Method for preparing piceatannol

A technology of piceatannol and potassium tert-butoxide, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve problems such as low yield of piceatannol, and achieves safety and high purity of reactants. , easy-to-control effects

Inactive Publication Date: 2012-02-15
KPC PHARM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of this, the object of the present invention is to provide a method for preparing picetanol with a high reaction yield for the low yield of picetanol prepared by the existing method

Method used

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  • Method for preparing piceatannol
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  • Method for preparing piceatannol

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Experimental program
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Effect test

Embodiment 1

[0030] Embodiment 1: 3,4,3',5'-Tetramethoxystilbene yield comparative test in different catalysts and solvents

[0031]Dissolve 3,5-dimethoxybenzyl diethyl phosphate in different solvents, under the protection of nitrogen, drop different catalysts, keep different temperatures, stir for 1 hour, and then add 3,5-dimethoxybenzene After formaldehyde was dissolved in different solvents, it was added dropwise to the reaction system, and after the dropwise addition was completed, it was stirred at room temperature for 1 hour. After the reaction was completed, add ethyl acetate for extraction, wash with water, collect the ethyl acetate portion, and recover the solvent under reduced pressure to obtain a crude product, dissolve it with ethyl acetate and petroleum ether, filter, collect the filter cake, and dry. The solvent was recovered from the filtrate to dryness under reduced pressure, and the residue was subjected to silica gel column chromatography to finally obtain a white solid, ...

Embodiment 2

[0035] Embodiment 2: 3,4,3', the preparation of 5'-tetramethoxystilbene

[0036] Under nitrogen protection, 245 g (0.85 mol) of 3,5-dimethoxybenzyl diethyl phosphate was added to 2.5 L dimethylformamide solution, and 95.4 g (0.85 mol) of potassium tert-butyl alkoxide was added in portions. mol), control the temperature at 0°C, stir for 1 hour, then add 120 g (0.72 mol) of 3,5-dimethoxybenzaldehyde (CASNo: 120-14-9) dropwise, and stir at room temperature for 1 Hour. The progress of the reaction was monitored by TLC (petroleum ether V:ethyl acetate V=1:4). When the reaction was completed, keep stirring, and slowly add 4L of ice water, resulting in a large amount of precipitation. Ethyl acetate was added for extraction, the ethyl acetate layer was washed 3 times with water, and dried over anhydrous sodium sulfate. The organic layer was concentrated to dryness under reduced pressure to obtain a crude product as a pale yellow solid. The solid crude product was washed with petro...

Embodiment 3

[0037] Embodiment 3: the preparation of picatanol

[0038] Under nitrogen protection, 120.4 g (0.4 mol) of 3,4,3′,5′-tetramethoxystilbene was dissolved in anhydrous dichloromethane solution, and 601.4 g (0.85 mol) of boron tribromide was added dropwise. mol) of anhydrous dichloromethane solution, keep the temperature constant at -30°C, after the dropwise addition, stir at room temperature for 2 hours, and monitor the reaction progress by HPLC. When the reaction reached the end point, the stirring was continued, and 4L of ice water was slowly added, and a large amount of precipitation was precipitated. Suction filtration, wash the filter cake with water. The filter cake was dissolved in ethyl acetate and washed with water. The organic layer was concentrated to dryness under reduced pressure to obtain a pink solid crude product, which was stirred with ethyl acetate and petroleum ether, and a large amount of precipitation was precipitated, filtered, and the filter cake was wash...

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Abstract

According to the method for preparing piceatannol of the invention, a condensation reaction between 3,5-dimethoxy benzyl phosphoric acid diethyl ester and 3,5-dimethoxy benzaldehyde is carried out to generate 3,4,3',5'-tetramethoxy stilbene, with dimethyl formamide as a solvent and tert-butyl alcohol potassium as a catalyst; then 3,4,3',5'-tetramethoxy stilbene conducts a demethylating reaction to generate piceatannol, with dichloromethane as a solvent. The method for preparing piceatannol of the invention has a yield reaching 45-50%, which is raised substantially compared with a prior synthesis yield. In addition, the preparation method of the invention requires cheap and easily available raw materials, is simply operated and easily controlled; reactants related to a synthesis process are safe; and the prepared piceatannol has a high purity; therefore, the method can be widely applied to industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a method for preparing picatanol. Background technique [0002] Resveratrol is a phytoalexin with a stilbene structure, mainly derived from the dry rhizome and root of Polygonum cuspidatum Sieb.et Zucc., the skin and fruit of Vitis vinifera. Seeds, seeds of leguminous plant peanut (Arachis hypogaea) and other plants. Modern pharmacological studies have shown that resveratrol is a natural antioxidant that can reduce blood viscosity, inhibit platelet aggregation and vasodilation, keep blood flowing, and have anti-atherosclerosis, coronary heart disease and ischemic heart disease. sick. At the same time, resveratrol also has tumor-inhibiting and estrogen-like effects, which can prevent the occurrence and development of cancer and the treatment of breast cancer and other diseases. Therefore, resveratrol is a potential preventive anticancer drug. However, due to the photosensitiv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/50
Inventor 陈锦锌龚云麒方芳
Owner KPC PHARM INC
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