6-hydroxy-N-methyl-quinaldinium iodide | 797039-83-9

• 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: 6-hydroxy-N-methyl-quinaldinium iodide
• 英文别名: 6-hydroxy-N-methyl-2-quinaldinium iodide；6-Hydroxy-1,2-dimethylquinolin-1-ium iodide；1,2-dimethylquinolin-1-ium-6-ol;iodide
• CAS: 797039-83-9
• 化学式: C₁₁H₁₂NO*I
• 分子量: 301.127
• InChiKey: YYMPCKJYPUTOIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.32
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  24.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-hydroxy-N-methyl-quinaldinium iodide 在 喹啉 作用下， 以 正丁醇 、 苯 为溶剂， 反应 36.0h， 生成 2-[(6-Hydroxy-1-methylquinolin-2-ylidene)methyl]-4-[(6-iodo-1-methylquinolin-1-ium-2-yl)methylidene]-3-oxocyclobuten-1-olate
  参考文献：
  名称：

  Synthesis of Novel Quinaldine-Based Squaraine Dyes:  Effect of Substituents and Role of Electronic Factors

  摘要：

  [GRAPHICS]Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy.

  DOI：

  10.1021/ol048411y
• 作为产物：
  描述：

  对氨基苯酚 在 盐酸 作用下， 反应 18.0h， 生成 6-hydroxy-N-methyl-quinaldinium iodide
  参考文献：
  名称：

  Synthesis of Novel Quinaldine-Based Squaraine Dyes:  Effect of Substituents and Role of Electronic Factors

  摘要：

  [GRAPHICS]Condensation of squaric acid with quinaldinium salts containing electron-donating substituents gave only the semisquaraines. However, with salts possessing electronegative and electron-withdrawing groups, the squaraine dyes were isolated in quantitative yields. The semisquaraines formed undergo condensation with highly nucleophilic salts yielding the unsymmetrical squaraine dyes. These results demonstrate the role of electronic factors and provide valuable information for the design of efficient squaraine-based sensitizers that can have potential applications in photodynamic therapy.

  DOI：

  10.1021/ol048411y

文献信息

• Novel semisquaraine regioisomers: isolation, divergent chemical reactivity and photophysical properties
  作者：Rekha R. Avirah、Kuthanapillil Jyothish、Cherumuttathu H. Suresh、Eringathodi Suresh、Danaboyina Ramaiah

  DOI：10.1039/c1cc15261k

  日期：——

  A zwitterionic semisquaraine 1,3-regioisomer which exhibits distinct photophysical properties and chemical reactivity was isolated. Uniquely, this isomer has been identified as the reactive intermediate in the squaraine dye formation reaction rather than the neutral 1,2-isomer and opens up new avenues for the synthesis of novel dyes for optoelectronic applications.

  一种具有独特光物理特性和化学反应性的两性离子半方形酮1,3-区异构体被分离出来。独特的是，这种异构体被确定为方形染料形成反应中的反应中间体，而非中性1,2-异构体，为新型染料的合成开辟了新的途径，以用于光电应用。
• Synthesis of New Cholesterol- and Sugar-Anchored Squaraine Dyes:  Further Evidence of How Electronic Factors Influence Dye Formation
  作者：Kuthanapillil Jyothish、Rekha R. Avirah、Danaboyina Ramaiah

  DOI：10.1021/ol052639j

  日期：2006.1.1

  Synthesis of new quinaldine-based squaraine dyes linked to cellular recognition elements that exhibit near-infrared absorption (> 740 nm) are described. Both product analysis and theoretical calculations substantiate the interesting electronic effects of various substituents in the dye formation reaction. These results are useful in the synthesis of symmetrical and unsymmetrical squaraine dyes that can have potential biological and photodynamic therapeutical applications.