3-(3-benzoyloxiranyl)-1H-quinolin-2-one | 1373927-13-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3-benzoyloxiranyl)-1H-quinolin-2-one
• 英文别名: 3-(3-benzoyloxiran-2-yl)-1H-quinolin-2-one
• CAS: 1373927-13-9
• 化学式: C₁₈H₁₃NO₃
• 分子量: 291.306
• InChiKey: NUEFOHKDEXVZHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-benzoyloxiranyl)-1H-quinolin-2-one 在 polyphosphoric acid 作用下， 反应 6.0h， 以57%的产率得到furo[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
• 作为产物：
  描述：

  3-(3-oxo-3-phenylpropenyl)-1H-quinolin-2-one 在 过氧化脲素 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以85%的产率得到3-(3-benzoyloxiranyl)-1H-quinolin-2-one
  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

• Synthesis of 2-Benzoylfuro[2,3-<i>b</i>]Quinolines from Quinoline-Based Chalcones
  作者：Devadoss Karthik Kumar、Subramaniam Parameswaran Rajendran

  DOI：10.1080/00397911.2011.555902

  日期：2012.8.1

  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.