N-(6-hydroxy-2-methyl-8-quinolyl)trifluoroacetamide | 356524-69-1

• 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: N-(6-hydroxy-2-methyl-8-quinolyl)trifluoroacetamide
• 英文别名: 2,2,2-trifluoro-N-(6-hydroxy-2-methylquinolin-8-yl)acetamide
• CAS: 356524-69-1
• 化学式: C₁₂H₉F₃N₂O₂
• 分子量: 270.211
• InChiKey: FBIJCGSQPRJNNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(6-hydroxy-2-methyl-8-quinolyl)trifluoroacetamide 在 吡啶 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 14.0h， 生成 ethyl-2-(2-methyl-6-quinolyloxy-8-(2,2,2-trifluoroethyl)sulfonamido)acetate
  参考文献：
  名称：

  摘要：

  Zinc(II) specific fluorophores are of substantial importance in the study of intracellular Zn2+. Two such widely used fluorophores are 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid, Zinquin (1), and its ethyl ester, Zinquin ester (2), which fluoresce strongly when bound by Zn2+. To gain insight into the factors affecting the fluorescence of such fluorophores the closely related 4-methyl-N-(6-methoxy-2-methyl-8-quinolyl)-benzenesulfonamide (3), and nine analogues (4-12), substituted at sulfur by nine different substituents have been prepared and their fluorescing characteristics and those of their Zn2+ complexes have been examined. The nine substituents are: 2,2,2-trifluoroethyl (4), 4-methoxyphenyl (5), 4-acetamidophenyl (6), 4-bromophenyl (7), 4-nitrophenyl (8), 3-trifluoromethylphenyl (9), naphth-1-yl (10), naphth-2-yl (11) and 5-dimethylaminonaphth-1-yl (12). Under neutral conditions in 75/25% v/v ethanol/water solutions, (3)-(7) and (9)-(11) fluoresce weakly in the free state, (8) does not fluoresce and (12) fluoresces strongly. Ultraviolet (UV)- visible spectroscopy shows that (3)-(12) complex to Zn2+, but unlike the remainder, the complexes of (8) and (12) do not fluoresce, with those possessing electron-withdrawing substituents, (4) and (9), being the most fluorescent. On this basis ethyl-2-(2-methyl- quinolyloxy-8-(2,2,2-trifluoroethylsulfonamido)) acetate (19) was prepared and its Zn2+ complex was found to be substantially more fluorescent than that of (2).

  DOI：

  10.1071/ch00134
• 作为产物：
  描述：

  8-amino-6-methoxy-2-methylquinoline 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-(6-hydroxy-2-methyl-8-quinolyl)trifluoroacetamide
  参考文献：
  名称：

  摘要：

  Zinc(II) specific fluorophores are of substantial importance in the study of intracellular Zn2+. Two such widely used fluorophores are 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid, Zinquin (1), and its ethyl ester, Zinquin ester (2), which fluoresce strongly when bound by Zn2+. To gain insight into the factors affecting the fluorescence of such fluorophores the closely related 4-methyl-N-(6-methoxy-2-methyl-8-quinolyl)-benzenesulfonamide (3), and nine analogues (4-12), substituted at sulfur by nine different substituents have been prepared and their fluorescing characteristics and those of their Zn2+ complexes have been examined. The nine substituents are: 2,2,2-trifluoroethyl (4), 4-methoxyphenyl (5), 4-acetamidophenyl (6), 4-bromophenyl (7), 4-nitrophenyl (8), 3-trifluoromethylphenyl (9), naphth-1-yl (10), naphth-2-yl (11) and 5-dimethylaminonaphth-1-yl (12). Under neutral conditions in 75/25% v/v ethanol/water solutions, (3)-(7) and (9)-(11) fluoresce weakly in the free state, (8) does not fluoresce and (12) fluoresces strongly. Ultraviolet (UV)- visible spectroscopy shows that (3)-(12) complex to Zn2+, but unlike the remainder, the complexes of (8) and (12) do not fluoresce, with those possessing electron-withdrawing substituents, (4) and (9), being the most fluorescent. On this basis ethyl-2-(2-methyl- quinolyloxy-8-(2,2,2-trifluoroethylsulfonamido)) acetate (19) was prepared and its Zn2+ complex was found to be substantially more fluorescent than that of (2).

  DOI：

  10.1071/ch00134

文献信息

• ——
  作者：Marc C. Kimber、Indumathy B. Mahadevan、Stephen F. Lincoln、A. David Ward、W. Henry Betts

  DOI：10.1071/ch00134

  日期：——

  Zinc(II) specific fluorophores are of substantial importance in the study of intracellular Zn2+. Two such widely used fluorophores are 2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxyacetic acid, Zinquin (1), and its ethyl ester, Zinquin ester (2), which fluoresce strongly when bound by Zn2+. To gain insight into the factors affecting the fluorescence of such fluorophores the closely related 4-methyl-N-(6-methoxy-2-methyl-8-quinolyl)-benzenesulfonamide (3), and nine analogues (4-12), substituted at sulfur by nine different substituents have been prepared and their fluorescing characteristics and those of their Zn2+ complexes have been examined. The nine substituents are: 2,2,2-trifluoroethyl (4), 4-methoxyphenyl (5), 4-acetamidophenyl (6), 4-bromophenyl (7), 4-nitrophenyl (8), 3-trifluoromethylphenyl (9), naphth-1-yl (10), naphth-2-yl (11) and 5-dimethylaminonaphth-1-yl (12). Under neutral conditions in 75/25% v/v ethanol/water solutions, (3)-(7) and (9)-(11) fluoresce weakly in the free state, (8) does not fluoresce and (12) fluoresces strongly. Ultraviolet (UV)- visible spectroscopy shows that (3)-(12) complex to Zn2+, but unlike the remainder, the complexes of (8) and (12) do not fluoresce, with those possessing electron-withdrawing substituents, (4) and (9), being the most fluorescent. On this basis ethyl-2-(2-methyl- quinolyloxy-8-(2,2,2-trifluoroethylsulfonamido)) acetate (19) was prepared and its Zn2+ complex was found to be substantially more fluorescent than that of (2).