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Lysine-modified benzofuroxan compound, synthetic method, application and recovery method of lysine-modified benzofuroxan compound as well as method of detecting concentration of copper ions

A technology of lysine modification and benzofurazan, applied in chemical instruments and methods, organic chemistry, measuring devices, etc., can solve the problems of time-consuming, complicated preparation process, high cost, etc., and achieve convenient copper ion concentration and sensitivity High, easy-to-operate effect

Inactive Publication Date: 2015-04-01
SOUTH CHINA NORMAL UNIVERSITY
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Problems solved by technology

However, some of these methods require large sample volumes and complicated preparation procedures, which are time-consuming and costly, and are not conducive to real-time and in situ detection.

Method used

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  • Lysine-modified benzofuroxan compound, synthetic method, application and recovery method of lysine-modified benzofuroxan compound as well as method of detecting concentration of copper ions
  • Lysine-modified benzofuroxan compound, synthetic method, application and recovery method of lysine-modified benzofuroxan compound as well as method of detecting concentration of copper ions
  • Lysine-modified benzofuroxan compound, synthetic method, application and recovery method of lysine-modified benzofuroxan compound as well as method of detecting concentration of copper ions

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preparation example Construction

[0034] The synthetic method of the compound shown in above structural formula, steps are as follows:

[0035] 1) In an ice-salt bath, stir and mix methanol, thionyl chloride, and lysine for 10-20 minutes; then stir and mix at room temperature for 2-4 hours; then reflux at 70-80°C for 30-40 minutes, and cool to At room temperature, remove methanol, add ether to precipitate solid matter, then cool at 0-6°C for 2-4h, precipitate precipitate, filter, and dry to obtain lysine methyl ester hydrochloride;

[0036] 2) Make a solution of lysine methyl ester hydrochloride and mix it with an acid-binding agent, then drop into a solution of 4-chloro-7-nitrobenzofurazan, fully react at room temperature, and monitor the reaction progress by TLC. After the reaction is completed, filter with suction and remove the solvent to obtain a crude product, dissolve the crude product with dichloromethane, wash with water until the water layer is neutral, remove the acid-binding agent, dry the organic ...

Embodiment 1

[0052] Synthesis of 4-lysine-7-nitrobenzofurazan

[0053] The synthetic route of 4-lysine-7-nitrobenzofurazan is as follows:

[0054]

[0055] The structural formula of 4-lysine-7-nitrobenzofurazan is shown in formula I in the synthesis route, and the specific synthesis steps are as follows:

[0056] 1) Add 5.0 ml of anhydrous methanol to a round bottom flask, cool in an ice-salt bath for 5 min, and add 1.0 ml of thionyl chloride dropwise. After the dropwise addition, 1.0 g (6.85 mmol) of lysine solid was added to the above mixed system at one time, and then the system was first stirred in an ice-salt bath for 10.0 min, then stirred at room temperature for 2 h, and then, at 70 Reflux for 30 min under heating in a water bath at -80 °C, then cool to room temperature;

[0057] After evaporating most of the methanol (60-80vol%) in the solution, 40.0 ml of anhydrous ether was added to the system, and a solid substance was precipitated. Then the system was cooled at 4 °C for...

Embodiment 2

[0064] Detection method of copper ion concentration:

[0065] The preparation concentration is 1.0×10 -5 mol / L 4-lysine-7-nitrobenzofurazan solution, adjust the pH to 5.46, add the concentrated solution of copper ions (concentration is 5 mmol / L) dropwise, so that the concentration of copper ions is 0.0, 1.0, 3.0, 5.0, 8.0, 12, 16, 20, 25, 30, 35, 40, 45, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140 μmol / L, to 470 nm is the excitation wavelength, and their fluorescence spectra are measured, and the fluorescence spectra are shown in figure 1 shown. From figure 1 It can be seen that as the concentration of copper ions increases, the intensity of the fluorescence emission peaks gradually weakens.

[0066] Specific detection:

[0067] Detect other metals according to the same steps above, including some heavy metals, alkali metals, alkaline earth metals and transition metals. As a result, these metals do not produce the same phenomenon as copper ions, and the fluorescence inten...

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Abstract

The invention discloses a lysine-modified benzofuroxan compound, a synthetic method, an application and a recovery method of the lysine-modified benzofuroxan compound as well as a method of detecting the concentration of copper ions. The structural formula of the lysine-modified benzofuroxan compound is shown in the specification. The synthetic method of the lysine-modified benzofuroxan compound comprises the following steps: 1) carrying out reaction on methanol, thionyl chloride and lysine to obtain lysine methyl ester hydrochloride; 2) in the presence of an acid binding agent, carrying out reaction on the lysine methyl ester hydrochloride and 4-chlorine-7-nitro-benzofuroxan, and carrying out column chromatography; and 3) dissolving the product obtained in the last step in alkali liquor, extracting for multiple times, regulating a pH value of a water phase, extracting for multiple times, collecting an extractant layer, and carrying out purification. The method of detecting the concentration of the copper ions comprises the following steps: 1) drawing a standard curve; 2) detecting and recording; and 3) carrying out calculation. The recovery method of the lysine-modified benzofuroxan compound comprises the following steps: adding a complexing agent aqueous solution into the compound solution containing the copper ions, uniformly mixing, extracting, collecting an organic phase, and removing a solvent. The lysine-modified benzofuroxan compound is applied to preparing a copper ion fluorescent probe. The synthesized lysine-modified benzofuroxan compound is capable of specifically detecting the copper ions, can be prepared into the probe and can also be recovered.

Description

technical field [0001] The invention relates to a lysine-modified benzofurazan compound, a synthesis method, an application, a recovery method and a method for detecting copper ion concentration. Background technique [0002] On land, copper mainly exists in the form of chloride, hydrate, carbonate, nitrate, and chelate with organic compounds; in aqueous solution, it mainly exists in the form of divalent. Usually the copper content in the environment is relatively low, but it can be enriched through the food chain, so that the content of copper in food can reach quite high. In 1988, the PMTDI (tentative daily intake) value of copper formulated by JECFA was 0.05-0.5 mg / kg bw, and the maximum allowable residual amount of copper in domestic aquatic products was 50 mg / kg. For the human body, divalent copper ions are also essential trace elements, which are widely distributed in the human body, participate in the expression of genes and catalyze reactions of enzymes, and are ver...

Claims

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Application Information

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IPC IPC(8): C07D271/12C09K11/06G01N21/64
CPCC07D271/12C09K11/06C09K2211/1048G01N21/643
Inventor 马立军唐健李煦田叶茂强张敏
Owner SOUTH CHINA NORMAL UNIVERSITY
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