4-Hydroxy-3,6-dimethyl-6H-pyrano[3,2-c]quinoline-2,5-dione | 161185-29-1

• 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-Hydroxy-3,6-dimethyl-6H-pyrano[3,2-c]quinoline-2,5-dione
• 英文别名: 4-Hydroxy-3,6-dimethyl-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione；4-hydroxy-3,6-dimethylpyrano[3,2-c]quinoline-2,5-dione
• CAS: 161185-29-1
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: KMIBLEDSSUUNPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-3,6-dimethyl-6H-pyrano[3,2-c]quinoline-2,5-dione 在 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 1.5h， 以97%的产率得到4-Hydroxy-1-methyl-3-propionyl-1H-quinolin-2-one
  参考文献：
  名称：

  Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones

  摘要：

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

  DOI：

  10.1002/prac.19943360707
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 、 甲基丙二酸二乙酯 以 二苯醚 为溶剂， 以64%的产率得到4-Hydroxy-3,6-dimethyl-6H-pyrano[3,2-c]quinoline-2,5-dione
  参考文献：
  名称：

  Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones

  摘要：

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.

  DOI：

  10.1002/prac.19943360707

文献信息

• Syntheses of 3-Acyl-4-hydroxy-2(1H)quinolones
  作者：Thomas Kappe、Rudolf Aigner、Peter Hohengassner、Wolfgang Stadlbauer

  DOI：10.1002/prac.19943360707

  日期：——

  3-Acyl-4-hydroxy-2(1H)-quinolones 5 are obtained by hydrolytic ring opening and subsequent decarboxylation from the corresponding pyrano[3,2-c]quinolin-2,5(6H)-diones 4, which in turn are easily obtained from 1:2 condensation of anilines 1 with diethyl malonate 2a or 1:1 condensation of diethyl alkyl- or arylmalonates 2b-e with 4-hydroxy-2(1H)-quinolones 3. Nitropyranoquinolinediones 6 furnish after ringopening 3-nitroacetyl-4-hydroxy-2(1H)quinolones 8. Pyranoquinolines 7 and 9 with acetyl- or aminosubstituents are hydrolyzed during basic ringopening to yield 5.