5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-2(1H)-one | 147293-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-2(1H)-one
• 英文别名: 5-acetyl-3-bromo-6-[2-(dimethylamino)ethenyl]-1H-pyridin-2-one
• CAS: 147293-24-1
• 化学式: C₁₁H₁₃BrN₂O₂
• 分子量: 285.14
• InChiKey: IQEVZLDLRUDJPM-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238(dec)°
• 沸点：
  345.2±42.0 °C(Predicted)
• 密度：
  1.542±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-2(1H)-one 在 ammonium acetate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 3-Bromo-2-chloro-5-methyl-[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-乙酰基-6-甲基-2(1H)-吡啶酮 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 反应 13.0h， 生成 5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-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

文献信息

• An Efficient and Novel Synthesis of Fused Thiazol-2(3H)-ones
  作者：Baldev Singh、Patrick O. Pennock、George Y. Lesher、Edward R. Bacon、Donald F. Page

  DOI：10.3987/com-92-6193

  日期：——

  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.