6,7,8,8a-tetrahydro-7,7-dimethyl-1H-quinoline-4,5-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7,8,8a-tetrahydro-7,7-dimethyl-1H-quinoline-4,5-dione
• 英文别名: 7,7-dimethyl-6,8-dihydro-1H-quinoline-4,5-dione
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: PQCHCYHMAYHLIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-[[(5,5-Dimethyl-3-oxocyclohexen-1-yl)amino]methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 600.0 ℃ 、1.33 Pa 条件下， 反应 3.0h， 以83%的产率得到6,7,8,8a-tetrahydro-7,7-dimethyl-1H-quinoline-4,5-dione
  参考文献：
  名称：

  3-Hydroxypyrroles and 1H-pyrrol-3(2H)-ones. Part 13. Reactions of methoxymethylene Meldrum's acid with 3-hydroxypyrroles, with 3-methoxypyrroles and with other active substrates, and pyrolytic heterocyclisations of the products

  摘要：

  Methoxymethylene Meldrum's acid 2 in acetonitrile solution acts as a useful C-electrophile for active substrates such as pyrrole, indole or tertiary enaminones to give substitution products (e.g. 5, 6 or 12, respectively). Primary enaminones react exclusively at the nitrogen atom under these conditions. The effect of ring substituents on the regiochemistry of electrophilic substitution of 3-hydroxypyrroles and 3-methoxypyrroles was studied using methoxymethylene Meldrum's acid as the electrophile. Flash vacuum pyrolysis of the Meldrum's acid derivatives obtained in many of these reactions gave access to a range of heterocyclic systems, including the pyridone 48, quinolinedione 43, benzazepinedione 41 and fused pyrones 50, 52 and 54.

  DOI：

  10.1039/p19930002017