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Oxyresveratrol synthesis method

A technology for oxidizing asparagine and a synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of long synthesis route and only 30% total yield, and achieves high yield and raw material. Easy-to-obtain, maneuverable effects

Active Publication Date: 2015-05-13
HERBALIFE LEISHUO HUNAN NATURAL PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the method of simple and efficient synthesis of oxystilbene triphenol
In 2010, Zou Yong et al. used 3,5-dihydroxyacetophenone as a raw material to construct a stilbene skeleton through methylation, Willgerodt-Kindler rearrangement and Perkin reaction, and then decarboxylated and demethylated isomerization to obtain the target product, but the synthetic route is relatively long, and the total yield is only 30% (Zhang Hongyi, Zou Yong, etc., Synthesis of oxidized resveratrol, Organic Chemistry, 2010, 30, 1574)

Method used

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  • Oxyresveratrol synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0022] The reaction equation is:

[0023]

[0024] The present invention is a kind of synthetic method of oxystilbenzyl bromide, comprising 3,5-dimethoxybenzyl bromide (compound 2 ), 2,3',4,5'-tetramethoxystilbene (compound 5 ) synthesis, oxystilbene triphenol (compound 6 )Synthesis.

[0025] 3,5-dimethoxybenzyl bromide (compound 2 )Synthesis

[0026] Add 40% HBr (24 mL, 0.12 mol) to a solution of 3,5-dimethoxybenzyl alcohol (16.8 g, 0.1 mol) in toluene (50 mL), and react at 80°C for about 4 h. After the completion of the reaction was confirmed by TLC, the toluene was spun off, and the remaining turbid solution was extracted three times with ethyl acetate (60 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was spun off to obtain a reddish-brown oily liquid. White crystals of 21.3 were obtained after recrystallization with ethyl acetate and petroleum ether, yield = 93.0%. 1 H NMR (CDCl 3 ): 6.54 (s, 2H), 6.39 (s, 1H), 4.42 (...

Embodiment 2

[0032] 3,5-dimethoxybenzyl bromide (compound 2 ), (Z)-2,3',4,5'-tetramethoxystilbene (compound 5 ) Synthesis, as described in Example 1.

[0033] Oxystilbene triphenols (compound 6 )Synthesis

[0034] In a 250 mL round-bottomed flask, add magnetite, magnesium chips (5.5 g, 0.23 mol) and anhydrous ether (30 mL), and continuously add a solution of methyl iodide (123.5 g, 0.87 mol) in ether (20 mL) under stirring. ) until the magnesium chips are completely dissolved. Then add to the reaction bottle 5 (3, 5, 2’, 4’)-tetramethoxystilbene (3 g, 0.01 mol), stirred at room temperature until completely dissolved, and the solvent was removed by spin to obtain a dark gray viscous liquid. Then react at 160 °C for 5 min, cool slowly, crush the obtained reaction system, add anhydrous ethyl acetate (50 mL) to it, and then add ice water (50 mL), and wash the water layer with ethyl acetate ( 20 mL) was extracted three times, the organic phases were combined, dried over sodium sulfate, an...

Embodiment 3

[0036] 3,5-dimethoxybenzyl bromide (compound 2 ), (Z)-2,3',4,5'-tetramethoxystilbene (compound 5 ) Synthesis, as described in Example 1.

[0037] Oxystilbene triphenols (compound 6 )Synthesis

[0038] In a 250 mL round-bottomed flask, add magnetite, magnesium chips (1.92 g, 0.08 mol) and anhydrous ether (20 mL), and continuously add a solution of methyl iodide (12.8 g, 0.09 mol) in ether (20 mL) under stirring. ) until the magnesium chips are completely dissolved. Then add the compound to the reaction vial 5 (3, 5, 2’, 4’)-tetramethoxystilbene (3 g, 0.01 mol), stirred at room temperature until completely dissolved, and the solvent was removed by spin to obtain a dark gray viscous liquid. Then react at 160 °C for 5 min, cool slowly, crush the obtained reaction system, add anhydrous ethyl acetate (50 mL) to it, and then add ice water (50 mL), and wash the water layer with ethyl acetate ( 20 mL) was extracted three times, the organic phases were combined, dried over sodium ...

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Abstract

The invention relates to an oxyresveratrol synthesis method. The method concretely comprises the following steps: reacting 3,5-dimethoxybenzyl alcohol with an aqueous solution of hydrogen bromide to obtain 3,5-dimethoxybenzyl bromide, carrying out a reflux reaction of 3,5-dimethoxybenzyl bromide and triethyl phosphite in toluene, carrying out a Witting-Horner reaction of the obtained substance and 2,4-dimethoxybenzaldehyde under the action of an alkali to obtain 2,3',4,5'-tetramethoxystilbene, and demethylating 2,3',4,5'-tetramethoxystilbene by a Grignard reagent within a very short period of time to obtain oxyresveratrol. The oxyresveratrol synthesis method has the advantages of easily available raw materials, strong maneuverability of reaction conditions, and high yield.

Description

technical field [0001] The invention belongs to the field of new preparation methods of compounds, and provides a synthesis method of oxystilbene triphenol and the preparation of intermediates thereof. Background technique [0002] Oxystilbene triphenols (also known as oxidized resveratrol, Oxyresveratrol, E-2,3',4,5'-tetrahydroxystilbene, 2,4,3',5'-tetrahydroxystilbene, CAS: 29700-22 -9), which is the 2'-hydroxylation derivative of the polyhydroxy trans-stilbene natural product resveratrol (Resveratrol, E-3', 5', 4-tetrahydroxystilbene) that has attracted much attention in recent years. Studies have shown that, as a homologue of resveratrol, oxystilbene triphenol also has good biological activities, such as anti-oxidation, anti-inflammatory, anti-thrombosis, anti-cancer, anti-cancer, anti-hyperlipidemia, antibacterial, etc. With the continuous deepening of research and development, oxystilbene triphenol is expected to be widely used in the fields of health care products, m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/21C07C37/055
Inventor 郑群怡李志伟谢朝阳鲍志超王建南
Owner HERBALIFE LEISHUO HUNAN NATURAL PROD
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