7-(N'-butylureido)-1-methyl-3H-phenoxazin-3-one | 834897-44-8

• 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: 7-(N'-butylureido)-1-methyl-3H-phenoxazin-3-one
• 英文别名: Urea, N-butyl-N'-(1-methyl-3-oxo-3H-phenoxazin-7-yl)-；1-butyl-3-(9-methyl-7-oxophenoxazin-3-yl)urea
• CAS: 834897-44-8
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: GLCDGYCHERXKBN-UHFFFAOYSA-N

物化性质

• 沸点：
  462.9±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  79.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-amino-1-methyl-3H-phenoxazin-3-one 、 异氰酸正丁酯 以 吡啶 为溶剂， 反应 6.0h， 以55%的产率得到7-(N'-butylureido)-1-methyl-3H-phenoxazin-3-one
  参考文献：
  名称：

  Rational Design of a Chromo- and Fluorogenic Hybrid Chemosensor Material for the Detection of Long-Chain Carboxylates

  摘要：

  A strategy for the rational design of a new optical sensor material for the selective recognition of long-chain carboxylates in water is presented. The approach relies on the combination of structure-property relationships to single out the optimal molecular sensor unit and the tuning of the sensing characteristics of an inorganic support material. A spacer-substituted 7-urea-phenoxazin-3-one was employed as the signaling moiety and a mesoporous trimethylsilylated UVM-7 (MCM-41 type) material served as the solid support. The sensor material shows the advantageous features of both modules that is absorption and emission in the visible spectral range, a fluorescence red-shift and enhancement upon analyte coordination, and the amplification of noncovalent (binding) and hydrogen -bonding (recognition) interactions in the detection event. Besides these basic results that are related to the design and performance of the sensor material, the paper discusses general aspects of amido-substituted phenoxazinone photophysics and addresses some general features of molecular anion recognition chemistry in aqueous vs nonaqueous media, utilizing steady-state and time-resolved optical as well as NMR spectroscopies. Detailed studies on potentially competing biochemical species and a first access to the schematic model of the response of the sensor material as obtained by a combination of fluorescence lifetime distribution analysis and Langmuir-type fitting of the gross binding constants complement the key issues of the paper.

  DOI：

  10.1021/ja045683n

文献信息

• Rational Design of a Chromo- and Fluorogenic Hybrid Chemosensor Material for the Detection of Long-Chain Carboxylates
  作者：Ana B. Descalzo、Knut Rurack、Hardy Weisshoff、Ramón Martínez-Máñez、M. Dolores Marcos、Pedro Amorós、Katrin Hoffmann、Juan Soto

  DOI：10.1021/ja045683n

  日期：2005.1.1

  A strategy for the rational design of a new optical sensor material for the selective recognition of long-chain carboxylates in water is presented. The approach relies on the combination of structure-property relationships to single out the optimal molecular sensor unit and the tuning of the sensing characteristics of an inorganic support material. A spacer-substituted 7-urea-phenoxazin-3-one was employed as the signaling moiety and a mesoporous trimethylsilylated UVM-7 (MCM-41 type) material served as the solid support. The sensor material shows the advantageous features of both modules that is absorption and emission in the visible spectral range, a fluorescence red-shift and enhancement upon analyte coordination, and the amplification of noncovalent (binding) and hydrogen -bonding (recognition) interactions in the detection event. Besides these basic results that are related to the design and performance of the sensor material, the paper discusses general aspects of amido-substituted phenoxazinone photophysics and addresses some general features of molecular anion recognition chemistry in aqueous vs nonaqueous media, utilizing steady-state and time-resolved optical as well as NMR spectroscopies. Detailed studies on potentially competing biochemical species and a first access to the schematic model of the response of the sensor material as obtained by a combination of fluorescence lifetime distribution analysis and Langmuir-type fitting of the gross binding constants complement the key issues of the paper.