2,3,5-Trimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one | 170996-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 2,3,5-Trimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one
• 英文别名: 2,3,5-Trimethylfuro[3,2-c]pyridine-4-one；2,3,5-trimethylfuro[3,2-c]pyridin-4-one
• CAS: 170996-76-6
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: PYJXPVQYRLRRQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-Dimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以65.5%的产率得到2,3,5-Trimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one
  参考文献：
  名称：

  Synthesis and reactions of 2,3-dimethylfuro[3,2-c]pyridines

  摘要：

  A number of substituted 2,3-dimethylfuro[3,2-c]pyridines was synthesized. 3-(4,5-Dimethyl-2-furyl)propenoic acid (1) was converted to the acid azide 2, which in turn was cyclized to give 2,3-dimethyl-5H-furo [3,2-c]pyridine-4-one (3) by heating at 240 degrees C in Dowtherm. The pyridone 3 was chlorinated with phosphorus oxychloride to give 4, which was reduced with zinc and acetic acid to 2,3-dimethylfuro[3,2-c]pyridine (5). Treatment of 4 with several secondary heterocyclic amines led to compounds 6a-6c. Reaction of pyridone 3 with phosphorus pentasulfide rendered the thione 7, which was methylated to 8a. The 4-methoxy derivative 8b was obtained from 4 with sodium methoxide. 2,3,5-Trimethylfuro[3,2-c]pyridine-4-ones (9) was obtained by reaction of 3 with methyl iodide.

  DOI：

  10.1007/bf00807165

文献信息

• Synthesis and reactions of 2,3-dimethylfuro[3,2-c]pyridines
  作者：V. Bobošík、A. Krutošíková、U. Jordis

  DOI：10.1007/bf00807165

  日期：1995.6

  A number of substituted 2,3-dimethylfuro[3,2-c]pyridines was synthesized. 3-(4,5-Dimethyl-2-furyl)propenoic acid (1) was converted to the acid azide 2, which in turn was cyclized to give 2,3-dimethyl-5H-furo [3,2-c]pyridine-4-one (3) by heating at 240 degrees C in Dowtherm. The pyridone 3 was chlorinated with phosphorus oxychloride to give 4, which was reduced with zinc and acetic acid to 2,3-dimethylfuro[3,2-c]pyridine (5). Treatment of 4 with several secondary heterocyclic amines led to compounds 6a-6c. Reaction of pyridone 3 with phosphorus pentasulfide rendered the thione 7, which was methylated to 8a. The 4-methoxy derivative 8b was obtained from 4 with sodium methoxide. 2,3,5-Trimethylfuro[3,2-c]pyridine-4-ones (9) was obtained by reaction of 3 with methyl iodide.