5-benzoyl-3-bromo-6-methylpyridin-2(1H)-one | 147293-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoyl-3-bromo-6-methylpyridin-2(1H)-one
• CAS: 147293-46-7
• 化学式: C₁₃H₁₀BrNO₂
• 分子量: 292.132
• InChiKey: BZRPYLXVZQNHGU-UHFFFAOYSA-N

物化性质

• 沸点：
  394.5±42.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  49.93
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-benzoyl-3-bromo-6-methylpyridin-2(1H)-one 在 ammonium acetate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 3-Bromo-2-chloro-5-phenyl-[1,6]naphthyridine
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193
• 作为产物：
  描述：

  5-benzoyl-6-methyl-2(1H)-pyridinone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 8.0h， 以90%的产率得到5-benzoyl-3-bromo-6-methylpyridin-2(1H)-one
  参考文献：
  名称：

  An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones

  摘要：

  Reaction of o-bromo aromatic amines (2, 4, 7, 10, 15) with ethyl potassium xanthate gave the corresponding fused thiazol-2(3H)-thiones (16, 19, 22) which in turn were first alkylated with methyl iodide and then treated with sodium methoxide to produce fused thiazol-2(3H)-ones (18, 21, 24). Treatment of 4-(4-pyridinyl)-benzenamine dihydrobromide (1) with DMSO gave 2-bromo-4-(4-pyridinyl)benzenamine (2). Reduction of 4-(4-bromo-3-nitrophenyl)-pyridine (3) with stannous chloride gave 2-bromo-5-(4-pyridinyl)-benzenamine (4). Treatment of 5-bromo-2-methyl[3,4'-bipyridin]-6(1H)-one (5) with phosphorous oxychloride and ammonia sequentially yielded amino compound (7). Hofmann reaction of 2-chloro-6-methyl-[3,4'-bipyridine]-3-carboxamide resulted in amino compound (10). 5-Acyl-6-methylpyridin-2(1H)-ones (11) were converted to 3-bromo-1,6-naphthyridin-2-amines (15) via a four-step sequence.

  DOI：

  10.3987/com-92-6193