4-(2-(((2-hydroxynaphthalen-1-yl)methylene)amino)ethyl)benzene-1,2-diol | 1066693-08-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(2-(((2-hydroxynaphthalen-1-yl)methylene)amino)ethyl)benzene-1,2-diol
• 英文别名: 4-[2-[(2-Hydroxynaphthalen-1-yl)methylideneamino]ethyl]benzene-1,2-diol
• CAS: 1066693-08-0
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: XMIANJPETBQODT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  73
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  多巴胺 、 2-羟基-1-萘甲醛 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 4-(2-(((2-hydroxynaphthalen-1-yl)methylene)amino)ethyl)benzene-1,2-diol
  参考文献：
  名称：

  Power of Dopamine: Multifunctional Compound Assisted Conversion of the Most Risk Factor into Therapeutics of Alzheimer’s Disease

  摘要：

  DOI：

  10.1021/acschemneuro.3c00777

文献信息

• New emissive dopamine derivatives as fluorescent chemosensors for metal ions: A CHEF effect for Al(III) interaction
  作者：Elisabete Oliveira、Hugo M. Santos、José Luis Capelo、Carlos Lodeiro

  DOI：10.1016/j.ica.2011.08.033

  日期：2012.2

  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.