(6-methylfuro[2,3-b]quinolin-2-yl)(phenyl)methanone | 1004112-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-methylfuro[2,3-b]quinolin-2-yl)(phenyl)methanone
• 英文别名: (6-Methylfuro[2,3-b]quinolin-2-yl)-phenylmethanone
• CAS: 1004112-04-2
• 化学式: C₁₉H₁₃NO₂
• 分子量: 287.318
• InChiKey: OAMUFIKZSZGCBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,2-二氢-6-甲基-2-氧代喹啉-3-甲醛 在 过氧化脲素 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 (6-methylfuro[2,3-b]quinolin-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of 2-Benzoylfuro[2,3-b]Quinolines from Quinoline-Based Chalcones

  摘要：

  We have described an elegant synthesis of 2-benzoylfuro[2,3-b]quinolines from quinolinyl chalcones via bromination and epoxidation. Interestingly, we found that during the bromination, the chalcones were cyclized to gave monobromodihydrofuroquinolines, which were dehydrobrominated with 1,8-diazabicyclo[5,4,0]undec-7-ene. During the epoxidation, chalcones were not cyclized and gave epoxides, which were treated with polyphosphoric acid to give the title compound. We have differentiated the addition of bromine and urea hydrogen peroxide to alpha,beta-unsaturated carbonyl of quinolinyl chalcones by this new mechanism.

  DOI：

  10.1080/00397911.2011.555902

文献信息

• Microwave-assisted one-pot synthesis of some new furo[2,3-<i>b</i>]quinolines using potassium carbonate under solvent-free conditions
  作者：M Raghavendra、Halehatty S. Bhojya Naik、Bailure S Sherigara

  DOI：10.1139/v07-124

  日期：2007.12.1

  A rapid, solvent-free microwave-assisted method has been developed for the synthesis of novel furo quinolines. The title compounds were achieved by the reaction between corresponding 2-hydroxy-3-formyl-quinolines (1a–1c) with chloroacetamide, ethylchloroacetate, and phenacylbromide in specially designed microwave (MW) oven for organic synthesis in unsealed borosil vessel in presence of potassium carbonate. In this method, isolation is accomplished by just treating the reaction mixture with water, and products were obtained in high yield. Hence, this method was found to be very effective and ecofriendly. The structure of the newly synthesized compounds has been evaluated on the basis of analytical, IR, ¹H NMR, and mass spectral data.Key words: furoquinoline, microwave irradiation, potassium carbonate, solvent-free conditions.

  我们开发了一种快速、无溶剂微波辅助方法来合成新型呋喃喹啉类化合物。相应的 2-羟基-3-甲酰基喹啉（1a-1c）与氯乙酰胺、氯乙酸乙酯和苯酰溴在专门设计的微波（MW）炉中，在碳酸钾存在下，在非密封的硼硅容器中进行有机合成反应，得到了标题化合物。在这种方法中，只需用水处理反应混合物就能完成分离，并能获得高产率的产品。因此，这种方法是非常有效和环保的。根据分析、红外光谱、1H NMR 和质谱数据对新合成化合物的结构进行了评估。