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Synthesis method of piceatannol

A technology of picetanol and synthetic method, which is applied in the field of chemical synthesis of natural product piceatanl, can solve the problems of low reaction temperature, difficult handling, high price, etc., and achieve high product yield, easy availability of raw materials, and easy operation easy effect

Active Publication Date: 2016-03-30
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Xiao Chunfen et al. used 3,5-dihydroxyphenylacetic acid as raw material to prepare picatanol through Perkin condensation and deacidification isomerization. The total yield was reported to be 55%, and copper powder and quinoline were decarboxylated at a high temperature of nearly 200 ° C. The present invention People repeat this process and find that the post-processing of this step is more difficult, and the yield is also far lower than the reported level. The main raw material 3,5-dimethoxyphenylacetic acid is not easy to buy in large quantities, so this method is not suitable for industrial production.
Patent CN102351658A only uses 3,5-dimethoxybenzyl diethyl phosphate and 3,4 dimethoxybenzaldehyde as two intermediates as starting materials to prepare piceatanol through a two-step reaction. In this invention It only mentions the preparation of the raw material 3,5-dimethoxybenzyl diethyl phosphate, without specific data support, boron tribromide is used in the demethylation step, which is expensive, and the reaction temperature is too low, etc. Adapt to industrial production

Method used

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  • Synthesis method of piceatannol
  • Synthesis method of piceatannol

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 1, Preparation of 3,5-dimethoxybenzyl chloride

[0024] Put 42g of 3,5 dimethoxybenzyl alcohol and 126ml of phosphorus oxychloride into a dry 500ml four-necked reaction flask, heat up and reflux for about 2 hours, TLC detection, the raw materials are basically reacted, pressurize and recover the solvent to 1 / 3 and cool down To 0-5°C, slowly add 150ml of water dropwise, after the addition is complete, stir at room temperature for 2h, filter, wash with water to neutralize, and dry under reduced pressure to obtain 45g of white solid with a yield of 96.7%.

[0025] 2. Preparation of Tetramethoxypitetanol

[0026] Into a dry 500ml four-necked reaction flask, put 37.2g of 3,5-dimethoxybenzyl chloride, 27g of trimethyl phosphite, 80ml of N,N-dimethylformamide, heat up and reflux for 4.5h, TLC detection, The starting material 3,5-dimethoxybenzyl chloride disappeared. Cool down to 5-10°C, add 29.8g of 28% methanolic sodium methoxide solution dropwise, keep stirring at this tem...

Embodiment 2

[0029] 1, Preparation of 3,5-dimethoxybenzyl chloride

[0030] Put 42g of 3,5 dimethoxybenzyl alcohol and 170ml of phosphorus oxychloride into a dry 500ml four-necked reaction flask, heat up and reflux for about 2 hours, TLC detection, the raw materials have basically reacted, pressurize and recover the solvent to 1 / 3 and cool down To 0-5°C, slowly add 180ml of water dropwise, after the addition is complete, stir at room temperature for 2h, filter, wash with water to neutralize, dry under reduced pressure to obtain 43.5g of white solid, yield 93.5%.

[0031] 2. Preparation of Tetramethoxypitetanol

[0032] In a dry 500ml four-necked reaction flask, put 37.2g of 3,5-dimethoxybenzyl chloride, 24.8g of trimethyl phosphite, and 120ml of N,N-dimethylformamide, heat up and reflux for 4 hours, and detect by TLC. The starting material 3,5-dimethoxybenzyl chloride disappeared. Cool down to 5-10°C, add 29.8g of 28% methanolic sodium methoxide solution dropwise, keep stirring at this t...

Embodiment 3

[0035] 1, Preparation of 3,5-dimethoxybenzyl chloride

[0036] Put 42g of 3,5 dimethoxybenzyl alcohol and 200ml of phosphorus oxychloride into a dry 500ml four-neck reaction flask, heat up and reflux for about 3 hours, TLC detection, the raw materials are basically reacted, pressurize and recover the solvent to 1 / 3 to cool down To 0-5°C, slowly add 200ml of water dropwise, after the addition is complete, stir at room temperature for 2h, filter, wash with water to neutralize, and dry under reduced pressure to obtain 43.4g of white solid with a yield of 94.5%.

[0037] 2. Preparation of Tetramethoxypitetanol

[0038] In a dry 500ml four-necked reaction flask, put 37.2g of 3,5-dimethoxybenzyl chloride, 29.7g of trimethyl phosphite, 80ml of N,N-dimethylformamide, heat up and reflux for 3.5h, and detect by TLC , the raw material 3,5-dimethoxybenzyl chloride disappeared. Cool down to 5-10°C, add dropwise 44g of 28% methanolic sodium methoxide solution, keep stirring at this temper...

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Abstract

The present invention provides a synthesis method of piceatannol. The method comprises the following steps: reacting 3,5-dimethoxybenzyl alcohol with phosphorus oxychloride to obtain 3,5-dimethoxybenzyl chloride; adding the obtained 3,5-dimethoxybenzyl chloride and trimethyl phosphite into a solvent such as N,N-dimethyl formamide, after the reaction is completed, adding 3,4-dimethoxybenzaldehyde and a catalyst such as a sodium methoxide solution to obtain tetramethoxy piceatannol; and dissolving the obtained tetramethoxy piceatannol in chlorobenzene, then adding triethylamine and anhydrous aluminum chloride to obtain the piceatannol. According to the method provided by the present invention, a Wittig-Horner reaction is adopted, the raw materials are easily available, and the cost is low; and the overall process flow is easy in operation and high in product yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a chemical synthesis method of natural product piceatanol. Background technique [0002] Picetanol (3, 3 ， ,4,5 ， -Tetrahydroxy-trans-stilbene, the English name is piceatannol), the 3-hydroxylation analogue of resveratrol, and piceatannol is found in grapes, rhubarb, blueberry, passion fruit, sugarcane and other plants. Pharmacological studies have shown that picatanol has many pharmacological activities, such as anti-cancer, anti-cell proliferation, anti-inflammation, immune regulation, anti-lipid oxidation, antibacterial and inhibition of H in the stomach. + 、K + , ATPase and other pharmacological activities. Studies have shown that the scavenging ability of picatanol to free radicals and superoxide anion is stronger than that of resveratrol, and it is also a good antioxidant and cardiovascular protective agent. With the continuous deepening of development, p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/055C07C39/21
CPCY02P20/584C07C37/055C07C41/30C07F9/4056C07C39/21C07C43/215
Inventor 肖金霞郭文华靳莎杨雪峰
Owner SHAANXI JIAHE PHYTOCHEM
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