2-methyl-4-chloro-5-nitro-8-methoxy quinoline | 18004-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-methyl-4-chloro-5-nitro-8-methoxy quinoline
• 英文别名: 4-chloro-8-methoxy-2-methyl-5-nitroquinoline；4-chloro-8-methoxy-2-methyl-5-nitro-quinoline；4-Chlor-8-methoxy-5-nitro-chinaldin；4-Chloro-8-methoxy-2-methyl-5-nitroquinoline
• CAS: 18004-89-2
• 化学式: C₁₁H₉ClN₂O₃
• 分子量: 252.657
• InChiKey: AGECHHZIPBWVQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-4-chloro-5-nitro-8-methoxy quinoline 在 sodium hydroxide 、 三氯氧磷 、 苯酚 作用下， 反应 28.5h， 生成 2-Methyl-4-(2-methyl-5-nitroimidazol-1-yl)-5-nitroquinolin-8-ol
  参考文献：
  名称：

  Mitra; Pathak, Journal of the Indian Chemical Society, 1982, vol. 59, # 3, p. 367 - 369

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-8-甲氧基-2-甲基喹啉 在 硫酸 、 硝酸 作用下， 反应 12.0h， 以64%的产率得到2-methyl-4-chloro-5-nitro-8-methoxy quinoline
  参考文献：
  名称：

  Synthesis of 6-methoxy-N 2,N 2,N 4,N 4,N 5,N 5-hexamethylquinoline-2,4,5-triamine – a new representative of quinoline proton sponges

  摘要：

  [GRAPHICS]We report the synthesis of 4-chloro-2-methyl-5-nitro-and 2,4-dichloro-5-nitroquinolines, containing methoxy groups at positions 6 and 8. The reaction of these compounds with dimethylamine solution in alcohol was shown to produce not only aminodehalogenation products, but also resulted in nucleophilic substitution of the methoxy groups. The reduction of 6-methoxy-N-2,N-2,N-4,N-4-tetramethyl-5- nitroquinoline-2,4-diamine with subsequent methylation gave 6-methoxy-N-2,N-2,N-4,N-4,N-5,N-5-hexamethylquinoline-2,4,5-triamine, a new representative of quinoline proton sponges.

  DOI：

  10.1007/s10593-015-1693-6

文献信息

• Mitra; Pathak, Journal of the Indian Chemical Society, 1982, vol. 59, # 3, p. 367 - 369
  作者：Mitra、Pathak

  DOI：——

  日期：——
• Synthesis of 6-methoxy-N 2,N 2,N 4,N 4,N 5,N 5-hexamethylquinoline-2,4,5-triamine – a new representative of quinoline proton sponges
  作者：Olga V. Dyablo、Alexander F. Pozharskii、Elena A. Shmoilova、Aleksey O. Savchenko

  DOI：10.1007/s10593-015-1693-6

  日期：2015.3

  [GRAPHICS]We report the synthesis of 4-chloro-2-methyl-5-nitro-and 2,4-dichloro-5-nitroquinolines, containing methoxy groups at positions 6 and 8. The reaction of these compounds with dimethylamine solution in alcohol was shown to produce not only aminodehalogenation products, but also resulted in nucleophilic substitution of the methoxy groups. The reduction of 6-methoxy-N-2,N-2,N-4,N-4-tetramethyl-5- nitroquinoline-2,4-diamine with subsequent methylation gave 6-methoxy-N-2,N-2,N-4,N-4,N-5,N-5-hexamethylquinoline-2,4,5-triamine, a new representative of quinoline proton sponges.