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A kind of preparation method of resveratrol compound

A technology of resveratrol and compounds, which is applied in the field of preparation of resveratrol compounds, can solve the problems of poor selectivity of resveratrol ethers, difficult configuration of carbon-carbon double bonds, and strong irritation

Active Publication Date: 2021-09-17
HANGZHOU NORMAL UNIVERSITY +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has disadvantages such as difficulty in determining the configuration of the carbon-carbon double bond, poor selectivity of resveratrol ether, and poor deprotection selectivity, which restrict its development.
Moreover, boron halides and aluminum halides are generally used as dealkylation reagents in the existing process, which is relatively harmful to the environment, and these substances are highly irritating, and will decompose or even cause explosions when exposed to water, and there are certain safety hazards

Method used

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  • A kind of preparation method of resveratrol compound
  • A kind of preparation method of resveratrol compound
  • A kind of preparation method of resveratrol compound

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preparation example Construction

[0026] The invention provides a kind of preparation method of resveratrol compound, comprises the steps:

[0027] (1) Alkoxy substituted benzyl halides, alkoxy substituted benzaldehydes and metal catalysts undergo oxidative addition and reduction elimination reactions to obtain alkoxy substituted benzophenones;

[0028] (2) Reduction, trans-elimination and selective debenzylation of the alkoxy-substituted benzophenone and a metal catalyst occur in a hydrogen atmosphere to obtain resveratrol compounds.

[0029] The reaction formula of the preparation method provided by the present invention is shown in formula (1):

[0030]

[0031] Wherein, X is Cl, Br or I, R 1 and R 3 independently methoxy or benzyloxy, R 2 and R 4 independently methoxy, benzyloxy or hydrogen, R 5 and R 7 independently methoxy or hydroxy, R 6 and R 8 are independently methoxy, hydroxy or hydrogen. In the preparation method of the present invention, hydrogenation reduction, trans elimination and s...

Embodiment 1

[0056] 67.7 grams of 3,5-dibenzyloxybenzyl chloride, 42.4 grams of 4-benzyloxybenzaldehyde, 2 grams of 5wt% palladium carbon catalyst and 400 grams of isopropanol were mixed, heated to 80 ° C for 4 hours, and the The resulting reaction solution was cooled to below 25°C; the gas in the reaction vessel was replaced with hydrogen, and then hydrogen was introduced to a pressure of 8kg f / cm 2 Then, the temperature was raised to 100°C, and the reaction was continued for 5 hours; the resulting reaction solution was filtered to recover the catalyst, the filtrate was evaporated to dryness, and the evaporated solid was heated to 80°C with 50 grams of toluene to dissolve, then cooled to 10°C, filtered and dried to obtain 40.5 gram of resveratrol, the yield is 88.8%, and the purity tested by liquid chromatography is 99.6%.

[0057] The product obtained in this embodiment is characterized by NMR, and its hydrogen spectrogram is as follows: figure 1 As shown, compare it with figure 2 Com...

Embodiment 2

[0059] 37.3 grams of 3,5-dimethoxybenzyl chloride, 42.4 grams of 4-benzyloxybenzaldehyde, 4.24 grams of 5wt% palladium carbon catalyst and 400 grams of toluene were mixed, heated to 120 ° C for 3 hours, and the resulting reaction Cool the solution to below 25°C; replace the gas in the reaction vessel with hydrogen and feed hydrogen to a pressure of 8kg f / cm 2 , then heated up to 150°C, and continued to react for 3 hours; the obtained reaction solution was filtered to recover the catalyst, the filtrate was evaporated to dryness, and the evaporated solid was heated to 85°C with 50 grams of toluene to dissolve, then cooled to 5°C, filtered and dried to obtain 44.5g Pterostilbene, the yield is 86.9%, and the purity is 99.5% by liquid chromatography.

[0060] The product obtained in this embodiment is characterized by NMR, and its hydrogen spectrogram is as follows: image 3 shown by image 3 It can be seen that the obtained pterostilbene is in the trans structure.

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Abstract

The invention provides a preparation method of resveratrol compounds, belonging to the technical field of organic synthesis. In the present invention, first, alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and metal catalyst undergo oxidative addition and reduction elimination reactions to obtain alkoxy-substituted diacetophenone; then the alkoxy-substituted diphenylethyl Reduction, trans-elimination and selective debenzylation of ketones and metal catalysts in a hydrogen atmosphere give resveratrol compounds. In the preparation method of the present invention, hydrogenation reduction, trans elimination and selective debenzylation reactions can be realized through a one-pot method, and the reaction directly obtains trans olefins, avoiding the generation of isomers; the reaction selectively catalyzes debenzylation Benzyl removes Lewis acid from the source, and has the advantage of high yield, which is a green and environmentally friendly process. Experimental results show that the products obtained by the preparation method provided by the present invention are all trans-olefins, the purity can reach more than 99.5%, and the yields are all above 80%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of resveratrol compounds. Background technique [0002] Resveratrol products are a class of non-flavonoid polyphenolic compounds containing stilbene structures, including resveratrol, pterostilbene, oxidized resveratrol, piceatanol, etc., which are naturally present in grapes, mulberries, Antioxidants in peanuts and knotweed. Since its appearance, resveratrol has been widely used in medicine, health care products and other fields due to its good anti-inflammatory, anti-cancer and anti-oxidation effects. The latest research shows that pterostilbene has a moderate inhibitory effect on cyclooxygenase COX-1, but only weak inhibitory activity on COX-2, and its anti-inflammatory and antibacterial effects are more obvious, and its antifungal activity is 5 times that of resveratrol. more than double. Resveratrol derivatives have better quality and strong...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/215C07C37/00C07C43/23C07C41/26C07C43/215C07C41/18C07C49/84C07C45/68
CPCC07B2200/09C07C37/002C07C41/18C07C41/26C07C45/68C07C49/84C07C43/23C07C43/215C07C39/215B01J23/44B01J25/02C07C37/055C07C39/21C07C37/20C07C37/60C07C37/84C07C45/45C07C39/205
Inventor 徐伟明李万梅李小玲章鹏飞汪劲松柴科杰
Owner HANGZHOU NORMAL UNIVERSITY
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