Compound (E)-4-hydroxy-3,5-dimethoxystilbene and preparation thereof

A technology of dimethoxystilbene and dimethoxybenzaldehyde, which is applied in the field of polyhydroxystilbene compound-4-hydroxy-3, can solve the problems of poor stereoselectivity, low yield, and many reaction steps, and achieve the synthesis The effect of short route, high efficiency and mild reaction conditions

Inactive Publication Date: 2008-07-23
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In a word, these methods have disadvantages such as many reaction steps, need for protection and deprotection, poor stereoselectivity, low yield, and need to use a large amount of organic solvents.

Method used

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  • Compound (E)-4-hydroxy-3,5-dimethoxystilbene and preparation thereof
  • Compound (E)-4-hydroxy-3,5-dimethoxystilbene and preparation thereof
  • Compound (E)-4-hydroxy-3,5-dimethoxystilbene and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] (1) Activation of zinc powder: wash off the oxide film on the surface of zinc powder with 2 to 5% dilute hydrochloric acid, wash the zinc powder with water, acetone, ether, and ethanol in sequence, remove inorganic salts and moisture in the zinc powder, vacuum dry, Cool to obtain activated zinc powder;

[0040] (2) Preparation of (E)-4-hydroxyl-3,5-dimethoxystilbene: 4-hydroxyl-3,5-dimethoxybenzaldehyde and activated zinc powder are added in a molar ratio of 1:1.15 In a dry reactor, under the protection of nitrogen, gradually add 4-hydroxy-3,5-dimethoxybenzaldehyde 2 times the molar amount of trimethyl chloride to the reactor at a rate of 3-5ml / min. Silane and 1.1 times the molar amount of benzyl bromide were reacted under stirring for 2 hours. After the reaction was completed by TLC, 1 times the molar amount of 4-hydroxy-3,5-dimethoxybenzaldehyde was added successively. Ethyl ether and 2 times The molar amount of saturated ammonium chloride solution was stirred, and t...

Embodiment 2

[0042] (1) Activation of zinc powder: same as embodiment one.

[0043] (2) Preparation of (E)-4-hydroxyl-3,5-dimethoxystilbene:

[0044] Add 4-hydroxyl-3,5-dimethoxybenzaldehyde and activated zinc powder into the dry reactor at a molar ratio of 1:1.2, and feed into the reactor at 3-5ml / min under the protection of nitrogen. Gradually add 2.25 times the molar amount of 4-hydroxy-3,5-dimethoxybenzaldehyde trimethylchlorosilane and 1.2 times the molar amount of benzyl bromide, react under stirring for 4 hours, TLC tracking until the reaction is complete Finally, add 4-hydroxy-3,5-dimethoxybenzaldehyde 1.5 times the molar amount of ether and 2.5 times the molar amount of saturated ammonium chloride solution, stir, separate the organic phase, extract the aqueous phase with ether, and combine into the organic phase, and dried with anhydrous magnesium sulfate, and separated by column chromatography (silica gel, 300-400; petroleum ether: ethyl acetate, 10:1) after evaporating the solv...

Embodiment 3

[0046] (1) Activation of zinc powder: same as embodiment one.

[0047] (2) Preparation of (E)-4-hydroxyl-3,5-dimethoxystilbene:

[0048] Add 4-hydroxyl-3,5-dimethoxybenzaldehyde and activated zinc powder into the dry reactor at a molar ratio of 1:1.3, and feed into the reactor at 3-5ml / min under the protection of nitrogen. 4-Hydroxy-3, 5-dimethoxybenzaldehyde 1.8 times the molar amount of trimethylchlorosilane and 1.3 times the molar amount of benzyl bromide were gradually added, and reacted for 3 hours under stirring, and TLC tracked until the reaction was complete Finally, 4-hydroxy-3,5-dimethoxybenzaldehyde 1.0 times the molar amount of ether and 2.5 times the molar amount of saturated ammonium chloride solution were added successively, stirred, the organic phase was separated, the aqueous phase was extracted with ether, and combined into the organic phase, and dried with anhydrous magnesium sulfate, and separated by column chromatography (silica gel, 300-400; petroleum et...

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Abstract

The invention discloses a new method of synthesizing polyhydrostilbene compound (E)-4-hydroxy-3, 5-dimethoxy stilbene, which is characterized in that: Lewis acid is used as catalyst; metallic zinc powder is used for promoting the reaction for the 4-hydroxy-3, 5-dimethoxy benzaldehyde and benzyl bromide for one pot reaction at ambient temperature, thereby realizing one-step synthesis upon 4-hydroxy-3, 5-dimethoxy stilbene with short synthesis line, high efficiency and high reaction yield (reaching more than 70%). The new method of synthesizing polyhydrostilbene compound (E)-4-hydroxy-3, 5-dimethoxy stilbene has the advantages that: the carbonyl of the 4-hydroxy-3, 5-dimethoxy benzaldehyde is directly converted to relative carbon-carbon double bond and all are trans configuration, thereby showing good stereo selectivity; functional group at the substrate can be reserved and can be completely guided into addition products without needing protection and de-protection of the functional group, thereby showing good chemical selectivity; the synthesizing method does not need any solvent but use cheap and nontoxic metallic zinc powder, thereby avoiding pollution of organic solvent on environment and being friendly upon environment.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to a preparation method of polyhydroxystilbene compounds, in particular to a preparation method of polyhydroxystilbene compounds (E)-4-hydroxy-3,5-dimethoxystilbene. Background technique [0002] Stilbenes is a general term for a class of substances with a stilbene core structure or its polymers. Polyhydroxystilbenes (Polyhydroxystilbenes) is a class of stilbenes with phenolic hydroxyl substituents. Natural polyhydroxystilbenes are widely found in Chinese herbal medicines such as knotweed, veratrum, rhubarb, and fruit foods such as grapes and mulberries, which can enhance plant resistance to pests and diseases , so called phytoalexins. In recent years, there have been many reports on the biological activity of polyhydroxystilbene. In addition to the clear antibacterial effect, it has also been found to have various biological activities such as anti-oxidation, anti-thrombotic, blood-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/30
Inventor 王进贤严文君
Owner NORTHWEST NORMAL UNIVERSITY
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