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Method for preparing (Z)-3'-hydroxy-3,4',5-trimethoxy diphenylethene

A technology of trimethoxystilbene and dimethoxyacetophenone, which is applied in the field of -3'-hydroxyl-3, can solve the problem of long reaction time in the step of bromine-to-hydroxyl, difficulty in realizing large-scale preparation, and cis-selectivity. low problems, to achieve the effect of low price, low cost and high cis-selectivity

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, this method still has problems such as cumbersome operation procedures, long reaction time in the step of changing bromine to hydroxyl, relatively low cis-selectivity, and low yield, making it difficult to achieve large-scale preparation

Method used

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  • Method for preparing (Z)-3'-hydroxy-3,4',5-trimethoxy diphenylethene
  • Method for preparing (Z)-3'-hydroxy-3,4',5-trimethoxy diphenylethene
  • Method for preparing (Z)-3'-hydroxy-3,4',5-trimethoxy diphenylethene

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Experimental program
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Effect test

Embodiment 1

[0040]1.52g (0.010mol) of 3,5-dihydroxyacetophenone and 10ml of water were added to the reaction flask, and 1.2g (0.030mol) of sodium hydroxide (prepared as an aqueous solution, The concentration is about 20% by mass) and 2.36ml (0.025mol) of dimethyl sulfate solution. After about 1.5h of dropwise addition, continue to stir and react for 1h. 1.73 g of solid 3,5-dimethoxyacetophenone, yield 96.11%.

Embodiment 2

[0042] Add 1.52g (0.010mol) of 3,5-dihydroxyacetophenone and 10ml of water into the reaction flask, and add 0.80g (0.020mol) of about 20% by mass of hydrogen hydroxide dropwise while stirring in an ice-water bath (0°C). Sodium aqueous solution and 1.89ml (0.020mol) of dimethyl sulfate solution, about 1h after the dropwise addition, continue to stir and react for 1.5h, pour the reaction solution into 20ml of ice water and let it stand for cooling, and suction filter to obtain a brown solid 3,5- Dimethoxyacetophenone 1.21g, yield 67.22%.

Embodiment 3

[0044] 1.52g (0.010mol) of 3,5-dihydroxyacetophenone and 10ml of water were added to the reaction flask, and 2.40g (0.060mol) of about 20% by mass aqueous sodium hydroxide solution and 4.72ml (0.050mol) of dimethyl sulfate solution, about 3h after the dropwise addition, continue to stir the reaction for 6h, pour the reaction solution into 20ml of ice water and let it cool down, then suction filter to obtain brown solid 3,5-dimethoxy Acetophenone 1.37g, yield 76.11%.

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Abstract

The invention discloses a method for preparing (Z)-3'-hydroxy-3,4',5-trimethoxy diphenylethene, comprising the following steps: taking 3,5-dihydroxyacetophenone as raw material, and then obtaining 3,5-dimethoxy hypnone by methylation reaction under the alkaline condition; then obtaining 3,5-dimethoxyphenylacetic acid by Willgerodt-Kindler rearrangement and hydrolysis reaction; enabling the 3,5-dimethoxyphenylacetic acid and isovanillin to carry out Perkin reaction to obtain (E)-2-(3',5'-dimethoxyphenyl)-3-(3'-hydroxy-4'-methoxyphenyl)crylic acid, and then obtaining the target compound, i.e. the (Z)-3'-oxhydryl-3,4',5-trimethoxy diphenylethene, by decarboxylic reaction. The raw materials of 3,5-dihydroxyacetophenone and isovanillin adopted by the invention have low price and are easy to obtain. The technical process has the advantages of simple operation, good cis-selectivity and high yield.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a preparation method of (Z)-3'-hydroxy-3,4',5-trimethoxystilbene. Background technique [0002] M.Roberti et al. (J.Med.Chem, 2003, 46, 3546) designed and synthesized (Z)-3'-hydroxyl-3,4',5-trimethyl Oxystilbene, the compound has a cis-stilbene skeleton structure. Relevant activity data show that the compound has a strong inhibitory activity of HL-60 cell proliferation (IC 50 0.03μM) and the activity of inducing apoptosis in HL-60 cells (AC 50 0.04μM), and also has a strong inhibitory activity against multidrug-resistant HL-60R cells (IC 50 0.025 μM, AC 50 is 0.03 μM). Therefore, the compound has high research and development value, and is expected to be applied in tumor and other related therapeutic fields. [0003] The synthetic route disclosed by M.Roberti et al. is: first protect the hydroxyl group, construct the skeleton of the stilbene compound through th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/18
Inventor 邹永孙洪宜肖春芬魏文林慧贞
Owner 中科检测技术服务(广州)股份有限公司
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