3-hydroxy-1,4-dimethylquinolin-2(1H)-one | 93476-41-6

• 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: 3-hydroxy-1,4-dimethylquinolin-2(1H)-one
• 英文别名: 1,4-Dimethyl-3-hydroxy-carbostyril；3-hydroxy-1,4-dimethyl-1H-quinolin-2-one；3-Hydroxy-1,4-dimethylquinolin-2(1H)-one；3-hydroxy-1,4-dimethylquinolin-2-one
• CAS: 93476-41-6
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: DYNHUKPXYPGLNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-甲基-3-氧代-N-苯基丁酰胺 在 硫酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 生成 3-hydroxy-1,4-dimethylquinolin-2(1H)-one
  参考文献：
  名称：

  One-Pot Synthesis of 3-Hydroxyquinolin-2(1H)-ones from N-Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization

  摘要：

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.

  DOI：

  10.1021/jo400541s

文献信息

• One-Pot Synthesis of 3-Hydroxyquinolin-2(1<i>H</i>)-ones from <i>N-</i>Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization
  作者：Yucheng Yuan、Rui Yang、Daisy Zhang-Negrerie、Junwei Wang、Yunfei Du、Kang Zhao

  DOI：10.1021/jo400541s

  日期：2013.6.7

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.