2-[(1S,2R,6S,7R)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]-N-quinolin-8-ylacetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[(1S,2R,6S,7R)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]-N-quinolin-8-ylacetamide
• 化学式: C₂₀H₁₇N₃O₃
• 分子量: 347.373
• InChiKey: OOLKTTDABBHCLL-AZQPONJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.37
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 ammonium hydroxide 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 52.0h， 生成 2-[(1S,2R,6S,7R)-3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl]-N-quinolin-8-ylacetamide
  参考文献：
  名称：

  Quinoline-functionalized norbornene for fluorescence recognition of metal ions

  摘要：

  A quinoline-functionalized norbornene (1) and its homopolymer (P1) for metal ions recognition have been synthesized and characterized. In CH3CN solution, 1 exhibited fluorescence enhancement response toward Hg2+, Zn2+ and Cu2+, with Hg2+ resulting in a green emission at 465 nm, and Zn2+/Cu2+ increasing l's original emission at 406 nm. NMR titrations and DFF calculations results indicated that 1 bound Hg2+ in an imidic acid tautomeric form of the amide quinoline receptor, while Zn2+ and Cu2+ were bound to 1 in an amide tautomeric form. In addition, owing to the strong imidic acid tautomeric binding mode of 1-He2+ complex, 1 can recognized Hg2+ from Zn2+/Cu2+ and other competitive metal ions. In contrast, the homopolymer P1, which was obtained by ring opening metathesis polymerization (ROMP) method, exhibited only fluorescence enhancement sensing to Hg2+ and Cu2+ in an amide tautomeric binding mode with increasing emission at 416 nm. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2015.03.003