3-hydroxy-1-phenyl-3-propyl-2,4(1H,3H)-quinolinedione | 369651-52-5

• 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-hydroxy-1-phenyl-3-propyl-2,4(1H,3H)-quinolinedione
• 英文别名: 3-Hydroxy-1-phenyl-3-propylquinoline-2,4-dione
• CAS: 369651-52-5
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: DCROWSOMSPGZKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-phenyl-3-propyl-2,4(1H,3H)-quinolinedione 在 氢氧化钾 、 air 作用下， 以 苯 为溶剂， 反应 3.0h， 以73%的产率得到2-hydroxy-1-phenyl-2-propyl-1,2-dihydro-3H-indol-3-one
  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：

  丙基丙二酸二乙酯 在 过氧乙酸 作用下， 生成 3-hydroxy-1-phenyl-3-propyl-2,4(1H,3H)-quinolinedione
  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

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.