5,8-dihydroxy-1-methyl-4(1H)-quinolinone | 195711-18-3

• 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: 5,8-dihydroxy-1-methyl-4(1H)-quinolinone
• 英文别名: 5,8-Dihydroxy-1-methylquinolin-4-one
• CAS: 195711-18-3
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: JDINOGBYHKEQDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,8-dihydroxy-1-methyl-4(1H)-quinolinone 在 manganese(IV) oxide 作用下， 以 水 为溶剂， 反应 0.75h， 以41%的产率得到1-methyl-1H-4,5,8-quinolinetrione
  参考文献：
  名称：

  Hetero Diels-Alder reactions of 4,5,8(1H)-quinolinetriones

  摘要：

  N-substituted 4,5,8(1H)-quinolinetriones react with 1-dimethylamino-1-azadienes giving 1,8-diazaanthracene-4,9,10-triones or 9,10-dihydroxy-1,8-diazaanthracene-4,9,10-triones as the main reaction products. The outcome of the reaction depends on the nature of the N-substituent on the quinone and on the position of substituents on the azadiene. The regioselectivity of the cycloadditions was high, although lower than in the related reactions of 2,5,8(1H)-quinolinetriones previously studied by our group, leading to the isolation of small amounts of 1,5-diazaanthracene-4,9,10-triones. By manipulation of the experimental conditions, the course of the reaction can be diverted to give furo[2,3-f]quinolines through a multi-step, polar [3+2] cycloaddition. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00726-6
• 作为产物：
  描述：

  5,8-dimethoxy-quinolin-4-ol 在 氢氧化钾 、 氢溴酸 作用下， 以 甲醇 、 水 为溶剂， 反应 31.0h， 生成 5,8-dihydroxy-1-methyl-4(1H)-quinolinone
  参考文献：
  名称：

  Hetero Diels-Alder reactions of 4,5,8(1H)-quinolinetriones

  摘要：

  N-substituted 4,5,8(1H)-quinolinetriones react with 1-dimethylamino-1-azadienes giving 1,8-diazaanthracene-4,9,10-triones or 9,10-dihydroxy-1,8-diazaanthracene-4,9,10-triones as the main reaction products. The outcome of the reaction depends on the nature of the N-substituent on the quinone and on the position of substituents on the azadiene. The regioselectivity of the cycloadditions was high, although lower than in the related reactions of 2,5,8(1H)-quinolinetriones previously studied by our group, leading to the isolation of small amounts of 1,5-diazaanthracene-4,9,10-triones. By manipulation of the experimental conditions, the course of the reaction can be diverted to give furo[2,3-f]quinolines through a multi-step, polar [3+2] cycloaddition. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00726-6

文献信息

• Hetero Diels-Alder reactions of 4,5,8(1H)-quinolinetriones
  作者：Madel Mar Blanco、Carmen Avendaño、J.Carlos Menéndez

  DOI：10.1016/s0040-4020(97)00726-6

  日期：1997.8

  N-substituted 4,5,8(1H)-quinolinetriones react with 1-dimethylamino-1-azadienes giving 1,8-diazaanthracene-4,9,10-triones or 9,10-dihydroxy-1,8-diazaanthracene-4,9,10-triones as the main reaction products. The outcome of the reaction depends on the nature of the N-substituent on the quinone and on the position of substituents on the azadiene. The regioselectivity of the cycloadditions was high, although lower than in the related reactions of 2,5,8(1H)-quinolinetriones previously studied by our group, leading to the isolation of small amounts of 1,5-diazaanthracene-4,9,10-triones. By manipulation of the experimental conditions, the course of the reaction can be diverted to give furo[2,3-f]quinolines through a multi-step, polar [3+2] cycloaddition. (C) 1997 Elsevier Science Ltd.