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Preparation of tans-3,5- dihydroxy-4'- acetylamido-stilbene

A technology of acetamidostilbene and dihydroxyl, which is applied in the preparation of carboxylic acid amides, the preparation of organic compounds, organic chemistry, etc., can solve the problems of large dosage and high cost of chemical synthesis, and achieve fast reaction speed and high selectivity. High effect with few side effects

Inactive Publication Date: 2013-11-13
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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Problems solved by technology

However, resveratrol is quickly consumed in the organism, and its half-life is only 4 hours. The dosage is very large, and it is very limited to obtain resveratrol from plant extracts. The chemical synthesis of resveratrol is very expensive. Therefore, it is of great significance to modify and optimize the structure of resveratrol to find a new generation of resveratrol derivatives with higher efficiency and lower toxicity.

Method used

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  • Preparation of tans-3,5- dihydroxy-4'- acetylamido-stilbene

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Embodiment 1

[0016] In a 500 ml three-necked flask, add p-acetamidobenzyl chloride (18.36 g, 0.1 mol) and triethyl phosphite (33.23 g, 0.2 mol) successively, continuously stir the reaction at 130°C for 4 hours, and depressurize Distill off excess triethyl phosphite, add 3.6 grams of sodium hydride solid base and 3,5-dimethoxybenzaldehyde (15.2 grams) to the residue, add 250 milliliters of diethyl ether as a solvent for the reaction, at 80 ° C The reaction was stirred at high temperature for 4 hours. After cooling, the reaction mixture was fully washed with saturated brine, several layers were separated, dried with anhydrous sodium sulfate, and diethyl ether was distilled off to obtain the solid product trans-3,5-dimethoxy- 4'-Acetamido stilbene, the solid product trans-3,5-dimethoxy-4'-acetamido stilbene was added to a three-necked flask, and 250 ml of dry dichloromethane was added as a solvent, cooled To about 0 ℃, under the protection of nitrogen, slowly add boron tribromide (28 ml,...

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Abstract

The invention relates to preparation of a novel resveratrol derivative trans-3,5-dihydroxy-4'- acetylamido-stilbene, and belongs to the fields of organic chemistry and food chemistry. The invention aims to solve the technical problems by providing a preparation process of the resveratrol derivative tans-3,5-dihydroxy-4'- acetylamido-stilbene, wherein the preparation process has mild reaction conditions, high reaction selectivity, little side reaction, simple separation of products and high yield. The preparation process is characterized in that raw materials including 3,5-dimethoxybenzaldehyde, p-acetamido benzyl chloride, triethyl phosphite and boron tribromide are subjected to three step of chemical reactions to obtain the product trans-3,5-dihydroxy-4'- acetylamido-stilbene.

Description

technical field [0001] The invention belongs to the field of organic chemistry and food chemistry, and it relates to a novel resveratrol derivative trans 3,5-dihydroxy-4'-acetamidostilbene (English name is: trans -3,5-dihydroxy-4 ′ -acetylamido-stilbene), this new structure compound is expected to be used in health food and cardiovascular disease treatment, cancer prevention, and immunomodulatory drugs. Background technique [0002] Resveratrol (resveratrol) is a phytoalexin widely present in fruits, traditional Chinese medicine and wine, and it is also the main substance in red wine that exerts cardiovascular protection. It has a wide range of biological activities, such as anti-cancer, anti-atherosclerosis, anti-coagulation, anti-oxidation, anti-bacterial, immune regulation and neuroprotection. Because it is closely related to human health and diet, research on the pharmacological effects of resveratrol has been in-depth in recent years, and breakthroughs have been made ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/25C07C231/12
Inventor 郑兴良罗丹高鸿盛
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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