2-(difluoromethyl)-1-phenylquinolin-4(1H)-one | 837364-34-8

• 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: 2-(difluoromethyl)-1-phenylquinolin-4(1H)-one
• 英文别名: 2-Difluoromethyl-1-phenyl-4(1H)-quinolone；2-(difluoromethyl)-1-phenylquinolin-4-one
• CAS: 837364-34-8
• 化学式: C₁₆H₁₁F₂NO
• 分子量: 271.266
• InChiKey: HZMXPTCEHLLUKE-UHFFFAOYSA-N

物化性质

• 熔点：
  210-212 °C(Solv: carbon tetrachloride (56-23-5); toluene (108-88-3))
• 沸点：
  350.9±42.0 °C(Predicted)
• 密度：
  1.296±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(difluoromethyl)-1-phenylquinolin-4(1H)-one 在 盐酸 、 四甲基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.25h， 生成 2-(difluoromethyl)-1-phenyl-2-(trifluoromethyl)-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Nucleophilic trifluoromethylation of RF-containing 4-quinolones, 8-aza- and 1-thiochromones with (trifluoromethyl)trimethylsilane

  摘要：

  Reactions of N-substituted 2-polyfluoroalkyl-4-quinolones and 8-aza-5,7-dimethyl-2-polyfluoroalkylchromones with (trifluoromethyl)-trimethylsilane proceed mainly as a 1,4-nucleophilic trifluoromethylation to give N-substituted 2,2-bis(polyfluoroalkyl)-2,3-dihydroquinolin-4(1H)-ones and 5,7-dimethyl-2,2-bis(polyfluoroalkyl)-2,3-dihydro-4H-pyrano[2,3-b]pyridin-4-ones after acid hydrolysis. Similar reaction with 2-trifluoromethyl-4H-thiochromen-4-one proceeds as a 1,2-addition to give 2,4-bis(trifluoromethyl)-4H-thiochromen-4-yl trimethylsilyl ether. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2005.03.001
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 2-(difluoromethyl)-1-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  A simple and highly efficient synthesis of N-phenyl-2-polyfluoroalkyl-4-quinolones from 2-anilinoacetophenone and RFCO2Et

  摘要：

  The condensation of 2-anilinoacetophenone with RFCO2Et (R-F = CF2H, CF3, C2F5) in the presence of LiH in THF affords the corresponding N-phenyl-2-polyfluoroalkyl-4-quinolones in excellent yields. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.04.010

文献信息

• A simple and highly efficient synthesis of N-phenyl-2-polyfluoroalkyl-4-quinolones from 2-anilinoacetophenone and RFCO2Et
  作者：Boris I. Usachev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.jfluchem.2004.04.010

  日期：2004.9

  The condensation of 2-anilinoacetophenone with RFCO2Et (R-F = CF2H, CF3, C2F5) in the presence of LiH in THF affords the corresponding N-phenyl-2-polyfluoroalkyl-4-quinolones in excellent yields. (C) 2004 Elsevier B.V. All rights reserved.
• Nucleophilic trifluoromethylation of RF-containing 4-quinolones, 8-aza- and 1-thiochromones with (trifluoromethyl)trimethylsilane
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Dmitri V. Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1016/j.jfluchem.2005.03.001

  日期：2005.5

  Reactions of N-substituted 2-polyfluoroalkyl-4-quinolones and 8-aza-5,7-dimethyl-2-polyfluoroalkylchromones with (trifluoromethyl)-trimethylsilane proceed mainly as a 1,4-nucleophilic trifluoromethylation to give N-substituted 2,2-bis(polyfluoroalkyl)-2,3-dihydroquinolin-4(1H)-ones and 5,7-dimethyl-2,2-bis(polyfluoroalkyl)-2,3-dihydro-4H-pyrano[2,3-b]pyridin-4-ones after acid hydrolysis. Similar reaction with 2-trifluoromethyl-4H-thiochromen-4-one proceeds as a 1,2-addition to give 2,4-bis(trifluoromethyl)-4H-thiochromen-4-yl trimethylsilyl ether. (c) 2005 Elsevier B.V. All rights reserved.