7-trifluoromethyl-4-hydroxy-3-formylquinoline

• 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: 7-trifluoromethyl-4-hydroxy-3-formylquinoline
• 英文别名: 4-Hydroxy-7-(trifluoromethyl)quinoline-3-carbaldehyde；4-oxo-7-(trifluoromethyl)-1H-quinoline-3-carbaldehyde
• 化学式: C₁₁H₆F₃NO₂
• 分子量: 241.169
• InChiKey: QILZHHOBBPPAJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-trifluoromethyl-4-hydroxy-3-formylquinoline 、 1,3,3-三甲基-2-亚甲基吲哚啉 以 乙醇 为溶剂， 反应 3.0h， 以57%的产率得到1,3,3-Trimethyl-8'-(trifluoromethyl)spiro[indole-2,2'-pyrano[3,2-c]quinoline]
  参考文献：
  名称：

  7-Trifluoromethylquinoline-Functionalized Luminescent Photochromic Spiropyran with the Stable Merocyanine Species Both in Solution and in the Solid State

  摘要：

  A new spiropyran (SP2) with the stable merocyanine form (MC2) both in solution and in the solid state at room temperature was designed and synthesized. The stability of MC2 is believed to be due to the electron-withdrawing effect of both the quinoline and the trifluoromethyl groups. H-1 NMR spectra indicate that the ratio of the open form vs the closed form of SP2 is dependent on the polarity of solvents. Single crystals composed of only the open form (MC2) were successfully obtained. X-ray structural analysis indicates that except trifluoromethyl and two methyl groups MC2 is completely planar with an s-trans,s-cis conformation. It should be noted that this is the first report of the X-ray crystal structure of the pure open form of spiropyran. MC2 can be slowly transformed into SP2 at -30degreesC or lower temperature, and the process is accelerated by visible light irradiation. This special photochromic behavior can be explained by the calculated thermodynamic data. The spectral properties of SP2/MC2 in the presence of different metal ions are also studied, and the results show the potential application of SP2/MC2 in sensing metal ions.

  DOI：

  10.1021/jo0487799
• 作为产物：
  描述：

  氯仿 、 7-（三氯甲基）-4-羟基喹啉 在 sodium hydroxide 、 水 作用下， 反应 4.0h， 以16%的产率得到7-trifluoromethyl-4-hydroxy-3-formylquinoline
  参考文献：
  名称：

  7-Trifluoromethylquinoline-Functionalized Luminescent Photochromic Spiropyran with the Stable Merocyanine Species Both in Solution and in the Solid State

  摘要：

  A new spiropyran (SP2) with the stable merocyanine form (MC2) both in solution and in the solid state at room temperature was designed and synthesized. The stability of MC2 is believed to be due to the electron-withdrawing effect of both the quinoline and the trifluoromethyl groups. H-1 NMR spectra indicate that the ratio of the open form vs the closed form of SP2 is dependent on the polarity of solvents. Single crystals composed of only the open form (MC2) were successfully obtained. X-ray structural analysis indicates that except trifluoromethyl and two methyl groups MC2 is completely planar with an s-trans,s-cis conformation. It should be noted that this is the first report of the X-ray crystal structure of the pure open form of spiropyran. MC2 can be slowly transformed into SP2 at -30degreesC or lower temperature, and the process is accelerated by visible light irradiation. This special photochromic behavior can be explained by the calculated thermodynamic data. The spectral properties of SP2/MC2 in the presence of different metal ions are also studied, and the results show the potential application of SP2/MC2 in sensing metal ions.

  DOI：

  10.1021/jo0487799