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Macrocyclic compound and synthetic method thereof and application

A technology of macrocyclic compounds and synthetic methods, which is applied in the field of synthesis of macrocyclic compounds, and can solve problems such as water resource pollution, unstable free radicals, and expensive instruments

Active Publication Date: 2017-01-04
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, paraquat has a strong adsorption effect in the soil and produces residues in the soil, which seriously pollutes water resources, is extremely toxic to humans and animals, and has no specific antidote. Therefore, a safe, fast and efficient detection of paraquat is established. methodological research has received extensive attention
[0004] At present, the detection methods of paraquat mainly include gas chromatography, high performance liquid chromatography, and spectrophotometer. However, the detection of paraquat by gas chromatography is complicated and requires well-trained operators, which is not suitable for the detection of large quantities of samples. , and its detection limit is 20 μg / L; high-performance liquid chromatography has complex sample pretreatment and expensive instruments, and is also not suitable for rapid detection of large batches of samples, while spectrophotometry has the characteristics of rapid detection and simple operation. , but the free radicals produced by its color development are very unstable, which affects the accuracy of the results, and its detection limit is too high, so it cannot meet the trace detection of paraquat, and its detection limit is 0.15mg / L

Method used

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  • Macrocyclic compound and synthetic method thereof and application
  • Macrocyclic compound and synthetic method thereof and application
  • Macrocyclic compound and synthetic method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A macrocyclic compound, the chemical formula of the macrocyclic compound is C 60 h 60 N 12 o 6 , whose structural formula is:

[0036]

[0037] The synthetic method of described macrocyclic compound is synthesized according to the following steps:

[0038] (1) 2-hydroxybenzimidazole (2g, 0.015mol), tetrabutylammonium bromide (0.24g, 0.75mmol), toluene 50mL, 40% sodium hydroxide solution 20mL and iodomethane (2mL, 0.032mol) , heated at 60-80°C for 19 hours to obtain product A;

[0039] (2) Mix product A, hydrochloric acid solution and formic acid to obtain product B;

[0040] (3) adding concentration to product B is 40% formaldehyde solution, stir evenly, obtain product C;

[0041](4) Product C was stirred at room temperature for 5 hours, a white precipitate appeared, and product D was obtained;

[0042] (5) Product D was filtered by suction, washed with methanol and dichloromethane successively, and dried to obtain a white solid.

[0043] Described hydrochlor...

Embodiment 2

[0045] A macrocyclic compound, the chemical formula of the macrocyclic compound is C 60 h 60 N 12 o 6 , whose structural formula is:

[0046]

[0047] The synthetic method of described macrocyclic compound is synthesized according to the following steps:

[0048] (1) 2-hydroxybenzimidazole (2g, 0.015mol), tetrabutylammonium bromide (0.24g, 0.75mmol), toluene 50mL, 40% sodium hydroxide solution 20mL and iodomethane (2mL, 0.032mol) , heated at 60-80°C for 19 hours to obtain product A;

[0049] (2) Add hydrochloric acid solution and formic acid to product A, mix well to obtain product B;

[0050] (3) adding concentration to product B is the formaldehyde solution of 50%, stirs evenly, obtains product C;

[0051] (4) Product C was stirred at room temperature for 6 hours, a white precipitate appeared, and product D was obtained;

[0052] (5) Product D was filtered by suction, washed with methanol and dichloromethane successively, and dried to obtain a white solid.

[0053...

Embodiment 3

[0055] A macrocyclic compound, the chemical formula of the macrocyclic compound is C 60 h 60 N 12 o 6 , whose structural formula is:

[0056]

[0057] The synthetic method of described macrocyclic compound is synthesized according to the following steps:

[0058] (1) 2-hydroxybenzimidazole (2g, 0.015mol), tetrabutylammonium bromide (0.24g, 0.75mmol), toluene 50mL, 40% sodium hydroxide solution 20mL and iodomethane (2mL, 0.032mol) , heated at 60-80°C for 19 hours to obtain product A;

[0059] (2) Add hydrochloric acid solution and formic acid to product A, after mixing, get product B;

[0060] (3) adding a concentration of 30% formaldehyde solution to product B, stirring evenly, to obtain product C;

[0061] (4) Product C was stirred at room temperature for 4 hours, a white precipitate appeared, and product D was obtained;

[0062] (5) Product D was filtered by suction, washed with methanol and dichloromethane successively, and dried to obtain a white solid.

[0063]...

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Abstract

The invention discloses a macrocyclic compound and a synthetic method thereof. The method for synthesizing the macrocyclic compound is simple, consumption time is short, and the yield is high and can reach 75% or above. The macrocyclic compound has a conjugated structure and can generate fluorescence under excitation of ultraviolet light and have good optical response properties, and a new development direction is provided for research and application of macrocyclic chemistry and host-guest chemistry. The macrocyclic compound can detect paraquat in mixed solution of dichloromethane and methanol and have the advantages of being low in cost, quick in detection speed and high in efficiency and the like.

Description

technical field [0001] The invention relates to a macrocyclic compound and a synthesis method thereof, in particular to a synthesis method of a macrocyclic compound with high yield and good optical properties. Background technique [0002] In recent years, macrocyclic chemistry has developed vigorously, and many macrocyclic compounds with attractive structures and novel properties emerge in an endless stream, such as various crown ethers, cyclodextrins, calixarenes, pillar arenes, cycloarenes, porphyrins, and macrocyclic lactones. , Cyclopeptide, cyclofan, corrole, melon ring, cyclic Schiff base, macrocyclic polyamine and other macrocyclic synthetic substances, as well as natural biological macrocyclic compounds isolated from soil bacteria and marine organisms. Macrocyclic host molecules are constantly being enriched in terms of metal coordination, supramolecular self-assembly, host-guest chemistry, etc., and the intersection of supramolecular chemistry and other disciplines...

Claims

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Application Information

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IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC07D487/22C09K11/06C09K2211/1044G01N21/643G01N2021/6443
Inventor 丛航陈曼王方
Owner GUIZHOU UNIV
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