3-ethoxycarbonyl-1-methyl-1H-4,5,8-quinolinetrione | 195711-21-8

• 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: 3-ethoxycarbonyl-1-methyl-1H-4,5,8-quinolinetrione
• 英文别名: Marngvmmhksugf-uhfffaoysa-；ethyl 1-methyl-4,5,8-trioxoquinoline-3-carboxylate
• CAS: 195711-21-8
• 化学式: C₁₃H₁₁NO₅
• 分子量: 261.234
• InChiKey: MARNGVMMHKSUGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methacrolein dimethylhydrazone 、 3-ethoxycarbonyl-1-methyl-1H-4,5,8-quinolinetrione 以 四氢呋喃 为溶剂， 以7%的产率得到3-ethoxycarbonyl-1,6-dimethyl-1,8-diazaanthracene-4,5,8-trione
  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：

  2,5-dimethoxy-N-methylaniline 在 ammonium cerium(IV) nitrate 、 三氯氧磷 作用下， 以 氯仿 、 水 、 xylene 为溶剂， 反应 9.17h， 生成 3-ethoxycarbonyl-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

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.

表征谱图