4-酮
• 英文名称: 2-(1H-benzimidazol-2-yl)-3-hydroxy-4H-chromen-4-one
• 英文别名: 2(1h-Benzimidazol-2-yl)-3-hydroxy-4h-chromen-4-one；2-(1H-benzimidazol-2-yl)-3-hydroxychromen-4-one
• CAS: 1037300-44-9
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: CDTBDEOHTZVRFE-UHFFFAOYSA-N

物化性质

• 沸点：
  478.0±55.0 °C(predicted)
• 密度：
  1.546±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1H-苯并咪唑-2-基)-3-羟基-4H-色烯-4-酮 、 mercury(II) diacetate 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Mercury Ions Complexation with a Series of Heterocyclic Derivatives of 3-Hydroxychromone: Spectral Effects and Prospects for Ultrasensitive Hg²⁺ Probing

  摘要：

  Complexation of three 3-hydroxychromone derivatives bearing a nitrogen-containing heterocyclic moiety in the position 2 of the chromone bicycle - benzimidazole, quinoline, and 2,5-diphenyloxazole, with mercury(II) ions is reported. Formation of chelate complexes with the metal cations coordinated with the cavity formed by 3-OH and 4-C=O groups was shown, as well as the possibility of side moiety heteroatom participation in binding of metal ions. High sensitivity to mercury of 2,5-diphenyloxazole-substituted 3-hydroxychromone was elucidated, allowing to detect Hg2+ below the maximum permissible concentration for drinking water. This makes the above-mentioned compound a prospective basis for development of sensors for ultralow mercury concentration detection in water. Unusual fluorescence ignition of 2-(quinolin-2-yl)-3-hydroxychromone at low Hg2+ concentrations, rarely observed for heavy metals ions complexation with organic fluorescent ligands, was discussed.

  DOI：

  10.1021/jp110974n
• 作为产物：
  描述：

  3-(1H-benzimidazol-2-yl)-1-(2-hydroxyphenyl)-2-propen-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 以62%的产率得到2-(1H-苯并咪唑-2-基)-3-羟基-4H-色烯-4-酮
  参考文献：
  名称：

  New benzimidazolic 3-hydroxychromone derivative with two alternative mechanisms of the excited state intramolecular proton transfer reaction

  摘要：

  The 2-(benzimidazol-2-yl) derivative of 3-hydroxychromone was synthesized and studied by X-ray structure analysis, H-1 NMR and fluorescence spectroscopy. The possibility of the alternative H-bonds formation and thus - two alternative mechanisms of the excited state intramolecular proton transfer reaction was discussed on the base of the spectral data, X-ray structure analysis and quantum-chemical calculations. (C) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2007.09.009