4-(2-chlorophenyl)-6-methoxy-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoline | 1353681-99-8

• 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: 4-(2-chlorophenyl)-6-methoxy-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoline
• 英文别名: 4-(2-Chlorophenyl)-6-methoxy-1-methyl-3-phenylpyrazolo[3,4-b]quinoline；4-(2-chlorophenyl)-6-methoxy-1-methyl-3-phenylpyrazolo[3,4-b]quinoline
• CAS: 1353681-99-8
• 化学式: C₂₄H₁₈ClN₃O
• 分子量: 399.879
• InChiKey: CSXCEOXWNOXXPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chlorophenyl)-6-methoxy-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoline 在 喹啉 、 potassium hydroxide 作用下， 反应 2.0h， 以65%的产率得到10-methoxy-6-methyl-6H-5,6,7-triazadibenzo[f,h]naphtho[3,2,1-cd]azulene
  参考文献：
  名称：

  Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative

  摘要：

  Paper introduces new heteroazulene derivative, 10-methoxy-6-methyl-6H-5,6,7-triazadibenzon[f,h] naphtho[3,2,1-cd]azulene (MMTNA), including chemical aspects of its synthesis likewise optical absorption and fluorescence spectra measured in several organic solvents of different polarity. The obtained experimental results are subjected to the quantum-chemical analysis based on DFT/TDDFT/PCM calculations at the B3LYP/6-31+G(d,p) level of theory. MMTNA demonstrates insignificant solvatochromism of both first absorption and fluorescence bands caused mainly by a weakly polar feature of its ground and lowest excited states. Despite this the emission bands appears to be considerably red shifted with respect to relevant first absorption bands resulting thus to a substantial Stokes shift. Its origin is dominated by the conformational relaxation in the excited state whereas the solvent relaxation has practically no influence on the emission spectra. Low sensitivity to the host environment makes MMTNA dye perspective for a number of applications, particularly in those cases when a high stability of the emission wavelength (color) is demanded. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.07.014
• 作为产物：
  描述：

  2-氯苯甲醛 、 甲氧苯胺 、 1-甲基-3-苯基-1H-吡唑-5(4h)-酮 以 乙二醇 为溶剂， 反应 3.0h， 以38%的产率得到4-(2-chlorophenyl)-6-methoxy-1-methyl-3-phenyl-1H-pyrazolo[3,4-b]quinoline
  参考文献：
  名称：

  Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative

  摘要：

  Paper introduces new heteroazulene derivative, 10-methoxy-6-methyl-6H-5,6,7-triazadibenzon[f,h] naphtho[3,2,1-cd]azulene (MMTNA), including chemical aspects of its synthesis likewise optical absorption and fluorescence spectra measured in several organic solvents of different polarity. The obtained experimental results are subjected to the quantum-chemical analysis based on DFT/TDDFT/PCM calculations at the B3LYP/6-31+G(d,p) level of theory. MMTNA demonstrates insignificant solvatochromism of both first absorption and fluorescence bands caused mainly by a weakly polar feature of its ground and lowest excited states. Despite this the emission bands appears to be considerably red shifted with respect to relevant first absorption bands resulting thus to a substantial Stokes shift. Its origin is dominated by the conformational relaxation in the excited state whereas the solvent relaxation has practically no influence on the emission spectra. Low sensitivity to the host environment makes MMTNA dye perspective for a number of applications, particularly in those cases when a high stability of the emission wavelength (color) is demanded. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.07.014

文献信息

• Synthesis, spectral properties and DFT/TDDFT study on novel methyl heteroazulene derivative
  作者：P. Gąsiorski、K.S. Danel、M. Matusiewicz、T. Uchacz、A.V. Kityk

  DOI：10.1016/j.dyepig.2011.07.014

  日期：2012.4

  Paper introduces new heteroazulene derivative, 10-methoxy-6-methyl-6H-5,6,7-triazadibenzon[f,h] naphtho[3,2,1-cd]azulene (MMTNA), including chemical aspects of its synthesis likewise optical absorption and fluorescence spectra measured in several organic solvents of different polarity. The obtained experimental results are subjected to the quantum-chemical analysis based on DFT/TDDFT/PCM calculations at the B3LYP/6-31+G(d,p) level of theory. MMTNA demonstrates insignificant solvatochromism of both first absorption and fluorescence bands caused mainly by a weakly polar feature of its ground and lowest excited states. Despite this the emission bands appears to be considerably red shifted with respect to relevant first absorption bands resulting thus to a substantial Stokes shift. Its origin is dominated by the conformational relaxation in the excited state whereas the solvent relaxation has practically no influence on the emission spectra. Low sensitivity to the host environment makes MMTNA dye perspective for a number of applications, particularly in those cases when a high stability of the emission wavelength (color) is demanded. (C) 2011 Elsevier Ltd. All rights reserved.