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Method for synthesizing stilbenoids by hydrochloric acid heterogeneous chlorination

A stilbene compound and heterogeneous technology, which is applied in the field of chlorination of hydrochloric acid for synthesizing stilbene compounds in heterogeneous phase, can solve the problems of separation difficulty, environmental damage, pollution and the like

Inactive Publication Date: 2010-01-27
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

Because the activity of the halogenated reagents involved in this type of synthetic method is too high, it will inevitably cause higher impurity content in the product and difficult separation; in addition, the halogenated reagents used in industrial production have serious pollution problems, such as sulfur dioxide and Phosphorus wastewater discharge, etc., will cause serious damage to the environment

Method used

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  • Method for synthesizing stilbenoids by hydrochloric acid heterogeneous chlorination
  • Method for synthesizing stilbenoids by hydrochloric acid heterogeneous chlorination
  • Method for synthesizing stilbenoids by hydrochloric acid heterogeneous chlorination

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 21-25

[0096] (2) When R 1 , R 3 , R' 1 , R' 2 , R' 4 is hydrogen; R 2 , R 4 is methoxy; R' 3 When it is an acetoxy group or an alkyl siloxy group, the final product is the structure of pterostylbene; the method is a method for synthesizing pterostilbene by hydrochloric acid heterogeneous chlorination, as in Examples 21-25;

[0097] (3) When R 1 , R 3 , R' 1 , R' 2 is hydrogen; R2 , R 4 , R' 3 , R' 4 When it is a methoxyl group, the final product is picetanol; the method is the first method for synthesizing picatanol by hydrochloric acid heterogeneous chlorination, as in Examples 31-35;

[0098] (4) When R 1 , R 2 , R' 1 , R' 3 is hydrogen; R 3 , R 4 , R' 2 , R' 4 When it is a methoxyl group, the final product is picetanol; the method is the second method for synthesizing picetanol with hydrochloric acid heterogeneous chlorination, as in Examples 41-45;

[0099] (5) When R 1 , R 3 , R' 2 , R' 4 is hydrogen; R 2 , R 4 , R' 1 , R' 3 When it is a methoxyl g...

Embodiment 41-45

[0143] Example 41-45 The second method of heterogeneous chlorination of hydrochloric acid to synthesize piceatanol

[0144]

[0145]

[0146] The method two of above-mentioned heterogeneous chlorination of hydrochloric acid to synthesize picatanol, the reaction scheme is as formula (V):

[0147]

[0148] Formula (V)

[0149] The method two of the above-mentioned heterogeneous chlorination of hydrochloric acid to synthesize piceatanol is carried out according to the following steps:

[0150] (41) Preparation A4: 3,4-dimethoxybenzyl chloride

[0151] Take 3,4-dimethoxybenzyl alcohol, add solvent, and slowly drop hydrochloric acid; after the reaction is completed, let stand to separate layers, wash the organic phase, dry, and evaporate the organic solvent to obtain product A4;

[0152] (42) Preparation B4: Diethyl 3,4-dimethoxybenzylphosphonate

[0153] A4 is mixed with triethyl phosphite, heated, refluxed, monitored by TLC, and processed af...

Embodiment 51-55

[0158] Example 51-55 Method 1 for the heterogeneous chlorination of hydrochloric acid to synthesize oxidized resveratrol

[0159]

[0160]

[0161] The method one of the above-mentioned heterogeneous chlorination of hydrochloric acid to synthesize oxidized resveratrol, its reaction route is as formula (VI):

[0162]

[0163] Formula (VI)

[0164] The first method for the heterogeneous chlorination of hydrochloric acid to synthesize oxidized resveratrol is carried out according to the following steps:

[0165] (51) Preparation A5: 3,5-dimethoxybenzyl chloride

[0166] Take 3,5-dimethoxybenzyl alcohol, add a solvent, and slowly drop hydrochloric acid; after the reaction is completed, let stand to separate layers, wash the organic phase, dry, and evaporate the organic solvent to obtain the product A5;

[0167] (52) Preparation B5: Diethyl 3,5-dimethoxybenzylphosphonate

[0168] A5 and triethyl phosphite were mixed, heated, refluxed, monitore...

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Abstract

The invention discloses a method for synthesizing stilbenoids of styrenemod, pterostilbene, piceatannol and resveratrol oxide by hydrochloric acid heterogeneous chlorination. The method takes substituted benzyl alcohol as a raw material, adopts hydrochloric acid for preparing chlorinated hydrocarbons under heterogeneous conditions and prepares the stilbenes compounds by Wittig-Horner condensation. The method is simple and easy to operate, the reactants involved in the synthesis process are safe, the products can not cause environmental pollution, the cost is low, and the yield is high, thereby being applicable to industrial production of styrenemod, pterostilbene, piceatannol and resveratrol oxide.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for synthesizing stilbene compounds through heterogeneous chlorination of hydrochloric acid. Background technique [0002] (E)-3,5-dihydroxy-4-isopropyl stilbene, (E)-3,5-dimethoxy-4'-hydroxy stilbene, (E)-3,4,3 ',5'-Tetrahydroxystyrene, (E)-2,4,3',5'-Tetrahydroxystilbene are compounds with a 1,2-stilbene skeleton, and the trade names are Benzene Moder , pterostylbene, picatanol, and oxidized resveratrol belong to stilbene compounds, and their structural formulas are as follows: [0003] [0004] Studies have shown that these compounds have high chemical and pharmaceutical activities, and their physiological activities are mainly anti-cancer, anti-bacteria and fungi, anti-blood lipids, anti-platelet aggregation, inhibition of cardiovascular disease, anti-diabetes, prevention and treatment of tissue cancer and tumors happen etc. [0005] In the literature reports, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/20C07C43/253C07C41/30
Inventor 张越赵淑春张艳艳
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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