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Synthetic method of oxyresveratrol

A technology of oxystilbene triphenol and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of long synthesis route, high risk of operation, low total yield, etc. Short, less reaction steps, high yield effect

Inactive Publication Date: 2015-11-11
CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods have relatively long synthetic routes, relatively low total yields, and high operational risk.

Method used

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  • Synthetic method of oxyresveratrol

Examples

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Embodiment 1

[0016] Embodiment 1: the synthesis of oxystilbene triphenol

[0017] Add 0.014g lithium chloride, 0.200g tetrakis (triphenylphosphine) palladium, 0.324g potassium hydroxide, 0.880g 4-iodine resorcinol, 0.300g acrylic acid in sequence in a 50mL round bottom flask, then add 3mL distilled water, Heat and stir in an oil bath at 85°C for 3h. The reaction system was cooled to room temperature. Then add 0.005g lithium chloride, 0.145g tetrakis (triphenylphosphine) palladium, 0.900g 5-iodine resorcinol, 0.82mL piperidine, 12mL N,N -Dimethylacetamide, heating and reacting in an oil bath at 140°C for 14h. After the reaction was completed, the system was cooled to room temperature and filtered. Dilute hydrochloric acid was added to the filtrate to make it acidic (pH=5). Pour into a separatory funnel and extract with ethyl acetate (20mL*3). Combine the organic phases, dry the organic layer with anhydrous sodium sulfate, filter, and spin off the solvent. The crude product was purifie...

Embodiment 2

[0018] Embodiment 2: the synthesis of oxystilbene triphenol

[0019] Add 0.140g of lithium chloride, 2.000g of tetrakis(triphenylphosphine) palladium, 3.240g of potassium hydroxide, 8.800g of 4-iodoresorcinol, 3.000g of acrylic acid in sequence in a 500mL round bottom flask, and then add 30mL of distilled water. Heat and stir in an oil bath at 85°C for 3.5 hours. The reaction system was cooled to room temperature. Then add 0.050g lithium chloride, 1.450g tetrakis(triphenylphosphine) palladium, 9.000g 5-iodoresorcinol, 8.20mL piperidine, 120mL N,N -Dimethylacetamide, heating and reacting in an oil bath at 140° C. for 15 hours. After the reaction was completed, the system was cooled to room temperature and filtered. Dilute hydrochloric acid was added to the filtrate to make it acidic (pH=5). Pour into a separatory funnel and extract with ethyl acetate (200mL*3). Combine the organic phases, dry the organic layer with anhydrous sodium sulfate, filter, and spin off the solvent...

Embodiment 3

[0020] Embodiment 3: the synthesis of oxystilbene triphenol

[0021] Under the protection of nitrogen, add 0.014g lithium chloride, 0.200g tetrakis (triphenylphosphine) palladium, 0.324g potassium hydroxide, 0.880g 4-iodine resorcinol, 0.300g acrylic acid to a 50mL round bottom flask successively, and then add 3mL of distilled water was heated and stirred in an oil bath at 85°C for 3h. The reaction system was cooled to room temperature. Then add 0.005g lithium chloride, 0.145g tetrakis (triphenylphosphine) palladium, 0.900g 5-iodine resorcinol, 0.82mL piperidine, 12mL N,N -Dimethylacetamide, heating and reacting in an oil bath at 140°C for 14h. After the reaction was completed, the system was cooled to room temperature and filtered. Dilute hydrochloric acid was added to make the filtrate acidic (pH=5). Pour into a separatory funnel and extract with ethyl acetate (25mL*3). Combine the organic phases, dry the organic layer with anhydrous sodium sulfate, filter, and spin off...

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Abstract

The invention relates to a synthetic method of oxyresveratrol. The synthetic method specifically comprises the following steps: carrying out Heck reaction on 4-idodine m-dihydroxybenzene and acrylic acid under the action of a palladium catalyst; then carrying out decarboxylation to generate an intermediate 2, 4-dyhydroxyl styrene without purification; enabling the unpurified 2, 4-dyhydroxyl styrene and 5-idodine m-dihydroxybenzene to directly react under the action of the palladium catalyst to obtain the oxyresveratrol. The synthetic method is simple in raw materials, high in the operability of the reaction condition, few in steps, short in reaction time and high in yield.

Description

technical field [0001] The invention relates to a method for synthesizing stilbene compounds, in particular to a method for efficiently synthesizing oxystilbene triphenol. Background technique [0002] Oxystilbene, also known as oxidized resveratrol, English name Oxyresveratrol, E-2,3',4,5'-tetrahydroxystilbene, system name: 2,4,3',5'-tetrahydroxystilbene , CAS: 29700-22-9, is the 2'-hydroxylation derivative of polyhydroxy trans-styrene stilbinol, the color is light yellow, the shape is amorphous solid, melting point: 199~201℃, relative density: 1.468g / cm 3 , easy to absorb moisture, soluble in water, methanol, ethanol, propanol and other solvents. Existing studies have shown that oxystilbene triphenol has a high-efficiency inhibitory effect on tyrosinase activity and skin pigmentation, and can resist herpes, defend against viruses, reduce oxidation, protect nerves, and reduce cell apoptosis when cerebral ischemia occurs. effect. Because of the low toxicity and high wate...

Claims

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Application Information

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IPC IPC(8): C07C37/18C07C39/21
CPCC07C37/18C07C39/21
Inventor 李志伟李江胜王宇陈琳
Owner CHANGSHA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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