2,3-Dimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one | 170996-75-5

• 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-Dimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one
• 英文别名: 2,3-Dimethylfuro[3,2-c]pyridin-4(5H)-one；2,3-dimethyl-5H-furo[3,2-c]pyridin-4-one
• CAS: 170996-75-5
• 化学式: C₉H₉NO₂
• mdl: MFCD04122069
• 分子量: 163.176
• InChiKey: WYJVXOSPQJITJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-Dimethyl-4,5-dihydrofuro<3,2-c>pyridin-4-one 在 三氯氧磷 作用下， 反应 4.0h， 以82.9%的产率得到4-Chloro-2,3-dimethylfuro<3,2-c>pyridine
  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
• 作为产物：
  描述：

  E-3-(4,5-Dimethyl-2-furyl)propenoic azide 在 diphenyl ether-biphenyl eutectic 、 三正丁胺 作用下， 以 甲苯 为溶剂， 以53.9%的产率得到2,3-Dimethyl-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.