2-hydroxy-N-methyl-3-oxo-N-phenylbutanamide | 1436432-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hydroxy-N-methyl-3-oxo-N-phenylbutanamide
• CAS: 1436432-60-8
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: BCNJMPOKYKCEAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-hydroxy-N-methyl-3-oxo-N-phenylbutanamide 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以83 mg的产率得到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
• 作为产物：
  描述：

  N-甲基-3-氧代-N-苯基丁酰胺 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以92%的产率得到2-hydroxy-N-methyl-3-oxo-N-phenylbutanamide
  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.