3,6-二溴-8-喹啉醇 | 158117-58-9

• 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
• 中文名称: 3,6-二溴-8-喹啉醇
• 英文名称: 3,6-dibromo-8-quinolinol
• 英文别名: 3,6-Dibromoquinolin-8-ol
• CAS: 158117-58-9
• 化学式: C₉H₅Br₂NO
• 分子量: 302.953
• InChiKey: IKRBVJIHPNQEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-二溴-8-喹啉醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 硫酸 为溶剂， 以90%的产率得到3,5,6-tribromo-8-quinolinol
  参考文献：
  名称：

  Preparation and Fungitoxicity of Some Trichloro-, Tribromo-, Tetrachloro-, and Tetrabromo-8-Quinolinols

  摘要：

  3,5,6-, 3,5,7-, 4,5,7-, and 5,6,7-trichloro- and -tribromo-8-quinolinols as well as 3,5,6,7-tetrachloro- and -tetrabromo-8-quinolinols were prepared and tested against six fungi (Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, and Trichophyton mentagrophytes) in Sabouraud dextrose broth. The compounds strongly inhibit five fungi but not M. cirinelloides. They are less active than the related dichloro-8-quinolinols which is attributed to steric hindrance.

  DOI：

  10.1007/s007060170048
• 作为产物：
  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

文献信息

• Preparation and Fungitoxicity of Some Trichloro-, Tribromo-, Tetrachloro-, and Tetrabromo-8-Quinolinols
  作者：Herman Gershon、Donald D. Clarke、Muriel Gershon

  DOI：10.1007/s007060170048

  日期：2001.9

  3,5,6-, 3,5,7-, 4,5,7-, and 5,6,7-trichloro- and -tribromo-8-quinolinols as well as 3,5,6,7-tetrachloro- and -tetrabromo-8-quinolinols were prepared and tested against six fungi (Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, Mucor cirinelloides, and Trichophyton mentagrophytes) in Sabouraud dextrose broth. The compounds strongly inhibit five fungi but not M. cirinelloides. They are less active than the related dichloro-8-quinolinols which is attributed to steric hindrance.
• 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.