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Tetraphenylethylene borate pyridinium salt, preparation method and application thereof, and reagent and method for detecting fructose

A technology of tetrastyrene boronic acid-based pyridinium salt and styrene boronic acid-based pyridinium salt, which can be applied in chemical instruments and methods, measuring devices, compounds containing elements of Group 3/13 of the periodic table, etc. Poor sensitivity, etc.

Active Publication Date: 2020-07-17
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Currently, methods for detecting fructose in the market such as colorimetry, high performance liquid chromatography and gas chromatography are not suitable for the detection of fructose in complex samples
In recent years, the use of fluorescent probes in the identification of sugar compounds has attracted widespread attention. However, after the probe is combined with fructose, the fluorescence enhancement factor is low, generally less than 60 times, and the sensitivity is poor.

Method used

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  • Tetraphenylethylene borate pyridinium salt, preparation method and application thereof, and reagent and method for detecting fructose
  • Tetraphenylethylene borate pyridinium salt, preparation method and application thereof, and reagent and method for detecting fructose
  • Tetraphenylethylene borate pyridinium salt, preparation method and application thereof, and reagent and method for detecting fructose

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The synthetic route of compound Q1 is as follows:

[0073]

[0074] Synthesis of compound 1-1

[0075] N 2 Under protection, benzophenone (100mg, 0.55mmol) was dissolved in 10mL of anhydrous toluene, carbon tetrabromide (364mg, 1.10mmol) and triphenylphosphine (577mg, 2.20mmol) were added sequentially, and refluxed for 4 days. After cooling to room temperature, the reaction solution was suction-filtered. After suction-filtration, liquid column chromatography (petroleum ether) gave Compound 1-1, 126 mg of white needle-like solid, with a yield of 72%.

[0076] Compound 1-1: 1 H NMR (400MHz, CDCl 3 )δ(ppm):7.36-7.29(m,10H).

[0077] Synthesis of Compound 1-2

[0078] N 2 Under protection, compound 1-1 (100 mg, 0.30 mmol) was dissolved in 4 mL of anhydrous toluene, and 4-pyridineboronic acid (109 mg, 0.89 mmol), tetrakis(triphenylphosphine) palladium (104 mg, 0.09 mmol) and 0.5 mL 2N K 2 CO 3 solution, refluxed for 24 hours. Cool to room temperature, extrac...

Embodiment 2

[0084] The synthetic route of compound Q2 is as follows:

[0085]

[0086] Synthesis of compound 2-1

[0087] N 2 Under protection, 4-bromobenzophenone (10.00g, 38.30mmol) was dissolved in 200mL of anhydrous THF, zinc powder (22.53g, 344.70mmol) was added, and TiCl was added dropwise at -20°C 4 (18.94mL, 172.33mmol), refluxed overnight and cooled to room temperature. Adjust the pH to 7 with 1N HCl, evaporate THF under reduced pressure, extract with dichloromethane, wash the organic phase with water and saturated brine, and anhydrous MgSO 4 Dry, filter with suction, concentrate, and separate by column chromatography (petroleum ether) to obtain compound 2-1, 6.80 g of white solid, with a yield of 72%.

[0088] Compound 2-1: m.p.174-176°C; 1 H NMR (400MHz, CDCl 3 )δ(ppm):7.32-7.28(m,4H),7.20-7.15(m,6H),7.06-7.02(m,4H),6.96-6.91(m,4H).

[0089] Synthesis of compound 2-2a

[0090] N 2 Under protection, compound 2-1 (100mg, 0.20mmol) was dissolved in 2mL THF, and 3-py...

Embodiment 3

[0108] The synthetic routes of compounds Q3 and Q4 are as follows:

[0109]

[0110] Synthesis of Compound 3

[0111] N 2 Under protection, 4,4'-dibromobenzophenone (3.50g, 10.29mmol) was dissolved in 40mL of anhydrous THF, zinc powder (3.36g, 25.73mmol) was added, and TiCl was added dropwise at -20°C 4 (3.00mL, 25.73mmol), refluxed overnight and cooled to room temperature. Adjust the pH to 7 with 1N HCl, evaporate THF under reduced pressure, extract with dichloromethane, wash the organic phase with water and saturated brine respectively, and anhydrous MgSO 4 Drying, suction filtration, concentration, and column chromatography (petroleum ether) gave Compound 3, 3.04 g of a white solid, with a yield of 90%.

[0112] Synthesis of Compound 3-1

[0113] N 2 Under protection, compound 3 (300mg, 0.46mmol) was dissolved in 6mL THF, and 4-pyridineboronic acid (342mg, 2.78mmol), tetrakis(triphenylphosphine) palladium (924mg, 0.8mmol) and 3mL 2N K 2 CO 3 solution, refluxed...

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Abstract

The invention provides tetraphenyl ethylene borate pyridinium salt, a preparation method and application thereof, and a reagent and method for detecting fructose. The structural formula of the tetraphenyl ethylene borate pyridinium is shown as a formula (I) or a formula (II). According to the invention, a series of tetraphenyl ethylene borate pyridinium compounds are prepared by adopting specificraw materials and methods, can be used as fructose detection reagents, have high selectivity and high sensitivity detection capability on fructose, can detect fructose-containing samples including honey, seminal plasma and the like, and have wide application prospects.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a tetraphenylethylene borate pyridinium salt, a preparation method and application, a reagent and a method for detecting fructose. Background technique [0002] Fructose is a monosaccharide that naturally exists in fruits, honey and other foods. It has the advantages of good taste, high sweetness, low glycemic index and not easy to cause dental caries. Therefore, it is widely used in food, beverages and nutritional wines. general purpose sweetener. Similarly, in the field of medicine, crystalline fructose is used to prepare a series of fructose-containing electrolyte injections because of its reduced glycemic index. Fructose is also closely related to human health. For example, fructose in semen provides sperm energy, and its concentration can be used as an indirect measure of testosterone activity. Patients with hereditary fructose intolerance who continue to ingest fructose for a long t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02G01N21/64
CPCC07F5/025G01N21/643G01N2021/6432G01N2021/6439
Inventor 魏超解畅张平竹李小六
Owner HEBEI UNIVERSITY
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