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A kind of aryl-alkyne compound and its preparation method and application

A technology for compounds and synthetic methods, applied in chemical instruments and methods, organic chemistry, instruments, etc., can solve problems such as peripheral nervous system damage, environmental pollution, gold loss, etc., achieving high sensitivity and selectivity, simple detection methods, low cost effect

Inactive Publication Date: 2017-04-12
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The role of gold ions in the treatment of rheumatism is particularly prominent, it can be used as an inhibitor of macrophages and polymorphonuclear leukocytes, but its ion salts (such as hydrochloride) can cause damage to people's liver, kidneys and peripheral nervous system, Therefore, it is potentially toxic to the human body
Moreover, the development and application over the years have resulted in the loss of gold in nature in varying degrees, and also caused environmental pollution.

Method used

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  • A kind of aryl-alkyne compound and its preparation method and application
  • A kind of aryl-alkyne compound and its preparation method and application
  • A kind of aryl-alkyne compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of Aryl-Alkyne Compounds

[0029] The synthesis route of the aryl-alkyne compound (2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-yl 3-phenylpropiolate) of the present invention is:

[0030]

[0031] The synthetic method of aryl-alkyne compound of the present invention is:

[0032] 8-Hydroxyjulolidine (1mmol) and phenylpropiolic acid (1mmol) were dissolved in dichloromethane (10mL), and the resulting mixture was stirred (60min) at 0°C; then the condensing agent EDC (1-( 3-dimethylaminopropyl)-3-ethylcarbodiimide) 1.1mmol and base DMAP (4-dimethylaminopyridine) 0.5mmol, after stirring at room temperature (25°C) for 5 hours, the reaction was stopped, and at room temperature Concentrate by rotary evaporation, the obtained concentrated solution is separated by 300 mesh silica gel column chromatography, and then rinsed with a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:4, and the rinse solution is concentrated under r...

Embodiment 2

[0037] Embodiment 2: Trivalent gold concentration determination

[0038] (1) Establish a trivalent gold detection regression equation

[0039] (1) Prepare a HEPES buffer solution with a pH of 7.4 and a concentration of 10 mM; prepare a 2 mM methanol solution of an aryl-alkyne compound;

[0040] (2) Add 2000 µL HEPES buffer solution and 0.1 µL aryl-alkyne compound methanol solution to a clean fluorescence cuvette at a volume ratio of 20000:1, and detect its fluorescence emission curve ( figure 1 The curve referred to in the probe), which detects the fluorescence intensity value F at 511nm on the fluorescence spectrophotometer 0 =27;

[0041] (3) Add 2000 µL of HEPES buffer solution and 0.1 µL of aryl-alkyne compound methanol solution to another fluorescence cuvette, and then gradually add standard Au 3+ Aqueous solution (Au 3+ The concentration is 2mmol / L), when the accumulatively added standard Au 3+When the volume of the aqueous solution is 2µL, 6µL, 8µL, 14µL, 16µL, 20µ...

Embodiment 3

[0048] Embodiment 3: Anti-interference test

[0049] Prepare a HEPES buffer solution with a pH of 7.4 and a concentration of 10 mM, and prepare a 2 mM solution of aryl-alkyne compound with methanol; add 2 mL of HEPES buffer solution and 0.1 µL of the aryl-alkyne compound in methanol;

[0050] Add no other metal ion solutions to the number 1 cuvette; add 2 molar equivalents of Au to the number 2 cuvette 3+ Aqueous solution, 40 molar equivalents of 19 kinds of common cation aqueous solutions were added to the numbered 3-20 cuvettes (in order of Hg 2+ , Mg 2 + , Ca 2+ 、Cu 2+ , Fe 3+ , Zn 2+ 、Ni 2+ 、 Bi 3+ 、Co 2+ 、Vo 2+ , Mn 2+ 、Ba 2+ 、Cd 2+ , Pb 2+ , Sn 2+ , Yb 3+ 、Cr 3+ , La 3+ 、Er 3+ ), and then put the 20 cuvettes on a fluorescence spectrophotometer to detect their fluorescence intensity values ​​at 511nm, and draw a histogram of the relative fluorescence intensity at 511nm corresponding to different cations, as Figure 4 shown.

[0051] Figure 4 The re...

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Abstract

The invention discloses an aryl-alkyne compound (2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-8-yl 3-phenylpropiolate) as well as preparation and application of the compound. A synthesis method of the aryl-alkyne compound comprises the following steps: under the condition that the temperature is 0 DEG C, dissolving 8-hydroxyjulolidine and phenylpropiolic acid into dichloromethane and adding a condensing agent EDC (Ethylene Dichloride) and an alkali DMAP (Dimethylaminopyridine) and stirring and reacting at 20 to 30 DEG C for 5 to 8 hours; after the reaction, concentrating; carrying out silica-gel column chromatography on concentrated liquid; then eluting, decompressing and evaporating to remove the solvent to obtain a product. The compound can be used as a reagent for detecting the concentration of trivalent gold ions by a fluorescent spectrometry. Firstly, the aryl-alkyne compound provided by the invention has a simple preparation method and low cost and is prepared from the 8-hydroxyjulolidine and the phenylpropiolic acid through a one-step reaction; secondly, the compound can be used as a trivalent gold detection reagent and has high sensitivity and selectivity on Au<3+>; a detection result is not interfered by other metal ions; a detection method is simple and a detection process is carried out in a water phase and can be realized with the help of a fluorescence spectrophotometer.

Description

technical field [0001] The present invention relates to heterocyclic compounds and Au 3+ The detection and analysis technology specifically relates to an aryl-alkyne compound, its preparation method and its application in the detection of trivalent gold ions. Background technique [0002] Gold is a transition metal with special physical and chemical properties. It plays a very important role in many aspects of material science, including catalysis, medicine, food, electronics industry and other manufacturing industries. In recent years, gold and gold Ionic salts are mostly used in medical and chemical fields. Because gold has good biological adaptability, it is also widely used in biology. Gold ions play a particularly prominent role in the treatment of rheumatism. It can be used as an inhibitor of macrophages and polymorphonuclear leukocytes, but its ion salts (such as hydrochloride) can cause damage to people's liver, kidneys and peripheral nervous system. Therefore, it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D455/04C09K11/06G01N21/64
CPCC07D455/04C09K11/06C09K2211/1029G01N21/643
Inventor 李玮杨瑜涛胥稳智徐志栋
Owner HEBEI UNIVERSITY
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