4-Methyl-2-quinolone dimer | 136202-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-Methyl-2-quinolone dimer
• 英文别名: (1R,2R,11R,12R)-1,2-dimethyl-9,14-diazapentacyclo[10.8.0.02,11.03,8.015,20]icosa-3,5,7,15,17,19-hexaene-10,13-dione
• CAS: 136202-31-8
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: YBPMIEZLUBDYNF-XAMWDVODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-羟基-4-甲基喹啉 以 乙醇 为溶剂， 反应 5.5h， 以86%的产率得到4-Methyl-2-quinolone dimer
  参考文献：
  名称：

  Lewis acid catalysis of photochemical reactions. 10. Spectroscopy and photochemistry of 2-quinolones and their Lewis acid complexes

  摘要：

  The spectroscopic properties, photodimerization, and cross-cycloaddition reactions of 2-quinolone and three of its methylated derivatives have been investigated in the absence and presence of the strong Lewis acid BF3. Comparison of quinolone, which forms a hydrogen-bonded dimer, and its N-methylated derivatives establishes that hydrogen bonding has little effect on these properties. Methylation at C-4 also has little effect on spectroscopic properties, but does retard photodimerization and result in the formation of photoene products in competition with cycloadduct formation with alkenes. All of the quinolones form strong complexes with BF3. Complex formation results in changes in the NMR, absorption, and fluorescence spectra of the quinolones and in their photochemical behavior. Complexation is proposed to occur on oxygen for all of the quinolones resulting in changes in electron populations that have been probed using GAUSSIAN 86 calculations. A decrease in the energy of the oxygen nonbonding orbitals upon complexation results in a change in the configuration of the lowest singlet state from n,pi* to pi,pi* upon complexation. This change results in an increase in singlet lifetime and a change in cycloaddition mechanism from triplet (stepwise) to singlet (concerted) upon complexation.

  DOI：

  10.1021/jo00018a020