6-methyl-3-(3-oxo-3-phenylpropenyl)-1H-quinolin-2-one | 700359-29-1

• 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: 6-methyl-3-(3-oxo-3-phenylpropenyl)-1H-quinolin-2-one
• CAS: 700359-29-1
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: KLTQWGXMBTXCMS-UHFFFAOYSA-N

物化性质

• 沸点：
  500.2±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.93
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-methyl-3-(3-oxo-3-phenylpropenyl)-1H-quinolin-2-one 在 溴 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 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
• 作为产物：
  描述：

  1,2-二氢-6-甲基-2-氧代喹啉-3-甲醛 、 苯乙酮 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到6-methyl-3-(3-oxo-3-phenylpropenyl)-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, Antitumor, and DNA Binding Behavior of Novel 4-(2-Hydroxyquinolin-3-yl)-6-Phenyl-5, 6 Dihydropyrimidin Derivatives in Aqueous Medium
  作者：Devappa S. Lamani、K. R. Venugopala Reddy、H. S. Bhojya Naik、K. S. R. Pai、Ravishankar Kumar、Fasiulla、H. R. Prakash Naik、L. R. Naik

  DOI：10.1080/15257770.2010.496275

  日期：2010.7.20

  This article deals with the synthesis of 4-(2-hydroxyquinolin-3-yl)-6-phenyl-5,6-dihydropyrimidin derivatives (2a-f), on condensation with various aromatic aldehydes and ketones in aqueous ethanolic NaOH solution yielding the corresponding chalcones (3). These chalcones were further reacted with thiourea/urea in the presence of a base, which led to the formation of the titled derivatives (2a-f). The newly synthesized heterocyles were characterized by elemental analysis, FTIR, 1HNMR, and electronic and mass spectral data. The compounds (2a and 2b) were evulated for in vitro cyctotoxicity against human breast adenocarcinoma cell (MCF-7). In MTT cytotoxicity studies, both quinolinde derivatives were found most effective. The binding interaction behavior of the compound (2a) and (2d) with calf thymus-DNA (CT-DNA) was studied by electronic spectra, viscosity measurements, and thermal denaturation studies. On binding to CT-DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) observed 4.3 x 105 M-1 for (2a), and 3.8 x 105 M-1 for (2d) suggested that compound (2a) binds more strongly with base pairs than (2d).