1-methyl-2-(4-fluorophenyl)-3-hydroxy-4(1H)-quinolone | 877667-89-5

• 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: 1-methyl-2-(4-fluorophenyl)-3-hydroxy-4(1H)-quinolone
• 英文别名: 2-(4-Fluorophenyl)-3-hydroxy-1-methylquinolin-4(1H)-one；2-(4-fluorophenyl)-3-hydroxy-1-methylquinolin-4-one
• CAS: 877667-89-5
• 化学式: C₁₆H₁₂FNO₂
• 分子量: 269.275
• InChiKey: PWJKCNVXSMNYHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  吗啉 、 1-methyl-2-(4-fluorophenyl)-3-hydroxy-4(1H)-quinolone 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以76%的产率得到1-methyl-2-(4-(N-morpholinyl)phenyl)-3-hydroxy-4(1H)-quinolone
  参考文献：
  名称：

  Synthesis and fluorescence properties of 2-aryl-3-hydroxyquinolones, a new class of dyes displaying dual fluorescence

  摘要：

  A series of 2-aryl-3-hydroxyquinolones (3HQs) with different electron donating aryl substituents at the position 2 were synthesized. Their absorption and fluorescence properties were studied in solvents of medium and high polarity. Almost all the synthesized 3HQs display dual fluorescence in the tested solvents, in line with an excited state intramolecular proton transfer reaction. For N-methyl substituted compounds, the intensity ratio of the two emission bands was found to be exquisitely sensitive to solvent polarity, with a two orders of magnitude change from toluene to dimethylsulfoxide. Consequently, these compounds appear as prospective polarity fluorescent labels for proteins and nucleic acids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.160
• 作为产物：
  描述：

  4'fluorophenacylanthranilate 在 PPA 作用下， 反应 2.0h， 生成 1-methyl-2-(4-fluorophenyl)-3-hydroxy-4(1H)-quinolone
  参考文献：
  名称：

  2-芳基-3-羟基喹诺酮类，由于激发态分子内质子转移而具有溶剂依赖性双重发射的新型染料

  摘要：

  在此，研究了一系列2-芳基-3-羟基喹诺酮类（3HQs）的荧光性质，并将其与经过充分研究的性质进行了比较。 3-羟基黄酮。发现所有这些化合物在有机物中均显示带良好分隔带的双重荧光溶剂和水溶液。使用稳态和时间分辨荧光光谱，我们证明了它们的双重荧光是由于激发态的分子内质子转移反应。此外，发现大多数测试的3HQ的吸收光谱相似，表明它们对2-芳基环上的取代基不敏感。通过量子化学计算，这与这些分子的非平面性有关，这防止了两个芳族部分之间的共轭。唯一的例外是位置2处带有噻吩环的3HQ衍生物，由于其更平坦的结构，该光谱表现出红移光谱。与之形成鲜明对比的是，发射光谱，尤其是两个发射带的强度比在很大程度上取决于2-芳基环和杂环上的取代基氮。此外，N-甲基取代的3HQ（N–Me 3HQ）表现出很强的溶剂致变色特性，其荧光带强度比随其变化而变化很大。溶剂极性。此外，这些强度比的对数随与2-芳基环中取代基相关的哈

  DOI：

  10.1039/b601400c

文献信息

• 2-Aryl-3-hydroxyquinolones, a new class of dyes with solvent dependent dual emission due to excited state intramolecular proton transfer
  作者：Dmytro A. Yushchenko、Volodymyr V. Shvadchak、Andrey S. Klymchenko、Guy Duportail、Yves Mély、Vasyl G. Pivovarenko

  DOI：10.1039/b601400c

  日期：——

  the fluorescence properties of a series of 2-aryl-3-hydroxyquinolones (3HQs) were investigated and compared with the properties of well-studied 3-hydroxyflavone. All these compounds were found to display dual fluorescence with well-separated bands in organic solvents and aqueous solutions. Using steady-state and time-resolved fluorescence spectroscopy, we showed that their dual fluorescence is due

  在此，研究了一系列2-芳基-3-羟基喹诺酮类（3HQs）的荧光性质，并将其与经过充分研究的性质进行了比较。 3-羟基黄酮。发现所有这些化合物在有机物中均显示带良好分隔带的双重荧光溶剂和水溶液。使用稳态和时间分辨荧光光谱，我们证明了它们的双重荧光是由于激发态的分子内质子转移反应。此外，发现大多数测试的3HQ的吸收光谱相似，表明它们对2-芳基环上的取代基不敏感。通过量子化学计算，这与这些分子的非平面性有关，这防止了两个芳族部分之间的共轭。唯一的例外是位置2处带有噻吩环的3HQ衍生物，由于其更平坦的结构，该光谱表现出红移光谱。与之形成鲜明对比的是，发射光谱，尤其是两个发射带的强度比在很大程度上取决于2-芳基环和杂环上的取代基氮。此外，N-甲基取代的3HQ（N–Me 3HQ）表现出很强的溶剂致变色特性，其荧光带强度比随其变化而变化很大。溶剂极性。此外，这些强度比的对数随与2-芳基环中取代基相关的哈
• Synthesis and fluorescence properties of 2-aryl-3-hydroxyquinolones, a new class of dyes displaying dual fluorescence
  作者：Dmytro A. Yushchenko、Mykhailo D. Bilokin’、Oleksandr V. Pyvovarenko、Guy Duportail、Yves Mély、Vasyl G. Pivovarenko

  DOI：10.1016/j.tetlet.2005.11.160

  日期：2006.2

  A series of 2-aryl-3-hydroxyquinolones (3HQs) with different electron donating aryl substituents at the position 2 were synthesized. Their absorption and fluorescence properties were studied in solvents of medium and high polarity. Almost all the synthesized 3HQs display dual fluorescence in the tested solvents, in line with an excited state intramolecular proton transfer reaction. For N-methyl substituted compounds, the intensity ratio of the two emission bands was found to be exquisitely sensitive to solvent polarity, with a two orders of magnitude change from toluene to dimethylsulfoxide. Consequently, these compounds appear as prospective polarity fluorescent labels for proteins and nucleic acids. (c) 2005 Elsevier Ltd. All rights reserved.