3-acetyl-6-chloro-1-ethyl-4-phenylquinolin-2(1H)-one | 1206210-49-2

• 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: 3-acetyl-6-chloro-1-ethyl-4-phenylquinolin-2(1H)-one
• 英文别名: 3-acetyl-6-chloro-1-ethyl-4-phenylquinolin-2-one
• CAS: 1206210-49-2
• 化学式: C₁₉H₁₆ClNO₂
• 分子量: 325.795
• InChiKey: IMDZFJOYALSDKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-acetyl-6-chloro-1-ethyl-4-phenylquinolin-2(1H)-one 、 N-甲硫脲 在 碘 作用下， 以80.7%的产率得到1-ethyl-3-[2-(methylamino)thiazol-4-yl]-4-phenyl-6-chloroquinolin-2(1H)-one
  参考文献：
  名称：

  Molecular Iodine as a Versatile Reagent for the Synthesis of Thiazoloquinoline—A Potential Antibacterial Agent

  摘要：

  A series of 3-(2-aminothiazol-4-yl) quinolin-2[1H]-ones 3 was prepared by neat reaction of quinolin-2[1H]-ones 1 with thioureas 2 in the presence of molecular iodine. The synthesized compounds were evaluated for their in vitro antimicrobial activities against Escherichia coli, Paedococcus sp., Lactobacillus, Yersinia enterocolitica, and Staphylococcus aureus. The green chemical approach for the synthesis of thiazoloquinolinone 3 was performed under neat conditions using molecular iodine as catalyst as well as reaction medium.

  DOI：

  10.1080/10426507.2010.503209
• 作为产物：
  描述：

  2-氨基-5-氯二苯甲酮 在 Amberlite Na sr1L 作用下， 反应 0.15h， 生成 3-acetyl-6-chloro-1-ethyl-4-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  Solvent-free synthesis and antibacterial studies of some quinolinones

  摘要：

  Solvent-free, microwave-induced condensation of 2-aminoaryl alkyl ketones and ethyl 3-oxobutanoate in the presence of amberlite Na sr1L gave quinolinones in high yield when compared to other catalysts. Further, N-alkylation of the quinolinones was carried out effectively with various halides using amberlite Na sr1L. An N-alkylated quinolinone exhibited enhanced activities against B. subtilis, E. coli, and P. aeruginosa, similar to standard drug ampicillin. Two compounds showed effective activity against S. aureus, and one resulted in moderate activity against E. coli.

  DOI：

  10.1007/s00706-011-0608-1

文献信息

• Solvent-free synthesis and antibacterial studies of some quinolinones
  作者：Radhakrishnan Subashini、Fazlur-Rahman Nawaz Khan

  DOI：10.1007/s00706-011-0608-1

  日期：2012.3

  Solvent-free, microwave-induced condensation of 2-aminoaryl alkyl ketones and ethyl 3-oxobutanoate in the presence of amberlite Na sr1L gave quinolinones in high yield when compared to other catalysts. Further, N-alkylation of the quinolinones was carried out effectively with various halides using amberlite Na sr1L. An N-alkylated quinolinone exhibited enhanced activities against B. subtilis, E. coli, and P. aeruginosa, similar to standard drug ampicillin. Two compounds showed effective activity against S. aureus, and one resulted in moderate activity against E. coli.
• Molecular Iodine as a Versatile Reagent for the Synthesis of Thiazoloquinoline—A Potential Antibacterial Agent
  作者：R. Subashini、F. Nawaz Khan

  DOI：10.1080/10426507.2010.503209

  日期：2011.2.28

  A series of 3-(2-aminothiazol-4-yl) quinolin-2[1H]-ones 3 was prepared by neat reaction of quinolin-2[1H]-ones 1 with thioureas 2 in the presence of molecular iodine. The synthesized compounds were evaluated for their in vitro antimicrobial activities against Escherichia coli, Paedococcus sp., Lactobacillus, Yersinia enterocolitica, and Staphylococcus aureus. The green chemical approach for the synthesis of thiazoloquinolinone 3 was performed under neat conditions using molecular iodine as catalyst as well as reaction medium.