Preparation method of 4-hydroxy aurone compound

A compound, the technology of dihydroxyacetophenone, which is applied in the field of synthesis of hydroxyuranone compounds, can solve the problems such as the method for preparing 4-hydroxyuranone compounds is not clearly disclosed, the reaction time is long, the reaction steps are cumbersome and the like, and the product yield is achieved. The effect of high, short reaction time and low raw material price

Inactive Publication Date: 2013-03-27
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this preparation method has a series of problems such as cumbersome reaction steps and long reaction time; and this preparation method does not clearly disclose the method for preparing 4-hydroxyaurone compound

Method used

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  • Preparation method of 4-hydroxy aurone compound
  • Preparation method of 4-hydroxy aurone compound
  • Preparation method of 4-hydroxy aurone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Preparation of 2'-hydroxy-6'-methoxymethoxyacetophenone

[0041] With 4.50g (29.6mmol) 2', 6'-dihydroxyacetophenone, 8.46g (61.3mmol) anhydrous K 2 CO 3 , 73.2mL of acetone was put into a 100mL two-necked bottle, and stirred vigorously for 1h in an oil bath at 50°C. Then, slowly dropwise added 2.4mL (30 mmol) chloromethyl methyl ether into the two-necked flask, and continued the reaction for 5h after the dropwise addition. The reaction solution was filtered, and the residue was rinsed with a small amount of acetone; the filtrate and washings were collected and evaporated to dryness to remove acetone. Using a mixture of petroleum ether and ethyl acetate as the eluent, pass through a silica gel chromatography column to obtain 4.80 g of a colorless oily liquid, namely 2'-hydroxy-6'-methoxymethoxyacetophenone, with a yield of 82.7% . Among them, V (petroleum ether) / V (ethyl acetate)=10:1.

[0042] (2) Preparation of 2'-hydroxy-6'-methoxymethoxy-4''-N, N-dimethylami...

Embodiment 2

[0053] (1) Using the method of step (1) in Example 1 to prepare 2'-hydroxy-6'-methoxymethoxyacetophenone;

[0054] (2) Add 0.49g (3.3mmol) 4-(N,N-dimethylamino)benzaldehyde, 0.65g (3.3mmol) 2'-hydroxy-6'-methoxymethoxyacetophenone into 30mL Then add 20 mL of 10% sodium hydroxide ethanol solution dropwise, and stir at room temperature for 18 h. Then, the product in the flask was poured into ice water, stirred, and allowed to stand. After the layers were separated, the upper layer was poured off (removing ethanol); then 90 mL of dichloromethane was added for extraction. Purify the extract with a silica gel chromatography column, the eluent is a mixture of dichloromethane and petroleum ether; the collected components are evaporated to dryness to obtain a red solid (2'-hydroxy-6'-methoxymethoxy Base-4''-N, N-dimethylamino-chalcone) 0.48g, yield 44.1%. Wherein, V (methylene chloride) / V (petroleum ether)=1:1.

[0055] (3) Using the method of step (3) in Example 1 to prepare 4'-N,...

Embodiment 3

[0058] (1) Preparation of 2'-hydroxy-6'-methoxymethoxyacetophenone

[0059] With 4.50g (29.6mmol) 2', 6'-dihydroxyacetophenone, 8.46g (61.3mmol) anhydrous K 2 CO 3 , 73.2mL of anhydrous acetone was put into a 100mL two-necked bottle, and stirred vigorously for 1h under the condition of an oil bath at 55°C. Then, 6.0 mL (78 mmol) of chloromethyl methyl ether was slowly added dropwise into the two-necked flask, and the reaction was continued for 6 h after the dropwise addition. The reaction solution was filtered, and the residue was rinsed with a small amount of acetone; the filtrate and washings were collected and evaporated to dryness to remove acetone. Using a mixture of petroleum ether and ethyl acetate as the eluent, pass through a silica gel chromatography column to obtain 5.62 g of a colorless oily liquid, which is 2'-hydroxy-6'-methoxymethoxyacetophenone, with a yield of 96.8% . Among them, V (petroleum ether) / V (ethyl acetate)=10:1.

[0060] (2) Preparation of 2'-h...

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Abstract

The invention relates to a synthesis method of a hydroxy aurone compound, and particularly relates to a preparation method of a 4-hydroxy aurone compound. The preparation method is as below: reacting raw materials comprising 2',6'-dihydroxy acetophenone and a benzaldehyde derivative; first protecting 2',6'-dihydroxy acetophenone with one hydroxy; then conducting condensation and cyclization on the 2',6'-dihydroxy acetophenoneand benzaldehyde derivative; and conducting deprotection to obtain the 4-hydroxy aurone compound. The 4-hydroxy aurone compound has a structural formula as below; and R represents any substituent group. Compared with the existing method, the preparation method provided by the invention has advantages of low price of raw materials, high yield, short reaction time, simple and mild reaction conditions, and simple operation, etc.

Description

technical field [0001] The invention relates to a method for synthesizing a class of hydroxyarangerone compounds, in particular to a method for preparing a 4-hydroxyarangerone compound. Background technique [0002] Orange ketones have a wide range of biological activities, such as inhibiting cell proliferation, anti-tumor, alleviating and treating diabetic syndrome, anti-aging, etc.; at the same time, they also have the effect of inhibiting weeds. [0003] Patent CN101914081 discloses a method for synthesizing orange ketones. The raw materials used are substituted phenol and chloroacetonitrile, zinc chloride is used as a catalyst, diethyl ether is used as a solvent, hydrochloric acid gas is introduced, and the reaction is carried out at -10-10°C 6-72h, to obtain intermediate IV; intermediate at 60-120°C, hydrolysis, ring closure, time 1-2h, to obtain intermediate V; intermediate V and aromatic aldehyde, using ethanol aqueous solution as the medium, 10-30°C , reacted for 12...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83
Inventor 曹笃霞孙云辉陈会会马琳
Owner UNIV OF JINAN
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