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4'-hydroxy-4,6'-dimethoxy dihydrocharcone and method for synthesizing the same

A technology of dimethoxydihydrochalcone and methoxyacetophenone is applied in the field of organic chemical synthesis technology of dihydrochalcone to achieve the effects of good platelet aggregation, inhibition of platelet aggregation, and safe and simple operation.

Inactive Publication Date: 2008-05-21
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] There is no report on the synthesis method of the new compound 4'-hydroxy-4,6'-dimethoxydihydrochalcone at home and abroad

Method used

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  • 4'-hydroxy-4,6'-dimethoxy dihydrocharcone and method for synthesizing the same
  • 4'-hydroxy-4,6'-dimethoxy dihydrocharcone and method for synthesizing the same
  • 4'-hydroxy-4,6'-dimethoxy dihydrocharcone and method for synthesizing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 2g of 2-hydroxy-4-benzyl-acetophenone (0.008mol) into a 250ml three-necked flask, and dissolve the toluene. Add 0.2 g of phase transfer catalyst benzyltriethylammonium chloride, 2 mL of dimethyl sulfate. While stirring mechanically at room temperature, 40% NaOH was slowly added dropwise to control the pH of the reaction system to be 8-9. The reaction was followed by TLC and the starting material spot disappeared in 3 hours. The organic phase was evaporated to dryness in toluene. 0.72 g of solid was obtained, which was 4-benzyloxy-2-methoxyacetophenone. Recrystallization from ethyl acetate gave 0.6 g of tan crystals. The melting point is 64.8-65.6°C. The purity detected by high performance liquid chromatography was 98.5%, and the yield was 29.3%.

[0040] in N 2 In the protected there-necked flask, add 2.8g (0.011mol) 4-benzyloxy-2-methoxyacetophenone, 1.5g (0.011mol) 4-methoxybenzaldehyde, add 100mL ethanol and 11.2g (0.2mol) KOH solution. After completion, ...

Embodiment 2

[0043] Add 2g of 2-hydroxy-4-benzyl-acetophenone (0.008mol) into a 250ml three-necked flask, and dissolve the toluene. Add 0.3 g of phase transfer catalyst benzyltriethylammonium chloride, 2.5 mL of dimethyl sulfate. Stir mechanically at room temperature while slowly adding 30% NaOH dropwise to control the pH of the reaction system to 8-9. The reaction was followed by TLC and the starting material spot disappeared in 3.5 hours. The organic phase was evaporated to dryness in toluene. 0.79 g of solid was obtained, namely 4-benzyloxy-2-methoxyacetophenone, which was recrystallized from ethyl acetate to obtain 0.7 g of brown-yellow crystals. The melting point is 64.4-65.2°C. The purity detected by high performance liquid chromatography was 98.5%, and the yield was 34.2%.

[0044] in N 2 In the protected three-necked flask, add 2.8g (0.011mol) 4-benzyloxy-2-methoxyacetophenone, 2g (0.015mol) 4-methoxybenzaldehyde, add under stirring by 150mL ethanol and 8.4 g (0.15mol) KOH so...

Embodiment 3

[0047] Add 2g of 2-hydroxy-4-benzyl-acetophenone (0.008mol) into a 250ml three-necked flask, and dissolve the toluene. Add 0.1 g of phase transfer catalyst benzyltriethylammonium chloride, 3 ml of dimethyl sulfate. While mechanically stirring at room temperature, 20% NaOH was slowly added dropwise to control the pH of the reaction system to 8-10. The reaction was followed by TLC, and the starting material spot disappeared after 5 hours. The organic phase was evaporated to dryness in toluene. 0.8 g of solid was obtained, which was 4-benzyloxy-2-methoxyacetophenone. Recrystallization from ethyl acetate gave 0.75 g of tan crystals. The melting point is 64.2-64.9°C. The purity detected by high performance liquid chromatography was 99.5%, and the yield was 36.63%.

[0048] in N 2 In the protected there-necked flask, add 2.8g (0.011mol) 4-benzyloxy-2-methoxyacetophenone, 1.89g (0.014mol) 4-methoxybenzaldehyde, add 200mL ethanol and 11.2g (0.2mol) KOH solution. After completi...

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Abstract

The present invention discloses a 4'-hydroxy-4, 6'-dimethoxy dihydrochalcone and a synthesis method thereof. The present invention considers 4-benzyloxy-2-hydroxy hypnone as the raw material to be processed for the methylation reaction when the two phases of lye and organic solvent exist, and 4-benzyloxy-2-methoxy hypnoone is obtained. Then the 4-benzyloxy-2-methoxy hypnoone and 4-methoxy benzaldehyde are processed for the aldol condensation reaction in alkaline alcohol solution to obtain a intermediate product of 4'-benzyloxy-4, 6'-dimethoxy chalcone, then the intermediate is hydrogenated tobe deoxidized when catalyst Pd / C exists, and protective group is removed from the intermediate, and finally a target product of the present invention of the 4'-hydroxy-4, 6'-dimethoxy dihydrochalconeis obtained. The operation of the method of the present invention is safe, simple and convenient; the obtained product has the high purity, the good safety of animal acute toxicity test and the good activity of resisting the platelet aggregation.

Description

technical field [0001] The invention relates to a 4'-hydroxy-4,6'-dimethoxydihydrochalcone and a synthesis method thereof, belonging to the technical field of organic chemical synthesis of dihydrochalcone. Background technique [0002] 4'-Hydroxy-4,6'-dimethoxydihydrochalcone is a type of dihydrochalcone. After searching by Scifinder, it was confirmed that it was a new compound. Dihydrochalcones are a very important class of active ingredients with antioxidant, antitumor, antidiabetic, antibacterial, and estrogen-like effects. Through in vitro activity experiments, it has been proved that it has the functions of promoting blood circulation, removing stasis and inhibiting platelet aggregation. The product has wide application and good market prospect. [0003] Its structural formula is as follows: [0004] [0005] After searching, the relevant literature of the compound with the above-mentioned synthesis similar to the parent structure is as follows: [0006] Richard...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/61A61K31/12A61P7/02
CPCY02P20/55
Inventor 雍克岚吕敬慈顾慧娟陈旭
Owner SHANGHAI UNIV
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