8-nitro-1,2,4-trifluorophenoxazin-3-one | 1451044-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 8-nitro-1,2,4-trifluorophenoxazin-3-one
• 英文别名: 1,2,4-Trifluoro-8-nitrophenoxazin-3-one；1,2,4-trifluoro-8-nitrophenoxazin-3-one
• CAS: 1451044-41-9
• 化学式: C₁₂H₃F₃N₂O₄
• 分子量: 296.162
• InChiKey: XFXRKVBXZUOWLQ-UHFFFAOYSA-N

物化性质

• 熔点：
  212-214 °C
• 沸点：
  336.6±42.0 °C(predicted)
• 密度：
  1.81±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  四氟对苯醌 、 2-氨基-4-硝基苯酚 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以38.5%的产率得到8-nitro-1,2,4-trifluorophenoxazin-3-one
  参考文献：
  名称：

  Synthesis and evaluation of halogenated nitrophenoxazinones as nitroreductase substrates for the detection of pathogenic bacteria

  摘要：

  The synthesis and microbiological evaluation of 7-, 8- and 9-nitro-1,2,4-trihalogenophenoxazin-3-one substrates with potential in the detection of nitroreductase-expressing pathogenic microorganisms are described. The 7- and 9-nitrotrihalogenophenoxazinone substrates were reduced by most Gram-negative microorganisms and were inhibitory to the growth of certain Gram-positive bacteria; however, the majority of Gram-positive strains that were not inhibited by these agents, along with the two yeast strains evaluated, did not reduce the substrates. These observations suggest there are differences in the active site structures and substrate requirements of the nitroreductase enzymes from different strains; such differences may be exploited in the future for differentiation between pathogenic microorganisms. The absence of reduction of the 8-nitrotrihalogenophenoxazinone substrates is rationalized according to their electronic properties and correlates well with previous findings. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.047

文献信息

• Synthesis and evaluation of halogenated nitrophenoxazinones as nitroreductase substrates for the detection of pathogenic bacteria
  作者：Alexandre F. Bedernjak、Paul W. Groundwater、Mark Gray、Arthur L. James、Sylvain Orenga、John D. Perry、Rosaleen J. Anderson

  DOI：10.1016/j.tet.2013.07.047

  日期：2013.9

  The synthesis and microbiological evaluation of 7-, 8- and 9-nitro-1,2,4-trihalogenophenoxazin-3-one substrates with potential in the detection of nitroreductase-expressing pathogenic microorganisms are described. The 7- and 9-nitrotrihalogenophenoxazinone substrates were reduced by most Gram-negative microorganisms and were inhibitory to the growth of certain Gram-positive bacteria; however, the majority of Gram-positive strains that were not inhibited by these agents, along with the two yeast strains evaluated, did not reduce the substrates. These observations suggest there are differences in the active site structures and substrate requirements of the nitroreductase enzymes from different strains; such differences may be exploited in the future for differentiation between pathogenic microorganisms. The absence of reduction of the 8-nitrotrihalogenophenoxazinone substrates is rationalized according to their electronic properties and correlates well with previous findings. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.