Method for synthesizing pterostilbene and derivatives thereof

The technology of a derivative and pterostilbene is applied in the synthesis field of pterostilbene and its derivatives, and can solve the problems of complicated steps, low yield, unsuitable large-scale production of pterostilbene and its derivatives, etc., and achieves simple steps and high yield. high effect

Active Publication Date: 2016-03-02
HUNAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing synthetic method steps are relatively complicated, and the yield is low, which is not suitable for the large-scale production of pterostilbene and its derivatives.

Method used

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  • Method for synthesizing pterostilbene and derivatives thereof
  • Method for synthesizing pterostilbene and derivatives thereof
  • Method for synthesizing pterostilbene and derivatives thereof

Examples

Experimental program
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Embodiment

[0026] 7.61mmol of 3,5-dimethoxybromobenzene, 7.61mmol of 3,5-dimethoxycinnamic acid, Cs 2 CO 3 9.14mmol, 1,10-phenanthroline 0.457mmol, triphenylphosphine 0.457mmol, CuCl 1.142mmol, Pd(acac) 2 0.228mmol, then add 7.6ml of reaction solvent N-methyl-1,2-pyrrolidone, and reflux reaction for 3h under the condition of silicone oil bath at about 140°C to obtain the reactant;

[0027] The resulting reactant was lowered to room temperature, extracted with water-dichloroethane with a volume ratio of 1:2, separated, and the organic layer was set aside, and dichloromethane was added to the obtained water layer for extraction, separated, and the organic layer obtained by the two extractions was separated. Combined, anhydrous MgSO 4 Dry, concentrate, and use flash column chromatography (stationary phase is 230-400 mesh silica gel, mobile phase is 10-20% diethyl ether n-hexane solution) to carry out purification, collect the first band, that is, the exo configuration product, and collect...

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Abstract

The present invention relates to a method for synthesizing pterostilbene and derivatives thereof. The method comprises the steps of: by using cinnamic acid derivatives as a raw material, carrying out a reaction with Cu+ under a Cs catalytic condition to generate an intermediate styryl copper; and carrying out an Heck decarboxylation coupling reaction on the intermediate with 3, 5-dimethoxy bromobenzene under a Pd catalytic condition to generate pterostilbene and derivatives thereof. The method provided by the present invention is simple in step, high in yield and suitable for large-scale synthesis of pterostilbene and derivatives thereof.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a synthesis method of pterostilbene and its derivatives. Background technique [0002] Pterostilbene, 3,5-dimethoxy-4'-hydroxystilbene, was first extracted and isolated from Pterostilbene in 1941, and later found to be widely present in a series of natural products such as grapes and berries, including common traditional family medicine. [0003] The stilbene compounds represented by pterostilbene and resveratrol are important biologically active substances. Dimers constructed by some structural units in this type of stilbene have different biological activities, among which pterostilbene and resveratrol have Anti-cancer, induction of PPAR-α, anti-oxidation, anti-inflammation, antibacterial, anti-platelet aggregation, expansion of blood vessels and other beneficial activities for health. [0004] At present, pterostilbene is mostly synthesized from 3,5-dimethoxybenzyl bromide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30C07C43/23C07C43/215C07C43/225C07C201/12C07C205/35
CPCC07C41/30C07C201/12C07C43/23C07C43/215C07C43/225C07C205/35
Inventor 王炜伊可拉斯·可汗阿玛·敕提波依纳盛文兵江星明彭彩云李斌黄建华翦雨青蔡雄
Owner HUNAN UNIV OF CHINESE MEDICINE
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