N-(1-methylpropyl)-7-(N,N-diethylamino)coumarin-3-carboxamide | 1272593-30-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(1-methylpropyl)-7-(N,N-diethylamino)coumarin-3-carboxamide
• 英文别名: N-butan-2-yl-7-(diethylamino)-2-oxochromene-3-carboxamide
• CAS: 1272593-30-2
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: LBNIXPWLCLPGIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  仲丁胺 、 7-(二乙基氨基)香豆素-3-羧酸 在 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 为溶剂， 反应 18.17h， 以40%的产率得到N-(1-methylpropyl)-7-(N,N-diethylamino)coumarin-3-carboxamide
  参考文献：
  名称：

  Synthesis and spectral characteristics of fluorescent dyes based on coumarin fluorophore and hindered amine stabilizer in solution and polymer matrices

  摘要：

  The spectral properties of novel bifunctional dyes based on - coumarin and diethylamino-coumarin and piperidine parent amine and N-oxyl and N-alkoxy derivatives were compared in cyclohexane, methanol, diethylene glycol, acetonitrile and chloroform solvents and in polystyrene, poly(methyl methacrylate) and poly(vinyl chloride) polymer matrices. The fluorescence of the derivatives excited at the longest-wavelength band around 295 nm is very low for coumarin-based dyes, whereas the fluorescence of the 7-diethylamino-3-carboxy coumarin dyes excited at 420 nm is as intense as that of anthracene in comparable conditions. Intramolecular quenching on the singlet level, monitored by fluorescence and expressed as the ratio of Phi(NH)/Phi(NO) for the parent amine and N-oxyl and Phi(NOR)/Phi(NO) for N-alkyloxy and N-oxyl, is more efficient in polymer matrices than in solvents. The spectral properties of 7-diethylamino-3-carboxy coumarin fluorophores depend on the polarity and viscosity of the environment. Highest values of quantum yield ratio were observed for 7-diethylamino-3-carboxy coumarin dyes in polystyrene and poly(vinylchloride). Though the fluorescence intensity is higher in chloroform or in poly(vinyl chloride) matrices, the intramolecular quenching efficiency of a given fluorophore by nitroxide is higher in low polarity media, such as cyclohexane and polystyrene. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.12.006

文献信息

• Synthesis and spectral characteristics of fluorescent dyes based on coumarin fluorophore and hindered amine stabilizer in solution and polymer matrices
  作者：Martin Danko、Erik Szabo、Pavol Hrdlovic

  DOI：10.1016/j.dyepig.2010.12.006

  日期：2011.8

  The spectral properties of novel bifunctional dyes based on - coumarin and diethylamino-coumarin and piperidine parent amine and N-oxyl and N-alkoxy derivatives were compared in cyclohexane, methanol, diethylene glycol, acetonitrile and chloroform solvents and in polystyrene, poly(methyl methacrylate) and poly(vinyl chloride) polymer matrices. The fluorescence of the derivatives excited at the longest-wavelength band around 295 nm is very low for coumarin-based dyes, whereas the fluorescence of the 7-diethylamino-3-carboxy coumarin dyes excited at 420 nm is as intense as that of anthracene in comparable conditions. Intramolecular quenching on the singlet level, monitored by fluorescence and expressed as the ratio of Phi(NH)/Phi(NO) for the parent amine and N-oxyl and Phi(NOR)/Phi(NO) for N-alkyloxy and N-oxyl, is more efficient in polymer matrices than in solvents. The spectral properties of 7-diethylamino-3-carboxy coumarin fluorophores depend on the polarity and viscosity of the environment. Highest values of quantum yield ratio were observed for 7-diethylamino-3-carboxy coumarin dyes in polystyrene and poly(vinylchloride). Though the fluorescence intensity is higher in chloroform or in poly(vinyl chloride) matrices, the intramolecular quenching efficiency of a given fluorophore by nitroxide is higher in low polarity media, such as cyclohexane and polystyrene. (C) 2011 Elsevier Ltd. All rights reserved.