4-chloro-8-fluoro-2-phenylquinoline | 1099705-42-6

• 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: 4-chloro-8-fluoro-2-phenylquinoline
• CAS: 1099705-42-6
• 化学式: C₁₅H₉ClFN
• mdl: MFCD12115076
• 分子量: 257.695
• InChiKey: NKFYVKPVOMAEKD-UHFFFAOYSA-N

物化性质

• 沸点：
  381.9±37.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-8-fluoro-2-phenylquinoline 、 N,N-二甲基甲酰胺 以56%的产率得到8-fluoro-N,N-dimethyl-2-phenylquinolin-4-amine
  参考文献：
  名称：

  Investigation of amination in 4-chloro-2-phenylquinoline derivatives with amide solvents

  摘要：

  Novel 4-amino-2-phenylquinoline derivatives were synthesized by reacting various 4-chloro-2-aryl-quinoline compounds having activated chloro group with the corresponding imide solvents at reflux for overnight. The activity of amination by the amide solvents depended on the competition between the steric and electronic effect of the N-substituents on the amino group. Their activities were shown as N,N-dimethylformamide>N,N-diethylformamide>N-methylformamide>formamide>N,N-dimethylacetamide> N,N-dimethylpropionamide. The yields for the amination products seemed proportional to the ease of the dissociation of the amides. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.09.100
• 作为产物：
  描述：

  8-Fluoro-2-phenyl-1H-quinolin-4-one 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-chloro-8-fluoro-2-phenylquinoline
  参考文献：
  名称：

  Investigation of amination in 4-chloro-2-phenylquinoline derivatives with amide solvents

  摘要：

  Novel 4-amino-2-phenylquinoline derivatives were synthesized by reacting various 4-chloro-2-aryl-quinoline compounds having activated chloro group with the corresponding imide solvents at reflux for overnight. The activity of amination by the amide solvents depended on the competition between the steric and electronic effect of the N-substituents on the amino group. Their activities were shown as N,N-dimethylformamide>N,N-diethylformamide>N-methylformamide>formamide>N,N-dimethylacetamide> N,N-dimethylpropionamide. The yields for the amination products seemed proportional to the ease of the dissociation of the amides. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.09.100

文献信息

• 4-Amino-2-phenylchinoline, Verfahren und Zwischenprodukte zu deren Herstellung sowie diese enthaltende Arzneimittel
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0168812A1

  公开（公告）日：1986-01-22

  Die Verbindungen der Formel worin R' und R2 unabhängig voneinander Wasserstoff oder nieder Alkyl und R3 und R4 unabhängig voneinander Wasserstoff, Halogen oder nieder Alkyl bedeuten, mit der Auflage, dass R3 und R4 nicht gleichzeitig Wasserstoff bedeuten, sind nützlich als Antikonvulsiva und Anxiolytica. Sie können hergestellt werden durch Umsetzung entsprechender 4-Chlor-2-phenylchinoline mit entsprechenden 4-Piperidincarboxamiden oder durch Aminierung von entsprechenden freien Säuren, Säurechloriden oder Estern.

  式中的化合物 其中 R' 和 R2 独立地为氢或低级烷基，R3 和 R4 独立地为氢、卤素或低级烷基，但 R3 和 R4 不能同时为氢。它们可通过相应的 4-氯-2-苯基喹啉与相应的 4-哌啶甲酰胺反应，或通过相应的游离酸、酸氯化物或酯的胺化反应制备。
• Investigation of amination in 4-chloro-2-phenylquinoline derivatives with amide solvents
  作者：Jui-Ying Tsai、Chih-Shiang Chang、Yi-Fan Huang、Hua-Shin Chen、Shao-Kai Lin、Fung Fuh Wong、Li-Jiau Huang、Sheng-Chu Kuo

  DOI：10.1016/j.tet.2008.09.100

  日期：2008.12

  Novel 4-amino-2-phenylquinoline derivatives were synthesized by reacting various 4-chloro-2-aryl-quinoline compounds having activated chloro group with the corresponding imide solvents at reflux for overnight. The activity of amination by the amide solvents depended on the competition between the steric and electronic effect of the N-substituents on the amino group. Their activities were shown as N,N-dimethylformamide>N,N-diethylformamide>N-methylformamide>formamide>N,N-dimethylacetamide> N,N-dimethylpropionamide. The yields for the amination products seemed proportional to the ease of the dissociation of the amides. (C) 2008 Published by Elsevier Ltd.