3-Benzyl-1-butyl-3-chloroquinoline-2,4-dione | 144603-30-5

• 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-Benzyl-1-butyl-3-chloroquinoline-2,4-dione
• CAS: 144603-30-5
• 化学式: C₂₀H₂₀ClNO₂
• 分子量: 341.837
• InChiKey: MBKPWPHUWSIVGA-UHFFFAOYSA-N

物化性质

• 沸点：
  539.0±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-Benzyl-1-butyl-3-chloroquinoline-2,4-dione 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以52%的产率得到3-Benzyl-1-butyl-3-fluoro-1H-quinoline-2,4-dione
  参考文献：
  名称：

  Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange

  摘要：

  3-Substituted 4-hydroxy-2(1 H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10. Reaction of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11. Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13. Similarly the dichloro quinolinedione 10 an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.

  DOI：

  10.1007/bf00816857
• 作为产物：
  描述：

  N-丁基苯胺 在 磺酰氯 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.17h， 生成 3-Benzyl-1-butyl-3-chloroquinoline-2,4-dione
  参考文献：
  名称：

  Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange

  摘要：

  3-Substituted 4-hydroxy-2(1 H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10. Reaction of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11. Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13. Similarly the dichloro quinolinedione 10 an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.

  DOI：

  10.1007/bf00816857

文献信息

• Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange
  作者：Wolfgang Stadlbauer、Rita Laschober、Herbert Lutschouig、Gerda Schindler、Thomas Kappe

  DOI：10.1007/bf00816857

  日期：——

  3-Substituted 4-hydroxy-2(1 H)-quinolones 3, 5, 7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones 9 or 10. Reaction of 3, 5, 7 with chloroform gives the dichloromethyl quinolinediones 11. Halogen exchange leads from the chloro quinolinediones 10 to fluoro quinolinedones 12 and to azido quinolinediones 13. Similarly the dichloro quinolinedione 10 an reacts to the difluoro quinolinedione 14, which is reduced to the 3-fluoro-4-hydroxyquinolone 16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione 15.