1-丁基-4-羟基-3-苯基-1H-喹啉-2-酮 | 144402-89-1

• 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
• 中文名称: 1-丁基-4-羟基-3-苯基-1H-喹啉-2-酮
• 英文名称: 1-Butyl-4-hydroxy-3-phenyl-1H-quinolin-2-one
• 英文别名: 1-butyl-4-hydroxy-3-phenylquinolin-2-one
• CAS: 144402-89-1
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: BITGZPFCMXYHLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-丁基-4-羟基-3-苯基-1H-喹啉-2-酮 在 potassium fluoride 、 磺酰氯 、 18-冠醚-6 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 6.17h， 生成 1-Butyl-3-fluoro-3-phenyl-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：

  methyl 2-(butylamino)benzoate 在 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 12.0h， 生成 1-丁基-4-羟基-3-苯基-1H-喹啉-2-酮
  参考文献：
  名称：

  4-Hydroxy-2-quinolones. 2. Simple synthesis of arboricine

  摘要：

  DOI：

  10.1007/bf00767007

文献信息

• Rapid microwave-enhanced synthesis of 4-hydroxyquinolinones under solvent-free conditions
  作者：Jos H.M Lange、Peter C Verveer、Stefan J.M Osnabrug、Geb M Visser

  DOI：10.1016/s0040-4039(00)02244-9

  日期：2001.2

  potent and selective glycine-site NMDA receptor antagonists of pharmaceutical interest. A novel microwave-enhanced synthesis of such quinolinones under solvent-free conditions has been developed. The quinolinones are easily obtained in a one-pot procedure as a result of the formal amidation of a malonic ester derivative with an aniline and subsequent cyclisation of the intermediate malondianilides

  3-Aryl-4-hydroxyquinolin-2（1 H）-ones是有效的，选择性的，具有药用价值的甘氨酸位点NMDA受体拮抗剂。已经开发了在无溶剂条件下这种喹啉酮的新型微波增强合成方法。由于丙二酸酯衍生物与苯胺的正式酰胺化反应和随后的中间体丙二烯环化反应，可以通过一锅法轻松获得喹啉酮。
• 4-Hydroxy-2-quinolones. 2. Simple synthesis of arboricine
  作者：P. A. Bezuglyi、I. V. Ukrainets、V. I. Treskach、A. V. Turov

  DOI：10.1007/bf00767007

  日期：1992.4
• 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.