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A kind of preparation method of acacetin

The technology of acacetin and compound is applied in the field of preparation of acacetin, which can solve the problems of cumbersome operation, high cost and low yield, and achieve the effect of simple operation, low cost and high yield

Active Publication Date: 2019-05-14
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The technical problem to be solved by the present invention is to provide a kind of preparation method of acacetin in order to overcome the defects of low yield, high cost and cumbersome operation of the existing preparation method of acacetin

Method used

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  • A kind of preparation method of acacetin
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  • A kind of preparation method of acacetin

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Under the conditions of anhydrous, oxygen-free, and nitrogen protection, compound 2 (1.1g) and compound 3 (3.1g) were placed in a 50ml reaction flask, 4-dimethylaminopyridine (53mg) was added, and at a temperature of 200°C The reaction was carried out for 1.5 hours. After cooling, a solid precipitated out. Suction filtration and column chromatography gave 2.2 g of acacetin, with a yield of 89%, HPLC purity of 99.35%, and mp: 266°C.

Embodiment 2

[0026] Under the conditions of anhydrous, oxygen-free, and nitrogen protection, compound 2 (1.1g) and compound 3 (3.9g) were placed in a 50ml reaction flask, 4-pyrrolidinylpyridine (130mg) was added, and at a temperature of 180°C, The reaction was carried out for 3 hours. After cooling, a solid precipitated out. Suction filtration and column chromatography gave 2.1 g of acacetin, with a yield of 86%, HPLC purity of 97.8%, and mp: 264°C.

Embodiment 3

[0028] Under the conditions of anhydrous, oxygen-free, and nitrogen protection, compound 2 (1.1g) and compound 3 (1.9g) were placed in a 50ml reaction flask, tri-n-butylphosphine (133mg) was added, and at a temperature of 190°C, The reaction was refluxed for 2 hours. After cooling, a solid precipitated out. Suction filtration and column chromatography gave 1.86 g of acacetin with a yield of 75%. HPLC purity was 99.5%, and mp: 267°C.

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Abstract

A preparing method of acacetin is disclosed. The method includes subjecting a compound 2 and a compound 3 to a cyclization reaction under the existence of a catalyst, wherein the catalyst is one or more selected from 4-dimethylaminopyridine, 4-pyrrolidinopyridine and tri-n-butylphosphine, and the reaction is performed at 150-200 DEG C. The method is high in yield, low in cost, simple in operation and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of acacetin. Background technique [0002] Acacetin is isolated and extracted from Saussurea tianshanensis, can specifically act on human cardiomyocytes, and has anti-atrial fibrillation biological activity. Acacetin is expected to be developed into a new type of anti-atrial fibrillation medicine. Its structural formula is as follows: [0003] [0004] The content of acacetin in plants is low, the extraction and separation are difficult and the efficiency is low, and its synthesis is as follows: [0005] Chatterjee A., Phytochemistry, 1981,20(7), 1760-1761 recorded that phloroglucinol was used as a raw material, first reacted with boron trifluoride and acetic acid to obtain 2,4,6-trihydroxyacetophenone, and then reacted with The important intermediate diketone was obtained by the action of p-methoxybenzoyl chloride, and then reacted with potassium hydroxide; the intermediate diketone was reacted with s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30
Inventor 林峰江雯韩金娥陈建丽曹运华
Owner SHANGHAI INST OF PHARMA IND CO LTD
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