1-methyl-5,6-dinitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one | 957219-79-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 1-methyl-5,6-dinitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
• 英文别名: 1-Methyl-5,6-dinitro-1,3-dihydro-2h-imidazo-[4,5-b]pyridin-2-one；1-methyl-5,6-dinitro-3H-imidazo[4,5-b]pyridin-2-one
• CAS: 957219-79-3
• 化学式: C₇H₅N₅O₅
• 分子量: 239.147
• InChiKey: SSIBHNRJKZFQAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-methyl-5,6-dinitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 、 硫酸二甲酯 以 sodium hydroxide 为溶剂， 反应 2.5h， 以57%的产率得到1,3-dimethyl-5,6-dinitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮衍生物的硝化

  摘要：

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.

  DOI：

  10.1134/s1070428007030153
• 作为产物：
  描述：

  1-methyl-5-nitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one 在 硫酸 、 potassium nitrate 作用下， 反应 3.0h， 以84%的产率得到1-methyl-5,6-dinitro-1,3-dihydro-imidazo[4,5-b]pyridin-2-one
  参考文献：
  名称：

  1,3-二氢-2H-咪唑并[4,5-b]吡啶-2-酮衍生物的硝化

  摘要：

  Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0-5 degrees C and 60 degrees C gives 5-nitro- and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro- and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5 -nitro compounds. The same products are formed in the nitration of 5,6-dichloro- and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy.

  DOI：

  10.1134/s1070428007030153