2,4-dinitro-N-(3-phenyl-2H-chromen-2-ylidene)benzenesulfonamide | 1607814-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dinitro-N-(3-phenyl-2H-chromen-2-ylidene)benzenesulfonamide
• CAS: 1607814-31-2
• 化学式: C₂₁H₁₃N₃O₇S
• 分子量: 451.416
• InChiKey: ZJLRNVPZGAZSQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  145.92
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-dinitro-N-(3-phenyl-2H-chromen-2-ylidene)benzenesulfonamide 、 苯硫酚 以 aq. buffer 为溶剂， 生成 3-phenyl-2H-chromen-2-imine
  参考文献：
  名称：

  Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol

  摘要：

  Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenyisulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pK(aH) values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 x 10(-9) M was also determined for this probe. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.02.001
• 作为产物：
  描述：

  2,4-二硝基苯磺酰氯 、 3-phenyl-2H-chromen-2-imine 以 吡啶 为溶剂， 反应 1.0h， 以35%的产率得到2,4-dinitro-N-(3-phenyl-2H-chromen-2-ylidene)benzenesulfonamide
  参考文献：
  名称：

  Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol

  摘要：

  Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenyisulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pK(aH) values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 x 10(-9) M was also determined for this probe. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.02.001

文献信息

• Three-component one-pot synthesis of N-arylsulfonyl-2-iminocoumarins
  作者：Prashant S. Mandal、A. Vijay Kumar

  DOI：10.1016/j.tet.2018.02.052

  日期：2018.4

  A one-pot, synthesis of N-arylsulfonyl-2-iminocoumarins is developed at ambient temperature by the reaction of 2-hydroxybenzaldehydes, arylacetonitriles, and aryl sulfonyl chlorides using DABCO as a base in a bio-mass-derived green solvent 2-MethylTHF. A simple telescoped process in which 2H-chromen-2-imines are formed in situ by the condensation of 2-hydroxybenzaldehyde and arylacetonitriles. The

  在环境温度下，通过DABCO作为碱，在生物质衍生的绿色溶剂2-MethylTHF中，通过2-羟基苯甲醛，芳基乙腈和芳基磺酰氯的反应，开发出一锅法合成N-芳基磺酰基-2-亚氨基香豆素。 。通过2-羟基苯甲醛和芳基乙腈缩合原位形成2 H-铬-2-亚胺的简单伸缩方法。使形成的亚胺进一步与一锅法中的芳基磺酰氯反应，以获得目标化合物。该方案以实用和环境友好的方式提供了对3-芳基-N-芳基磺酰基-2-亚氨基香豆素的访问，避免了中间合成和纯化的繁琐步骤。