3-benzyl-1-ethyl-4-hydroxy-2(1H)-quinolone | 144603-05-4

• 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-ethyl-4-hydroxy-2(1H)-quinolone
• 英文别名: 3-Benzyl-1-ethyl-4-hydroxyquinolin-2-one
• CAS: 144603-05-4
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: ZEQHGHSCUUMRBK-UHFFFAOYSA-N

物化性质

• 沸点：
  434.8±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 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：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-1-ethyl-4-hydroxy-2(1H)-quinolone 在 过氧乙酸 、 氢氧化钾 、 air 作用下， 以 苯 为溶剂， 反应 39.0h， 生成 1-乙基-1H-吲哚-2,3-二酮
  参考文献：
  名称：

  Novel Ring Contraction of 3-Hydroxy-2,4(1H,3H)-quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls

  摘要：

  Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.

  DOI：

  10.1021/jo015786d
• 作为产物：
  描述：

  N-乙基苯胺 、 苄基丙二酸二乙酯 反应 4.0h， 以64%的产率得到3-benzyl-1-ethyl-4-hydroxy-2(1H)-quinolone
  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

• Thermal Rearrangement of 3-Hydroxy-1H,3H-quinoline-2,4-diones to 3-Acyloxy-2,3-dihydro-1H-indol-2-ones
  作者：Antonín Klásek、Kamil Koristek、Stanislav Kafka、Janez Kosmrlj

  DOI：10.3987/com-03-9796

  日期：——

  3-Alkyl/aryl-3-hydroxy-1H,3H-quinoline-2,4-diones (2) were transformed into isomeric 3-acyloxy-2,3-dihydro-1H-indol-2-ones (3) by thermally induced molecular rearrangement. All products were characterized by their H-1 NMR, C-13 NMR, and IR spectra.
• Novel Ring Contraction of 3-Hydroxy-2,4(1<i>H</i>,3<i>H</i>)-quinolinediones in Aqueous Alkali. The First Convenient Route to 2-Hydroxyindoxyls
  作者：Stanislav Kafka、Antonín Klásek、Janez Košmrlj

  DOI：10.1021/jo015786d

  日期：2001.9.1

  Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.
• 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.