3,6-dichloro-8-nitroquinoline | 158117-54-5

• 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: 3,6-dichloro-8-nitroquinoline
• 英文别名: 3,6-Dichlor-8-nitro-chinolin
• CAS: 158117-54-5
• 化学式: C₉H₄Cl₂N₂O₂
• 分子量: 243.049
• InChiKey: HZYKVJJNFZDQPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,6-dichloro-8-nitroquinoline 在 盐酸 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以95%的产率得到8-氨基-3,6-二氯喹啉
  参考文献：
  名称：

  Preparation and fungitoxicity of 3,6-dichloro-and 3,6-dibromo-8-quinolinols

  摘要：

  3,6-Dichloro- and 3,6-dibromo-8-quinolinols were prepared by direct halogenation of 8-nitroquinoline by N-halosuccinimide in acetic acid or by halogenation of the corresponding 6-halo-8-nitroquinoline prepared via a Skraup reaction. The nitro group was reduced to amino and the amine was hydrolyzed to the phenol in 70% sulfuric acid at 220-degrees-C. The fungitoxicity of 3,6-dichloro- and 3,6-dibromo-8-quinolinols, as well as intermediates in their preparation, against Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, and Mucor cirinelloides was determined. 3,6-dichloro-8-quinolinol is the most fungitoxic analogue of this class of compounds observed to date.

  DOI：

  10.1007/bf01277632
• 作为产物：
  描述：

  6-氯-8-硝基喹啉 在 N-氯代丁二酰亚胺 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 生成 3,6-dichloro-8-nitroquinoline
  参考文献：
  名称：

  Preparation and fungitoxicity of 3,6-dichloro-and 3,6-dibromo-8-quinolinols

  摘要：

  3,6-Dichloro- and 3,6-dibromo-8-quinolinols were prepared by direct halogenation of 8-nitroquinoline by N-halosuccinimide in acetic acid or by halogenation of the corresponding 6-halo-8-nitroquinoline prepared via a Skraup reaction. The nitro group was reduced to amino and the amine was hydrolyzed to the phenol in 70% sulfuric acid at 220-degrees-C. The fungitoxicity of 3,6-dichloro- and 3,6-dibromo-8-quinolinols, as well as intermediates in their preparation, against Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, and Mucor cirinelloides was determined. 3,6-dichloro-8-quinolinol is the most fungitoxic analogue of this class of compounds observed to date.

  DOI：

  10.1007/bf01277632

文献信息

• SUBSTITUTED 1,10-PHENANTHROLINES. VI. CHLORO DERIVATIVES¹
  作者：FRANCIS H. CASE、SIGMUND CATINO、FRANK SCHOLNICK

  DOI：10.1021/jo01366a006

  日期：1954.1
• Preparation and fungitoxicity of 3,6-dichloro-and 3,6-dibromo-8-quinolinols
  作者：H. Gershon、D. D. Clarke、M. Gershon

  DOI：10.1007/bf01277632

  日期：1994.6

  3,6-Dichloro- and 3,6-dibromo-8-quinolinols were prepared by direct halogenation of 8-nitroquinoline by N-halosuccinimide in acetic acid or by halogenation of the corresponding 6-halo-8-nitroquinoline prepared via a Skraup reaction. The nitro group was reduced to amino and the amine was hydrolyzed to the phenol in 70% sulfuric acid at 220-degrees-C. The fungitoxicity of 3,6-dichloro- and 3,6-dibromo-8-quinolinols, as well as intermediates in their preparation, against Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, and Mucor cirinelloides was determined. 3,6-dichloro-8-quinolinol is the most fungitoxic analogue of this class of compounds observed to date.