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Methods for preparing E-3,5-dimethoxy-4'-oxhydryl diphenylethene and derivative thereof

A technology of hydroxystilbene and dimethoxyacetophenone, applied in the field of E-3, can solve the problems of low yield, cumbersome steps, difficult separation, etc., and achieves high selectivity, simple post-processing, and atom economy. Good results

Inactive Publication Date: 2010-03-10
中科检测技术服务(广州)股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when these methods synthesize the target compound, either protection and deprotection of the hydroxyl group are required; or group conversion is required, and a mixture of cis-trans isomers is easily obtained, which is difficult to separate and requires further conversion, and the steps are cumbersome and the yield is low. lower

Method used

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  • Methods for preparing E-3,5-dimethoxy-4'-oxhydryl diphenylethene and derivative thereof
  • Methods for preparing E-3,5-dimethoxy-4'-oxhydryl diphenylethene and derivative thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (1) Get 1.52g (10mmol) of 3,5-dihydroxyacetophenone, start dropwise addition of mass concentration simultaneously under stirring at room temperature and be 10%NaOH (20mmol) solution and Me 2 SO 4 2ml (20mmol), continue to stir for 2h after the dropwise addition, after the reaction is completed, pour the reaction solution into ice water and stir, a large amount of solids are precipitated, after standing, filter with suction, and the filter cake is air-dried to obtain 3,5-dimethoxybenzene Ethyl ketone 1.62g, yield 90%.

[0033] (2) Take 1.80g (10mmol) of 3,5-dimethoxyacetophenone, 0.64g (20mmol) of sulfur, 3ml (30mmol) of morpholine, and 0.05g (0.3mmol) of p-toluenesulfonic acid, at 120°C Stir for 8 hours, stop heating after the disappearance of the raw materials, add a mass concentration of 20% NaOH (50mmol) solution and 0.13g (0.04mmol) of tetrabutylammonium bromide to the reaction flask after the reaction liquid is cooled, and react at 100°C for 8 hours , then pour t...

Embodiment 2

[0039] (1) Get 1.52g (10mmol) of 3,5-dihydroxyacetophenone, start dropwise addition of mass concentration simultaneously under stirring at room temperature and be 18%NaOH (22mmol) solution and Me 2 SO 4 2.2ml (22mmol), continue to stir for 2h after the dropwise addition, after the reaction is completed, pour the reaction solution into ice water and stir, a large amount of solids are precipitated, after standing, filter with suction, and the filter cake is air-dried to obtain 3,5-dimethoxy Acetophenone 1.64g, yield 91%.

[0040] (2) Take 1.80g (10mmol) of 3,5-dimethoxyacetophenone, 0.64g (20mmol) of sulfur, 3ml (30mmol) of morpholine, and 0.06g (0.35mmol) of p-toluenesulfonic acid, at 120°C Stir for 8 hours, stop heating after the disappearance of the raw materials, add a mass concentration of 22% NaOH (50mmol) solution and 0.16g (0.05mmol) of tetrabutylammonium bromide to the reaction flask after the reaction liquid is cooled, and react at 100°C for 6 hours , then pour the r...

Embodiment 3

[0045] (1) Get 1.52g (10mmol) of 3,5-dihydroxyacetophenone, and the mass concentration is 20% NaOH (22mmol) aqueous solution, start to drop NaOH solution and Me 2 SO 4 2.2ml (22mmol), continue to stir for 3h after the dropwise addition, after the reaction is completed, pour the reaction solution into ice water and stir, a large amount of solids are precipitated, after standing, filter with suction, and the filter cake is air-dried to obtain 3,5-dimethoxy Acetophenone 1.66g, yield 92%.

[0046] (2) Take 1.80g (10mmol) of 3,5-dimethoxyacetophenone, 0.48g (15mmol) of sulfur, 3ml (30mmol) of morpholine, and 0.05g (0.3mmol) of p-toluenesulfonic acid, at 115°C Stir for 9 hours, stop heating after the disappearance of the raw materials, add a mass concentration of 28% NaOH (50 mmol) aqueous solution and 0.16 g (0.05 mmol) of tetrabutylammonium bromide to the reaction flask after the reaction liquid is cooled, and react at 100 ° C for 7 hours Pour the reaction solution into a beaker...

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Abstract

The invention discloses two methods for preparing E-3,5-dimethoxy-4'-oxhydryl diphenylethene and a derivative thereof, comprising the following steps: firstly, methylating 3,5-ihydroxyacetophenone toobtain 3,5-dimethoxy hypnone; then preparing 3,5-methoxyphenylacetic acid by Willgerodt-Kindler rearrangement and hydrolysis reaction; enabling the 3,5-methoxyphenylacetic acid and a 4-hydroxybenzeneformaldehyde compound to carry out Perkin reaction to obtain E-2,3-diaryl crylic acid; finally obtaining the E-3,5-dimethoxy-4'-oxhydryl diphenylethene and the derivative thereof by decarboxylation and isomerization reaction and hydrolysis (or hydrolysis, decarboxylation and isomerization) reaction. An all-trans product obtained by using the method has the advantages of good atomic economy, high yield, convenient operation, low cost, easy realization of mass preparation, and the like.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of E-3,5-dimethoxy-4'-hydroxystilbene and derivatives thereof. Background technique [0002] E-3,5-dimethoxy-4'-hydroxystilbene and its derivatives (structural formula shown in formula 1) are a class of compounds with important biological activity. Among them, the most representative red sandalwood stilbene (Pterostilbene) exists in various natural plants such as blue strawberry, Indian jina tree and Chinese Guangxi dracaena, and has anti-oxidation, blood lipid lowering, and inhibition of COX-1 and COX -2. Anticancer and antifungal effects (Current Clinical Pharmacology, 2006, (1) 1: 81-101), and it is also the main active ingredient of Ayurvedic, a drug for treating diabetes in Indian herbal medicine. The latest research has found that pterostilbene has the activity of activating peroxisome proliferator-activated receptor α (PPARα), and PPARα is closely rel...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/26C07C41/18
Inventor 邹永肖春芬孙洪宜
Owner 中科检测技术服务(广州)股份有限公司
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