1-ethyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone | 416884-45-2

• 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-ethyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone
• 英文别名: 1'-ethyl-1',4'-dihydro-2,3'-biquinolin-4'-one；1'-ethyl-1',4'-dihydro-2,3'-biquinolyl-4'-one；1'-ethyl-2,3'-biquinolin-4'(1'H)-one；1-ethyl-3-quinolin-2-ylquinolin-4-one
• CAS: 416884-45-2
• 化学式: C₂₀H₁₆N₂O
• 分子量: 300.36
• InChiKey: ADQPRGIBESXCSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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-ethyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone 在 硫酸 、 硝酸 、 溶剂黄146 作用下， 反应 4.5h， 以88%的产率得到1'-ethyl-6'-nitro-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'-Ethyl-1',4'-dihydro-[2,3']biquinolinyl 在 溴 、 sulfur 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 1-ethyl-3-(2-quinolyl)-1,4-dihydro-4-quinolone
  参考文献：
  名称：

  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

  摘要：

  DOI：

  10.1007/s10593-006-0047-9

文献信息

• Investigation of 2,3'-Biquinolyl. 11. Regioselectivity in the Hydroxylation of 1-Alkyl-3-(2-quinolyl)quinolinium Halides
  作者：O. N. Nadelin、A. V. Aksenov

  DOI：10.1023/a:1012403725287

  日期：2001.7
• 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.
• 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
• 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
  作者：A. V. Aksenov、N. V. Demidova、O. P. Demidov、V. I. Goncharov

  DOI：10.1007/s10593-009-0285-8

  日期：2009.4

  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.