4-羟基-2,2,4,6-四甲基-1,2,3,4-四氢喹啉 | 258263-74-0

• 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
• 中文名称: 4-羟基-2,2,4,6-四甲基-1,2,3,4-四氢喹啉
• 英文名称: 4-hydroxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline
• 英文别名: 2,2,4,6-tetramethyl-1,3-dihydroquinolin-4-ol
• CAS: 258263-74-0
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: PMAXNNWGIUMOPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.26
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-羟基-2,2,4,6-四甲基-1,2,3,4-四氢喹啉 以 水 为溶剂， 生成 2,2,4,6-四甲基-1H-喹啉
  参考文献：
  名称：

  Photoaddition of water and methanol to 2,2,4,6-tetramethyl-1,2-dihydroquinoline

  摘要：

  Products of the steady-state photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline (1) in water, methanol, and water-ethanol were isolated for the first time and identified by H-1 and C-13 NMR spectroscopy, IR spectroscopy, and mass spectrometry. As a result of the photolysis, the molecule of the solvent is added to the double bond of the heterocycle with formation of 4-hydroxy- (2) or 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline (3) in water and methanol, respectively. Compounds 2 and 3 are converted gradually into 1 in the dark. The rate of the back reaction depends on the solvent and the concentration of the product. Comparison of the products of the photolysis in methanol and hexane at 45 degrees C and of the azoisobutyronitrile-initiated oxidation of 1 at the same temperature has shown that unlike the photolysis in hexane, aminyl radicals are not precursors of the product of the photolysis in methanol. The reaction proceeds via an excited singlet state.

  DOI：

  10.1007/bf02494844
• 作为产物：
  描述：

  2,2,4,6-四甲基-1H-喹啉 在 水 作用下， 以 异丙醇 为溶剂， 以73%的产率得到4-羟基-2,2,4,6-四甲基-1,2,3,4-四氢喹啉
  参考文献：
  名称：

  摘要：

  Steady-state photolysis products of 6- and 8-substituted 2,2,4-trimethyl- 1,2-dihydroquinolines in water and lower alcohols were identified by III NMR. [it the case of electron-donor substituents, the solvent molecule is added to the double bond of the heterocycle affording the corresponding 4-hydroxy- or 4-alkoxytetrahydroquinolines. Nitro-substituted dihydroquinolines are photostable. The addition of EtOH and (PrOH)-O-n occurs only in the presence of water to give a mixture of alkoxy- and hydroxy-adducts. A reaction scheme is suggested.

  DOI：

  10.1023/a:1011369030104

文献信息

• Photoaddition of water and methanol to 2,2,4,6-tetramethyl-1,2-dihydroquinoline
  作者：T. D. Nekipelova、L. N. Kurkovskaya、I. I. Levina、N. A. Klyuev、V. A. Kuzmin

  DOI：10.1007/bf02494844

  日期：1999.11

  Products of the steady-state photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline (1) in water, methanol, and water-ethanol were isolated for the first time and identified by H-1 and C-13 NMR spectroscopy, IR spectroscopy, and mass spectrometry. As a result of the photolysis, the molecule of the solvent is added to the double bond of the heterocycle with formation of 4-hydroxy- (2) or 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline (3) in water and methanol, respectively. Compounds 2 and 3 are converted gradually into 1 in the dark. The rate of the back reaction depends on the solvent and the concentration of the product. Comparison of the products of the photolysis in methanol and hexane at 45 degrees C and of the azoisobutyronitrile-initiated oxidation of 1 at the same temperature has shown that unlike the photolysis in hexane, aminyl radicals are not precursors of the product of the photolysis in methanol. The reaction proceeds via an excited singlet state.
• ——
  作者：T. D. Nekipelova、L. N. Kurkovskaya、I. I. Levina、V. S. Shishkov、V. A. Kuzmin

  DOI：10.1023/a:1011369030104

  日期：——

  Steady-state photolysis products of 6- and 8-substituted 2,2,4-trimethyl- 1,2-dihydroquinolines in water and lower alcohols were identified by III NMR. [it the case of electron-donor substituents, the solvent molecule is added to the double bond of the heterocycle affording the corresponding 4-hydroxy- or 4-alkoxytetrahydroquinolines. Nitro-substituted dihydroquinolines are photostable. The addition of EtOH and (PrOH)-O-n occurs only in the presence of water to give a mixture of alkoxy- and hydroxy-adducts. A reaction scheme is suggested.