3-(3,4-dimethoxyphenyl)-1-methylquinolin-4(1H)-one

• 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-(3,4-dimethoxyphenyl)-1-methylquinolin-4(1H)-one
• 英文别名: 3-(3,4-Dimethoxyphenyl)-1-methylquinolin-4-one；3-(3,4-dimethoxyphenyl)-1-methylquinolin-4-one
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: WMRAYKUJQXMSSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-碘喹啉-4-醇 在 potassium phosphate 、 四丁基溴化铵 、 palladium diacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 生成 3-(3,4-dimethoxyphenyl)-1-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1H)-ones by a Reusable and Ligand-Free Suzuki–Miyaura Reaction in Water

  摘要：

  Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki-Miyaura coupling of 1-substituted-3-iodoquinolin-4(1H)-ones with several boronic acids in water using Pd(OAc)(2) as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4(1H)-ones. After a simple workup, the Pd/catalyst-H2O-TBAB system could be reused for at least seven cycles without significant loss of activity.

  DOI：

  10.1021/acs.joc.5b00793

文献信息

• Ohmic Heating-Assisted Synthesis of 3-Arylquinolin-4(1<i>H</i>)-ones by a Reusable and Ligand-Free Suzuki–Miyaura Reaction in Water
  作者：Joana Pinto、Vera L. M. Silva、Ana M. G. Silva、Luís M. N. B. F. Santos、Artur M. S. Silva

  DOI：10.1021/acs.joc.5b00793

  日期：2015.7.2

  Potential bioactive 3-arylquinolin-4(1H)-ones were synthesized under ohmic heating using an efficient, reusable, and ligand-free protocol developed for the Suzuki-Miyaura coupling of 1-substituted-3-iodoquinolin-4(1H)-ones with several boronic acids in water using Pd(OAc)(2) as a catalyst and tetrabutylammonium bromide (TBAB) as the phase transfer catalyst. Good substrate generality, ease of execution, short reaction time, and practicability make this method exploitable for the generation of libraries of B ring-substituted 3-arylquinolin-4(1H)-ones. After a simple workup, the Pd/catalyst-H2O-TBAB system could be reused for at least seven cycles without significant loss of activity.