Coumarin derivative and preparation and application thereof

A technology of coumarin derivatives and methyl coumarin, which is applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problem of poor control of polymer materials' hydrophilicity and hydrophobicity, and difficult control of drug coating and release To achieve the effect of good drug coating and release rate, high yield and wide application prospect

Inactive Publication Date: 2018-09-28
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are reports about the benzyl chloride substitution reaction of 7-hydroxy-4-methylcoumarin directly with 4-vinylbenzyl chloride, but the disadvantage of this monomer is that the synthetic polymer material has poor control of hydrophilicity and hydrophobicity. , it is not easy to control the drug coating and release rate when used as a drug carrier

Method used

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  • Coumarin derivative and preparation and application thereof
  • Coumarin derivative and preparation and application thereof
  • Coumarin derivative and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Add 7-hydroxy-4-methylcoumarin (5g, 28.38mmol), N,N-dimethylformamide (50mL) and anhydrous potassium carbonate (3g) into the reaction tube, ultrasonically disperse for 10 minutes and use Seal the tube with a rubber stopper. The reaction tube was vigorously stirred at 85°C. After the system was stabilized and mixed uniformly, 2-bromoethanol (2.84ml, 40mmol) was injected dropwise into the reaction tube with a disposable syringe, and the reaction was vigorously stirred for 20 hours. After the reaction was completed, filter, and then drop the filtrate into ice deionized water, a white solid precipitated, washed with ice deionized water several times, and vacuumed to constant weight to obtain the intermediate 7-(2-hydroxyethoxy)-4-methanol base coumarin.

[0050] Add 7-(2-hydroxyethoxy)-4-methylcoumarin (1.1g, 5mmol), N,N-dimethylformamide (20ml), bis(2,6-bis tert-butyl-4-methylphenyl) pentaerythritol diphosphate (0.11g) and anhydrous potassium carbonate (0.83g), after ult...

Embodiment 2

[0052] According to the first step of the substitution reaction in Example 1, the intermediate 7-(2-hydroxyethoxy)-4-methylcoumarin was obtained.

[0053] Add 7-(2-hydroxyethoxy)-4-methylcoumarin (1.1g, 5mmol), N,N-dimethylformamide (20ml), bis(2,6-bis tert-butyl-4-methylphenyl) pentaerythritol diphosphate (0.11g) and anhydrous potassium carbonate (0.83g), after ultrasonic dispersion for 10 minutes, the tube was sealed with a rubber stopper, after which the reaction tube was vigorously stirred at 65°C , Introduce high-purity nitrogen for 20 minutes to remove oxygen in the reaction system and prevent 4-vinylbenzyl chloride from exploding after being mixed with air due to its active chemical properties. After the system was stabilized and mixed uniformly, 4-vinylbenzyl chloride (1.137ml, 8mmol) was injected dropwise into the reaction tube with a disposable syringe, and stirred vigorously at 65°C for 24 hours. After the reaction is finished, filter, then drop the filtrate into i...

Embodiment 3

[0055] According to the first step of the substitution reaction in Example 1, the intermediate 7-(2-hydroxyethoxy)-4-methylcoumarin was obtained.

[0056] Add 7-(2-hydroxyethoxy)-4-methylcoumarin (1.1g, 5mmol), N,N-dimethylformamide (20ml), bis(2,6-bis tert-butyl-4-methylphenyl) pentaerythritol diphosphate (0.11g) and anhydrous potassium carbonate (0.83g), after ultrasonic dispersion for 10 minutes, the tube was sealed with a rubber stopper, after which the reaction tube was vigorously stirred at 65°C , Introduce high-purity nitrogen for 20 minutes to remove oxygen in the reaction system and prevent 4-vinylbenzyl chloride from exploding after being mixed with air due to its active chemical properties. After the system was stabilized and mixed uniformly, 4-vinylbenzyl chloride (1.42ml, 10mmol) was injected dropwise into the reaction tube with a disposable syringe, and stirred vigorously at 65°C for 24 hours. After the reaction is finished, filter, then drop the filtrate into i...

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Abstract

The invention discloses a coumarin derivative and preparation and application thereof. 7-hydroxy-4-methyl coumarin as a raw material is subjected to substitution reactions with halogenated ethyl alcohol and 4-vinylbenzyl chloride in sequence, and then 7-[2-(4-vinyl benzyloxy)-ethyoxyl]-4-methyl coumarin is obtained. The method has the advantages that the operation is simple, the conditions are mild, the product is easy to purify, and the yield is high, the coumarin derivative synthesized by using the method has polymerizable double-bond elements, alkoxy flexible spacers and coumarin photosensitive groups, and when the coumarin derivative as a photosensitive monomer used for synthesis of a photostimulation response polymer material, the polymerization efficiency can be obviously improved. The water solubility and the degradability of the polymer material synthesized by using the counmarin derivative can be improved, the hydrophily and the hydrophobicity of the polymer material are moreeasily regulated and controlled, and therefore, in the use process of the polymer material as a drug carrier, the drug encapsulation and release rates can be better controlled.

Description

technical field [0001] The present invention relates to a kind of coumarin derivative namely 7-[2-(4-vinylbenzyloxy)-ethoxy]-4-methylcoumarin, also relates to 7-[2-(4-ethylene The preparation method of -ylbenzyloxy)-ethoxy]-4-methylcoumarin and 7-[2-(4-vinylbenzyloxy)-ethoxyl]-4-methylcoumarin in The application in the synthesis of photo-stimuli-responsive functional polymer materials belongs to the field of organic synthesis of fine chemical intermediates. Background technique [0002] Coumarin (also known as 1,2-benzopyrone) and its derivatives are compounds with a lactone ring structure, which not only have antibacterial, anticoagulant, anti-inflammatory and antihypertensive effects, but also some derivatives Also has anti-HIV activity and anti-tumor effect. In addition, the coumarin parent structure benzopyran itself has no fluorescence, but the substituted coumarin derivatives often have good fluorescence properties, with high fluorescence quantum yield, large Stokes ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06C08F212/32C08F220/20C08F220/34
CPCC07D311/16C08F212/32C09K11/06C09K2211/1007C09K2211/1088C08F220/20C08F220/34
Inventor 刘辉李思思
Owner CENT SOUTH UNIV
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