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Preparation and application of fluorescent probe for phiophenol

A fluorescent probe, thiophenol technology, applied in the field of chemical analysis and detection, to achieve the effects of fast response, good selectivity and strong anti-interference ability

Active Publication Date: 2016-10-05
SUZHOU ROWLAND BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the fluorescent probes for thiol compounds are based on the nucleophilicity of thiol for effective recognition. However, due to the similar structure of thiol and fatty thiol, and the stronger nucleophilicity of thiol, many thiol probes The needle cannot distinguish between the two

Method used

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  • Preparation and application of fluorescent probe for phiophenol
  • Preparation and application of fluorescent probe for phiophenol
  • Preparation and application of fluorescent probe for phiophenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of compound 1

[0023] 3-Nitrophthalic anhydride (1.9361g, 10mmol) was dissolved in 20ml of acetic acid, n-butylamine (1.0951g, 15mmol) was slowly added, stirred at room temperature for 10min, heated up, and refluxed at 120°C for 2.5h. After the reaction, cool to room temperature, pour the reaction solution into 50ml of cold water, and after the solid is completely precipitated, filter under reduced pressure, and wash the filter cake with cold water three times (9ml×3) to obtain compound 1 as a white solid. Yield: 2.1252 g. Yield: 85.7%. Compound 1 is characterized as follows: 1 H NMR(500MHz,DMSO):δ H 8.27(d, J=8.1Hz, 1H), 8.16(d, J=7.5Hz, 1H), 8.05(t, J=7.8Hz, 1H), 3.57(t, J=7.1Hz, 2H), 1.55– 1.61(m,2H),1.39–1.20(m,2H),0.90(t,J=7.4Hz,3H). 13 C NMR (126MHz, DMSO)δ C :166.51,163.86,144.63,136.54,134.05,128.62,127.17,123.50,38.13,30.24,19.94,13.94.

Embodiment 2

[0024] Embodiment 2: the synthesis of compound 2

[0025] Compound 1 (0.4964g, 2mmol) obtained in the previous step was dissolved in 15ml of methanol, 10%w / w Pd / C (0.0496g, 5mol%) was added, the system was vacuumed, hydrogen gas was introduced and stirred, and refluxed at 65°C for 12h. After the reaction was terminated, the solid catalyst was removed by suction filtration under reduced pressure, the obtained filtrate was rotary evaporated under reduced pressure to remove the solvent, and compound 2 was obtained by separation by chromatography column. Yield: 0.6240 g. Yield: 71.5%. Compound 2 is characterized as follows: 1H NMR (500MHz, CDCl3) δ7.42(dd, J=8.3,7.1Hz,1H),7.16(d,J=7.6Hz,1H),6.86(d,J=8.8Hz,1H),5.13(s ,1H),3.65(t,J=7.3Hz,2H),1.63–1.70(m,2H),1.35–1.42(m,2H).0.95(t,J=7.4Hz,3H). 13 C NMR (126MHz, DMSO)δ C :170.38,168.77,145.15,135.02,132.86,120.96,112.58,111.38,37.37,30.76,20.09,13.69.

Embodiment 3

[0026] Embodiment 3: the synthesis of compound 3

[0027] Compound 2 obtained in the previous step was dissolved in 10ml of 50% sulfuric acid, stirred under ice-water bath at 0°C, and aqueous sodium nitrite solution (0.0692mg, 1mmol, 2mL of water) was slowly added dropwise. After continuing to stir at 0°C for 30min, the mixture was heated to 90°C and the reaction was continued for 1h. After the reaction, pour the reaction solution into 50ml of water, extract 3 times with ethyl acetate (20mL×3), wash with saturated brine, dry over anhydrous sodium sulfate, remove the solvent by rotary evaporation, and separate by column chromatography after vacuum drying Compound 3. Yield: 0.1862 g. Yield: 85.4%. Compound 3 is characterized as follows: 1 H NMR (500MHz, CDCl3) δ7.70(s, 1H), 7.56(t, J=7.6Hz, 1H), 7.36(d, J=7.2Hz, 1H), 7.15(d, J=8.4Hz, 1H ),3.65(t,J=7.3Hz,2H),1.68–1.62(m,2H),1.40–1.32(m,2H),0.95(t,J=7.4Hz,3H). 13 C NMR (126MHz, DMSO)δ C :170.51,167.91,154.60,136.14,132.11,1...

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Abstract

The invention discloses a novel compound being used in fluorescent detection for phiophenol and particularly relates to a preparation method and an application of a novel fluorescent probe, and belongs to the technical field of chemical analysis and detection. The molecular structural formula of the compound is represented as follows. The fluorescent probe has good selectivity, strong anti-interference capability and high sensitivity, can be used in the fluorescent detection for phiophenol in a biological or environmental sample, and has excellent application prospect.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a preparation method of a novel thiophenol fluorescent probe and the application of the fluorescent probe in detecting thiophenol. Background technique [0002] Thiophenol is widely used in the preparation of intermediates such as medicines and pesticides in organic synthesis. However, thiophenol remaining in water and soil will cause a series of hazards to the environment and human health. Thiophenol can be absorbed by the human body through inhalation, ingestion, or transdermal absorption, which can cause cough, headache, and vomiting. In severe cases, it can cause damage to the human central nervous system, increased heart rate, muscle atrophy, coma and even death. At present, most of the fluorescent probes for thiol compounds are based on the nucleophilicity of thiol groups for effective recognition. However, due to the similar structure of thiol and f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D209/48G01N21/64
Inventor 宋相志高丽刘兴江
Owner SUZHOU ROWLAND BIOTECH
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