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

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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

Method used

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

Examples

Experimental program
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Effect test

Example Embodiment

[0035] Example 1 Preparation of 7-hydroxy-4-methylcoumarin

[0036] In a 250ml three-necked flask equipped with magnetic stirring, thermometer and constant pressure dropping funnel, add resorcinol (11.0g, 100.0mmol) and ethyl acetoacetate (12.6ml, 100.0mmol), stir well to dissolve, ice The temperature of the water bath was lowered to 0°C, concentrated sulfuric acid (1.0g, 10.2mmol) was slowly added dropwise, and after reacting at 0°C for 30 minutes, the temperature was slowly raised to room temperature and the reaction was reacted for 90 minutes. TLC followed the reaction. After the reaction, the reaction solution was poured into 200.0ml ice Stir the ice-water mixture uniformly in water, let it stand for 10 min, and vacuum filter to obtain crude 7-hydroxy-4-methylcoumarin, which is recrystallized with industrial alcohol to obtain 16.3 g of white needle-like product, which is 7-hydroxy- 4-methylcoumarin, the yield was 92.5%. The qualitative characterization data of the obtained 7...

Example Embodiment

[0037] Example 2 Preparation of Coumarin Derivatives

[0038] Add 7-hydroxy-4methylcoumarin (1.7g, 10.0mmol) and industrial ethanol (15.0ml) to a 25ml single-neck flask equipped with a magnetic stirrer and stir well at room temperature until dissolved, and then add 40.0% methylamine by mass fraction The aqueous solution (1.1ml, 10.0mmol) and the 37.5% formaldehyde solution (1.5ml, 20.0mmol) by mass fraction were slowly heated to 80°C, and the reaction was refluxed for 5 hours. TLC confirmed the end of the reaction. The reaction solvent was removed by rotary evaporation to obtain an oily substance, water (20.0ml) was added to solidify the oily substance, and the crude yellow coumarin derivative was obtained by suction filtration, washed with water (60ml) three times, and recrystallized by absolute ethanol to obtain 1.9g The light yellow product is the desired coumarin derivative①, with a yield of 82.1%. The structural formula of compound ① is:

[0039]

[0040] Attached figure 1 I...

Example Embodiment

[0041] Example 3-9 Preparation of Coumarin Derivatives

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

[0043] Table 1:

[0044]

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PUM

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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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