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Coumarin derivative and preparation method thereof

A technology of coumarin derivatives and methyl coumarin, which is applied in the field of coumarin derivatives and their preparation, can solve the problems of limited application scope, poor insecticidal effect, poor solubility, etc. Insecticidal effect, good biological activity effect

Active Publication Date: 2015-09-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are many kinds of chemical agents for the prevention and treatment of pine wood nematode at home and abroad, mainly including halogenated hydrocarbons, thioisothiocyanates, macrolides, carbamates, organophosphorus and nicotine, etc. These chemicals have the disadvantages of high toxicity, poor insecticidal effect, and easy residue.
As insecticides, coumarin compounds have the advantages of high efficiency, low toxicity and environmental protection, so they are favored by people. However, most coumarin compounds are derived from plant extracts, the source is limited, and they are soluble in water at room temperature. Poor, which greatly limits its scope of application

Method used

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  • Coumarin derivative and preparation method thereof
  • Coumarin derivative and preparation method thereof
  • Coumarin derivative and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0035] The preparation of embodiment 1 7-hydroxy-4-methylcoumarin

[0036] In a 250ml three-necked flask equipped with a magnetic stirrer, a thermometer and a constant pressure dropping funnel, add resorcinol (11.0g, 100.0mmol) and ethyl acetoacetate (12.6ml, 100.0mmol), stir well until dissolved, and place on ice Cool the water bath to 0°C, slowly add concentrated sulfuric acid (1.0g, 10.2mmol) dropwise, react at 0°C for 30min, then slowly raise the temperature to room temperature and react for 90min, follow the reaction by TLC, and pour the reaction solution into 200.0ml of ice In water, stir the ice-water mixture evenly, let it stand for 10 minutes, vacuum filter to obtain the crude product of 7-hydroxy-4-methylcoumarin, and then recrystallize through industrial alcohol to obtain 16.3g of white needle-shaped product, which is 7-hydroxy-4-methylcoumarin 4-methylcoumarin, yield 92.5%. The qualitative characterization data of gained 7-hydroxyl-4-methylcoumarin is: 1 H-NMR (5...

Embodiment 2

[0037] The preparation of embodiment 2 coumarin derivatives

[0038] Add 7-hydroxy-4-methylcoumarin (1.7g, 10.0mmol) and industrial ethanol (15.0ml) into a 25ml single-necked flask equipped with a magnetic stirrer and stir well at room temperature until dissolved, then add 40.0% methylamine in mass fraction Aqueous solution (1.1ml, 10.0mmol) and 37.5% formaldehyde solution (1.5ml, 20.0mmol) were slowly warmed up to 80°C, refluxed for 5 hours, and the end point of the reaction was determined by TLC. The reaction solvent was removed by rotary evaporation to obtain an oily substance, and water (20.0ml) was added to solidify the oily substance, and then the crude product of yellow coumarin derivative was obtained by suction filtration, washed three times with water (60ml), and then recrystallized through absolute ethanol to obtain 1.9g The light yellow product is the desired coumarin derivative ① with a yield of 82.1%. The structural formula of compound ① is:

[0039]

[0040...

Embodiment 3-9

[0041] The preparation of embodiment 3-9 coumarin derivatives

[0042] Using the same operating steps and the same amount of 7-hydroxyl-4 methylcoumarin, industrial ethanol, formaldehyde and organic primary or secondary amines in Example 2, different types of organic primary or secondary amines, different reaction temperatures and times, to prepare fragrances Soybean derivatives, the experimental data obtained are as shown in table 1:

[0043] Table 1:

[0044]

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Abstract

The invention discloses a coumarin derivative and a preparation method thereof. The coumarin derivative has a structure represented by the formula (I) or (II). The coumarin derivative has higher bioactivity, better insecticidal effect and better solubility in water than coumarin. The preparation method of the coumarin derivative comprises the following steps: 7-hydroxyl-4-methyl coumarin is adopted as a raw material; under the effects of formaldehyde and organic primary amine or organic secondary amine, an amine methylation reaction is carried out, such that the needed coumarin derivative is obtained. The preparation method is simple, the raw materials are cheap and are easy to obtain, and thus the method is suitable for industrialized production. With the product and the method, a problem of limited coumarin extract source is solved. In the formula (I) or (II), R is n-alkyl with a carbon atom number of 1-4.

Description

technical field [0001] The invention relates to a class of coumarin derivatives and a preparation method thereof. Background technique [0002] Coumarin compounds are an important class of organic heterocyclic compounds with natural biological activity. They are widely used in the fields of medicine, life science and chemical industry, and can be used as molecular fluorescent probe agents, antioxidants, anticoagulants, Antibacterial and antibacterial agents, vitamin K antagonists and insecticides are also widely used in the fields of anti-tumor, inhibition of biological enzyme activity and laser pigments. [0003] At present, there are many kinds of chemical agents for the prevention and treatment of pine wood nematode at home and abroad, mainly including halogenated hydrocarbons, thioisothiocyanates, macrolides, carbamates, organophosphorus and nicotine, etc. These chemicals have the disadvantages of high toxicity, poor insecticidal effect, and easy residue. As insecticid...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D311/18A01P7/00
CPCC07D311/18C07D498/04
Inventor 欧睿冠金志敏卓淳淳苗永童耀阳
Owner ZHEJIANG UNIV OF TECH
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