Synthesis method of natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene

A technology of tetrahydroxystilbene and natural products, applied in the direction of organic chemical methods, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of difficult acquisition of raw materials, difficult large-scale preparation, poor atom economy, etc., and achieve reaction Environmentally friendly conditions, high yield, and easy operation

Active Publication Date: 2017-05-31
GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK +1
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Regarding the synthesis of E-2,3',4,5'-tetrahydroxystilbene, there are Wittig reaction, Wittig-Horner reaction, Suzuki cross-coupling reaction and Perkin condensation reaction methods etc. in bibliographical reports, but these methods have high cost, Noble metal catalyst is required, the yield is low, the raw materials are not easy to obtain, and the hydroxyl group needs to be protected by methyl, silyl, etc. and then deprotected (Chem.Pharm.Bull.2010,58,1492-1496; Chin.J.Org.Chem.,2010 , 30, 1574-1579; Eur.J.Med.Chem., 2007, 42, 841-850; Bioorg.Med.Chem.Lett., 2006, 16, 5767-5772), poor atom economy, difficulty in large-scale preparation, etc.

Method used

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  • Synthesis method of natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene
  • Synthesis method of natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene
  • Synthesis method of natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene

Examples

Experimental program
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Effect test

Embodiment 1

[0033] (1) Preparation of 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester

[0034] Put 1,3-acetonedicarboxylate dimethyl (24.36g, 140mmol) into a single-necked round bottom flask, and then throw in metallic sodium (0.28g, 12mmol), and stir overnight at room temperature. Heated to 140°C, distilled, and reacted for 3h. After the reaction is completed, wash with water and filter with suction to obtain a yellow powder solid, dry it, and recrystallize it with acetone to obtain a light yellow solid, which is methyl 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetate, weighing 19.74g , yield 95%.

[0035] (2) Preparation of 3,5-dihydroxyphenylacetic acid

[0036] Add 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester (7.15g, 24mmol) into the round bottom flask, then pour 12% sodium hydroxide aqueous solution (64ml, 192mmol), and heat in an oil bath Distill at 140°C for 3h, after the reaction, cool to 80°C, add concentrated sulfuric acid (33.6ml, 240mm...

Embodiment 2

[0042] (1) Preparation of 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester

[0043] Put 1,3-acetonedicarboxylate dimethyl (24.36g, 140mmol) into a single-necked round bottom flask, and then throw in metallic sodium (0.28g, 12mmol), and stir overnight at room temperature. Heated to 140°C, distilled, and reacted for 3h. After the reaction is completed, wash with water and filter with suction to obtain a yellow powder solid, dry it, and recrystallize it with acetone to obtain a light yellow solid, which is methyl 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetate, weight 19.02g , yield 91%.

[0044] (2) Preparation of 3,5-dihydroxyphenylacetic acid

[0045] Add 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester (7.15g, 24mmol) into the round bottom flask, then pour 12% potassium hydroxide aqueous solution (56ml, 120mmol), and heat in an oil bath Distill at 140°C for 3h. After the reaction, cool to 80°C, add concentrated sulfuric acid (26.9ml, 192m...

Embodiment 3

[0051] (1) Preparation of 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetic acid methyl ester

[0052] Add 60ml of methanol, sodium metal (0.28g, 12mmol) and dimethyl 1,3-acetonedicarboxylate (24.36g, 140mmol) into a single-necked round bottom flask, and stir overnight at room temperature. Heated to 140°C, distilled, and reacted for 3h. After the reaction is completed, wash with water and filter with suction to obtain a yellow powder solid, dry it, and recrystallize it with acetone to obtain a light yellow solid, which is methyl 3,5-dihydroxy-2,4-dimethoxycarbonylphenylacetate, weight 10.90g , yield 52%.

[0053] (2) Preparation of 3,5-dihydroxyphenylacetic acid

[0054] Drop into 3,5-dihydroxy-2,4-dimethoxycarbonyl phenylacetic acid methyl ester (7.15g, 24mmol) in the round bottom flask, then pour cesium hydroxide (30g, 0.2mol), water (70ml), Heat in an oil bath at 140°C for distillation for 3 hours. After the reaction is complete, cool to 80°C, add concentrated sulfuric aci...

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Abstract

The invention discloses a synthesis method of a natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene. According to the method, 1,3-acetone dicarboxylic acid dimethyl ester is used as a starting raw material; condensation and aromatization reactions are performed to obtain 3,5-dihydroxy-2,4-dicarboxylate methyl phenyl acetate; then, hydrolysis and decarboxylation are performed to obtain 3,5-dyhydroxy phenylacetic acid; the 3,5-dyhydroxy phenylacetic acid and 2,4-dihydroxy benzaldehyde take condensation reaction under the existence of alkali to obtain 3-(3,5-dihydroxy phenyl)-7-hydroxy coumarin; next, open loop decarboxylation reaction is performed under the alkaline condition; the natural product of E-2,3',4,5'-tetrahydroxy diphenyl ethylene is obtained. The method has the advantages that the raw materials are easily obtained; the reaction route is simple and fast; the operation is convenient; the yield is higher.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing natural product E-2,3',4,5'-tetrahydroxystilbene. Background technique [0002] E-2,3',4,5'-Tetrahydroxystilbene (Oxyresveratrol) is a natural product isolated for the first time from Yunnan jackfruit (Artocarpus lakoocha). It is also found in Liliaceae, Liliaceae, and Gnetaceae, and is the 2'-hydroxylated derivative of the important stilbene natural product resveratrol. E-2,3',4,5'-Tetrahydroxystilbene has a variety of beneficial biological activities, such as Tyrosinase inhibition, Antioxidant, Neuroprotective, anti-inflammatory Anti-inflammatory, Hepatoprotective, Antibrowning and Anti-allergic (Bioorg.Med.Chem.Lett., 2006, 16, 5650-5653; Chem. Biol. Interact., 2016, 245, 110-121; Nitric Oxide., 2003, 9, 64-76; Biol. Pharm. Bull., 2006, 29, 2419-2424; J. Agric. Food. Chem., 2008, 56 , 4463-4468; Environ. Toxicol. Pharmacol., 2008, 26, 325-330; Arch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/50C07C39/21C07D311/16C07C67/343C07C69/84C07C27/02C07C51/38C07C59/52
CPCC07C37/50C07C51/09C07C51/38C07C67/343C07D311/16C07B2200/09
Inventor 邹永黄熙华盛剑飞宋现恒位文涛
Owner GUANGZHOU ZHONGDA NANSHA TECH INNOVATION IND PARK
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