Novel method for preparing resveratrol and derivative thereof through decarbonylation heck reaction

A technology of resveratrol and derivatives, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problem of high cost and unfavorable preparation of three-substituted resveratrol resveratrol , difficult to obtain and other issues

Active Publication Date: 2011-05-11
CHINA RESOURCES SAIKE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, through a large number of experimental studies on the heck reaction such as Audurs, it was found that the cost of p-substituent styrene in this reaction is relatively high, and it is not easy to obtain, which is not conducive to the preparation of three-substituent resveratrol and then to obtain resveratrol

Method used

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  • Novel method for preparing resveratrol and derivative thereof through decarbonylation heck reaction
  • Novel method for preparing resveratrol and derivative thereof through decarbonylation heck reaction
  • Novel method for preparing resveratrol and derivative thereof through decarbonylation heck reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]

[0045] 1.1 3,5-dibenzyloxy-4 Synthesis of ′-methoxystilbene

[0046] In a 1000ml reaction flask, add 200ml of p-xylene and 20ml of N-methylmorpholine, then 31.6g of 3,5-dibenzyloxystyrene and 18.0g of p-methoxybenzoyl chloride, then add 0.15g of palladium acetate and 0.3g of N,N'-bis(2,6-diisopropylphenyl)imidazolium chloride, stirred well, raised the temperature to 120°C, and reacted for 4h under the protection of nitrogen. After the reaction was completed, cool to room temperature, filter, and the resulting filtrate was washed twice with 300ml of 5% sodium carbonate solution, then the organic layer was dried with anhydrous magnesium sulfate, filtered, concentrated to recover the solvent, and then recrystallized by adding 100ml of ethanol to obtain 34.2g 3,5-dibenzyloxy-4 '-Methoxystilbene, melting point 94-96°C, yield 81%.

[0047] 1.2 Preparation of 3,4′,5-trihydroxystilbene (resveratrol)

[0048] Take 21.1g 3,5-dibenzyloxy-4 '-Methoxystilbene, be dissolv...

Embodiment 2

[0050]

[0051] 2.1 3，-4 ', Synthesis of 5-trimethoxystilbene

[0052] In a 1000ml reaction flask, add 150ml of p-xylene and 20ml of N-methylmorpholine, then 16.4g of 3,5-dimethoxystyrene and 19.0g of p-methoxybenzoyl chloride, then add 0.15g of palladium acetate and 0.3g of N,N'-bis(2,6-diisopropylphenyl)imidazolium chloride, stirred well, raised the temperature to 100°C, and reacted for 4h under the protection of nitrogen. After completion of the reaction, cool to room temperature, filter, and the resulting filtrate is washed twice with 200ml of 5% sodium carbonate solution, then the organic layer is dried with anhydrous magnesium sulfate, filtered, concentrated to recover the solvent, and then recrystallized by adding 40ml of acetone to obtain 21.0g 3，-4 ', 5-trimethoxystilbene, melting point 56-57°C, yield 78%.

[0053] 2.2 Preparation of 3,4′,5-trihydroxystilbene (resveratrol)

[0054] Other conditions are the same as example 1.2, will 3,5-dibenzyloxy-4 '-Methoxys...

Embodiment 3

[0056]

[0057] 3.1 Synthesis of 3,5-dimethoxy-4′-acetoxystilbene

[0058] In a 1000ml reaction flask, add 150ml of p-xylene and 20ml of N-methylmorpholine, then 16.4g of 3,5-dimethoxystyrene and 22.0g of p-acetoxybenzoyl chloride, then add 0.15g of palladium acetate and 0.3 g N,N'-bis(2,6-diisopropylphenyl)imidazolium chloride, stir well, raise the temperature to 120-130°C, and react for 12h under the protection of nitrogen. After the reaction was completed, cool to room temperature, filter, and the resulting filtrate was washed twice with 200ml of 5% sodium carbonate solution, then the organic layer was dried with anhydrous magnesium sulfate, filtered, concentrated to recover the solvent, and then recrystallized by adding 20% ​​ethanol water to obtain 24.4 g 3,5-dimethoxy-4'-acetoxystilbene, yield 82%.

[0059] 3.2 Synthesis of 3,5-dimethoxy-4′-hydroxystilbene

[0060] 15g of 3,5-dimethoxy-4'-acetoxystilbene was dissolved in 80ml of tetrahydrofuran, 30ml of water and 40...

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Abstract

The invention relates to a novel method for preparing resveratrol and a derivative thereof through decarbonylation heck reaction. The method comprise the following steps: the raw material is soaked in a solution of organic solvent and organic base and then added with palladium catalyst and ligand; the temperature is gradually risen to be suitable for reaction; after the reaction, a trisubstitutedresveratrol derivative II is obtained through cooling, filtering, alkaline cleaning, drying and refining; and then the resveratrol is obtained by means of a suitable hydrolysis method.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and relates to a new method for preparing resveratrol and its derivatives, in particular to a new method for preparing resveratrol and its derivatives by decarbonylation heck reaction. Background technique [0002] Resveratrol (Reveratrol), the chemical name is trans-3, 4', 5-trihydroxystilbene (trans-3, 4', 5-trihydroxystilbene), is a stilbene that exists in plants Structured non-flavonoid natural polyphenolic compounds, the chemical structural formula of which is shown below: [0003] [0004] Resveratrol is a polyphenolic compound that is hormone It has obvious preventive effect on dependent tumors (including breast cancer, prostate cancer, endometrial cancer and ovarian cancer, etc.). OK Osteoporosis , acne (acne) and Alzheimer's disease preventive, has disease resistance Toxic and immunomodulatory effects. It has been widely used in the fields of medicine, health pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30C07C43/215C07C43/23C07C69/18C07C67/293C07C39/21C07C37/055
Inventor 刘沫毅李志强
Owner CHINA RESOURCES SAIKE PHARMA
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