6-methyl-2,4-bis(N-(4-methylphenyl)amino)quinoline | 1268471-55-1

• 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-2,4-bis(N-(4-methylphenyl)amino)quinoline
• 英文别名: 6-methyl-2-N,4-N-bis(4-methylphenyl)quinoline-2,4-diamine
• CAS: 1268471-55-1
• 化学式: C₂₄H₂₃N₃
• 分子量: 353.467
• InChiKey: YHIIQNDVIUPGDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酸乙酯 、 6-methyl-2,4-bis(N-(4-methylphenyl)amino)quinoline 在 甲烷磺酸 、 四磷十氧化物 作用下， 以40%的产率得到2,9-dimethyl-7-phenyl-6-(N-(4-methylphenyl)amino)dibenzo[b,h][1,6]naphthyridine
  参考文献：
  名称：

  Efficient Synthetic Route to Access Linear and Angular Dibenzonaphthyridines

  摘要：

  An efficient procedure has been proposed for the synthesis of linear and angular phenyl-substituted dibenzonaphthyridines from anilinoquinolines and benzoic acid in up to 85% yield using Eaton's reagent (a solution of phosphorous pentoxide in methanesulfonic acid) as condensing agent instead of polyphosphoric acid which previously afforded less than 50% yield of the same compounds. Apart from benzoic acid, ethyl benzoate and benzoyl chloride can be used in the synthesis of dibenzonaphthyridines according to the proposed procedure, but the yields are lower.

  DOI：

  10.1134/s1070428019100221
• 作为产物：
  描述：

  2,4-二氯-6-甲基喹啉 、 乙烷,三氯氟- 以 neat (no solvent) 为溶剂， 反应 0.5h， 生成 6-methyl-2,4-bis(N-(4-methylphenyl)amino)quinoline
  参考文献：
  名称：

  Synthesis of Bis-Dibenzonaphthyridines and Evaluation of their Antibacterial Activity

  摘要：

  在多聚磷酸条件下，酞酸与2-甲基-4-N-苯氨基喹啉反应生成6-甲基二苯并[b,h][1,6]萘啶，而相同的反应中，酞酸与2,4-双(N-苯氨基)喹啉则生成二聚二苯并[b,h][1,6]萘啶。为了解释这种意外产物的形成，提出了一种新的反应机制。对多种病原体的抗菌活性筛选证明，与单体类似物相比，二聚体类似物显示出更强的抗菌活性。

  DOI：

  10.13005/ojc/310227

文献信息

• Effect of Substituents in the Syntheses of Phenyl-Substituted Dibenzonaphthyridines
  作者：Manickam Manoj、Karnam Jayaramapillai Rajendra Prasad

  DOI：10.1002/jhet.652

  日期：2013.7

  A facile and elegant syntheses of linear and angular phenyl‐substituted dibenzonaphthyridines from 2,4‐dichloroquinolines through anilinoquinolines have been developed. The substituents in the 4th position of the anilinoquinoline and the temperature were found to play a vital role in the regulation of the yield towards the synthesis of the final compounds. The methyl group in the 7th position of the

  已经开发了一种简便而优美的方法，可从2,4-二氯喹啉到苯胺喹啉合成线性和角苯基取代的二苯并萘啶。发现在苯胺喹啉的第4位上的取代基和温度在最终化合物合成的产率调节中起着至关重要的作用。发现萘啶11-11位的7位上的甲基在空间上阻碍N-甲基化反应，因此比其他衍生物增加了反应时间。
• Synthesis of Bis-Dibenzonaphthyridines and Evaluation of their Antibacterial Activity
  作者：M Sangeetha、M Manoj、R Jayabalan、V Venkateswaran

  DOI：10.13005/ojc/310227

  日期：2015.6.20

  Reaction of phthalic acid with 2-methyl-4-N-phenylaminoquinoline under PPA condition resulted in the formation of 6-methyldibenzo[b,h][1,6]naphthyridines, whereas the same reaction with 2,4-bis(N-phenylamino)quinoline resulted in the dimeric dibenzo[b,h][1,6]naphthyridines. A novel mechanism has been proposed to explain the formation of the unexpected product. Screening for the antibacterial activity against various pathogens, proved that the dimeric analogs showed a better antibacterial activity when compared to their monomeric analogs.

  在多聚磷酸条件下，酞酸与2-甲基-4-N-苯氨基喹啉反应生成6-甲基二苯并[b,h][1,6]萘啶，而相同的反应中，酞酸与2,4-双(N-苯氨基)喹啉则生成二聚二苯并[b,h][1,6]萘啶。为了解释这种意外产物的形成，提出了一种新的反应机制。对多种病原体的抗菌活性筛选证明，与单体类似物相比，二聚体类似物显示出更强的抗菌活性。
• Efficient Synthetic Route to Access Linear and Angular Dibenzonaphthyridines
  作者：M. Sangeetha、M. Manoj

  DOI：10.1134/s1070428019100221

  日期：2019.10

  An efficient procedure has been proposed for the synthesis of linear and angular phenyl-substituted dibenzonaphthyridines from anilinoquinolines and benzoic acid in up to 85% yield using Eaton's reagent (a solution of phosphorous pentoxide in methanesulfonic acid) as condensing agent instead of polyphosphoric acid which previously afforded less than 50% yield of the same compounds. Apart from benzoic acid, ethyl benzoate and benzoyl chloride can be used in the synthesis of dibenzonaphthyridines according to the proposed procedure, but the yields are lower.