4-(2-(((4-methyl-1H-imidazol-5-yl)methylene)amino)ethyl)benzene-1,2-diol | 1363301-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-(((4-methyl-1H-imidazol-5-yl)methylene)amino)ethyl)benzene-1,2-diol
• 英文别名: 4-[2-[(5-methyl-1H-imidazol-4-yl)methylideneamino]ethyl]benzene-1,2-diol
• CAS: 1363301-25-0
• 化学式: C₁₃H₁₅N₃O₂
• 分子量: 245.281
• InChiKey: KJJKLZKSLAOGGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  81.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  盐酸多巴胺 、 5-甲基咪唑-4-甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.5h， 以98%的产率得到4-(2-(((4-methyl-1H-imidazol-5-yl)methylene)amino)ethyl)benzene-1,2-diol
  参考文献：
  名称：

  New emissive dopamine derivatives as fluorescent chemosensors for metal ions: A CHEF effect for Al(III) interaction

  摘要：

  Three new Schiff-base ligands 1-3 derivatives from neurotransmitter dopamine, bearing an indazole (1), methylimidazole (2) or hydroxynaphthaldehyde (3) units were successfully synthesized and characterized by elemental analysis, H-1 NMR, C-13 NMR, IR (infrared), ESI-TOF (electrospray ionization-time of flight-mass), UV-Vis absorption and emission spectroscopy. The interaction with the metal ions Li+, Na+, Mg2+, Ca2+, Zn2+, Cd2+, Cu2+, Ni2+, Ag+, Fe3+ and Al3+ has been explored by absorption and fluorescence emission spectroscopy. Compound 3 shows to be the most emissive one, with a quantum yield of 0.022, followed by compound 2 (phi = 0.009) and 1 (phi = 0.001). Compound 1 reveals quite selective for Al3+, generating an emissive complex formed by three units of 1 per metal ion. On the other hand compound 3, shows a ratiometric effect with Al3+ appearing as a new emission band centred at 530 nm. With the other transition and post-transition metal ions, a quenching in the emission was observed, being 3 the most sensitive one, being quenched by 0.34 ppm of Zn2+ and Cu2+, 0.48 ppm of Ni2+, 0.061 ppm of Fe3+ and 0.047 ppm of Al3+. In most cases a stoichiometry of three ligands by one metal ion was postulated. In order to study the fluorescence properties in the solid state, the Al3+ metal complexes of 1 (4) and 3 (5) were synthesized as new emissive materials. In both cases a very strong emissive systems were obtained, with a quantum yield of 0.01 and 0.04 for 4 and 5. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.08.033