8-amino-3,6-dibromoquinoline | 116632-27-0

• 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: 8-amino-3,6-dibromoquinoline
• 英文别名: 3,6-dibromo-[8]quinolylamine；3,6-Dibrom-[8]chinolylamin；3,6-Dibromoquinolin-8-amine
• CAS: 116632-27-0
• 化学式: C₉H₆Br₂N₂
• 分子量: 301.968
• InChiKey: YNWSMOMPGLSYJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 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：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-amino-3,6-dibromoquinoline 在 硫酸 作用下， 以 水 为溶剂， 反应 8.0h， 以89%的产率得到3,6-二溴-8-喹啉醇
  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：

  8-硝基喹啉 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 铁粉 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 339.0h， 生成 8-amino-3,6-dibromoquinoline
  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. IV. BROMO DERIVATIVES¹
  作者：FRANCIS H. CASE

  DOI：10.1021/jo01146a018

  日期：1951.6
• 3-Haloquinolines with Substituents in the 6- and 8-Positions^1,2
  作者：Robert H. Baker、Samuel W. Tinsley、Dorothy Butler、Byron Riegel

  DOI：10.1021/ja01157a106

  日期：1950.1