1-methyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone | 94212-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-methyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone
• 英文别名: 1'-methyl-1',4'-dihydro-2,3'-biquinolin-4'-one；1'-methyl-1',4'-dihydro-2,3'-biquinolyl-4'-one；1'-methyl-[2,3'-biquinolin]-4'(1'H)-one；1'-methyl-1'H-[2,3']biquinolinyl-4'-one；4-Oxo-1-methyl-3--1.4-dihydro-chinolin；1-methyl-3-quinolin-2-ylquinolin-4-one
• CAS: 94212-01-8
• 化学式: C₁₉H₁₄N₂O
• 分子量: 286.333
• InChiKey: XFINKHUKSVVFEM-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: benzene (71-43-2))
• 沸点：
  479.9±45.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone 在 硫酸 、 硝酸 作用下， 反应 0.5h， 以67%的产率得到1'-methyl-5,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-one
  参考文献：
  名称：

  The investigation in 2,3'-biquinoline series 26.* Regioselective nitration of 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones and 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones

  摘要：

  The nitration of 1'-alkyl-1',4'-dihydro-2,3'-biquinolin-4'-ones and 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones has been investigated. It was shown that the regioselectivity of nitration of the first depends on the acidity of the medium and the order of adding reactants. In strongly acidic medium 1'-alkyl-5,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-ones or mixtures of them with 1'-alkyl-5-nitro-1',4'-dihydro-2,3'-biquinolin-4'-ones are formed. In less acidic media 1'-alkyl-6'-nitro-1',4'-dihydro-2,3'-biquinolin-4'-ones and then 1'-alkyl-6,6'-dinitro-1',4'-dihydro-2,3'-biquinolin-4'-ones are formed. Nitration of 1'-alkyl-1',2'-dihydro-2,3'-biquinolin-2'-ones leads to 1'-alkyl-6'-nitro-1',2'-dihydro-2,3'-biquinolin-2'-one and then 1'-alkyl-6,6',8'-trinitro-1',2'-dihydro-2,3'-biquinolin-2'-one.

  DOI：

  10.1007/s10593-009-0285-8
• 作为产物：
  描述：

  1'-methyl-[2,3'-biquinolin]-1'-ium iodide 在 氢氧化钾 、 magnesium(II) perchlorate 、 potassium hexacyanoferrate(III) 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以56.5%的产率得到1-methyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone
  参考文献：
  名称：

  Investigation of 2,3'-Biquinolyl. 11. Regioselectivity in the Hydroxylation of 1-Alkyl-3-(2-quinolyl)quinolinium Halides

  摘要：

  DOI：

  10.1023/a:1012403725287

文献信息

• Synthesis, antibacterial evaluation, and docking studies of azaisoflavone analogues generated by palladium-catalyzed cross coupling
  作者：Yasser M. A. Mohamed、Eirik Johansson Solum、Ahmad F. Eweas

  DOI：10.1007/s00706-018-2252-5

  日期：2018.10

  Palladium-catalyzed, cross-coupling reaction of N-methyl-3-iodo-4-quinolone with boronic acids or N-methyliminodi-acetic acid boronates to obtain azaisoflavone derivatives was investigated through conventional Suzuki Miyuara coupling or by slow release strategy. It has been observed that a slow release approach was a highly successful. In addition, a series of novel azaisoflavones containing alkynyl group were synthesized via Sonogashira reaction. The antibacterial activities of the all synthesized compounds were screened against series of bacterial strains. Furthermore, a molecular docking study was carried out for the most active compounds using Leadit 2.1.8 docking software, and the results were in good agreement with the experimental data. The details of synthetic methods, spectroscopic data, and biological results are reported.[GRAPHICS]
• Investigations on 2,3′-biquinolines. 18. New convenient one-pot synthesis of 1′-alkyl-1′,4′-dihydro-2,3′-biquinolyl-4′-thiones and their conversion into 1′-alkyl-1′,4′-dihydro-2,3′-biquinolyl-4′-ones
  作者：D. V. Moiseev、N. V. Demidova、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-006-0047-9

  日期：2006.1
• Investigations on 2,3′-Biquinoline. 17. Regioselectivity of the Halogenation of 2,3′-Biquinoline Derivatives
  作者：N. V. Demidova、N. Ts. Karaivanov、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-005-0297-y

  日期：2005.9
• Investigations of 2,3′-biquinolines 23. Synthesis of 1′-R-1′,4′-dihydro-2,3′-biquinolin-4′-ones by Claisen condensation
  作者：T. P. Glushenko、V. I. Goncharov、A. V. Aksenov

  DOI：10.1007/s10593-008-0046-0

  日期：2008.3

  A method has been developed for the synthesis of 1'-R-1',4'-dihydro-2,3'-biquinolin-4'-ones based on the interaction of quinaldine with N-alkyl-N-formylanthranilic acid methyl esters under the conditions of the Claisen condensation.