3-amino-2,6-difluoro-4-nitrophenol | 906081-32-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-amino-2,6-difluoro-4-nitrophenol
• CAS: 906081-32-1
• 化学式: C₆H₄F₂N₂O₃
• 分子量: 190.106
• InChiKey: PIJNDTCKFPAISW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.39
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-amino-2,6-difluoro-4-nitrophenol 在 palladium on activated charcoal 氢气 、 N-氟代双苯磺酰胺 作用下， 以 乙醇 为溶剂， 生成 2-[(4,6-difluoro-5-hydroxy-1H-benzimidazol-2-yl)-difluoromethyl]-N-[2-(4-fluorophenoxy)ethyl]-3-methylbenzimidazole-5-carboxamide
  参考文献：
  名称：

  Identification of metabolites of the tryptase inhibitor CRA-9249: Observation of a metabolite derived from an unexpected hydroxylation pathway

  摘要：

  The metabolites of the tryptase inhibitor CRA-9249 were identified after exposure to liver microsomes. CRA-9249 was found to be degraded rapidly in liver microsomes from rabbit, dog, cynomolgus monkey, and human, and less rapidly in microsomes from rat. The key metabolites included cleavage of an aryl ether, in addition to an unexpected hydroxylation of the amide side chain adjacent to the amide nitrogen. The chemical structures of both metabolites were confirmed by synthesis and comparison to material isolated from the liver microsomes. Several suspected hydroxylated metabolites were also synthesized and analyzed as part of the structure identification process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.003
• 作为产物：
  描述：

  2,3,4-三氟-6-硝基苯胺 在 sodium hydroxide 作用下， 以 various solvent(s) 为溶剂， 以86%的产率得到3-amino-2,6-difluoro-4-nitrophenol
  参考文献：
  名称：

  Identification of metabolites of the tryptase inhibitor CRA-9249: Observation of a metabolite derived from an unexpected hydroxylation pathway

  摘要：

  The metabolites of the tryptase inhibitor CRA-9249 were identified after exposure to liver microsomes. CRA-9249 was found to be degraded rapidly in liver microsomes from rabbit, dog, cynomolgus monkey, and human, and less rapidly in microsomes from rat. The key metabolites included cleavage of an aryl ether, in addition to an unexpected hydroxylation of the amide side chain adjacent to the amide nitrogen. The chemical structures of both metabolites were confirmed by synthesis and comparison to material isolated from the liver microsomes. Several suspected hydroxylated metabolites were also synthesized and analyzed as part of the structure identification process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.003