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Method for preparing diphenyl ethylene compound through decarboxylic reaction

A technology of stilbenes and decarboxylation reaction, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of aminohydroxyl compounds. It can solve the problems of narrow substrate range, increased cost, and unrecoverable ligands, etc., and achieve saving Cost, convenient separation and purification, and wide range of substrate applications

Inactive Publication Date: 2013-02-13
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of the quinoline / copper powder decarboxylation system have not been fundamentally changed, and the ligands used cannot be recovered, which increases the cost (Chemical Bulletin, 2012, 75(6): 526-531)
(3) PEG / alkali or ionic liquid / alkali decarboxylation system: use 2,3-diaryl acrylic compound as raw material, add some organic base (such as methylimidazole) or inorganic base (such as sodium bicarbonate), in the ionic In liquid or PEG, stilbene compounds can be obtained after microwave irradiation for a long time; however, the substrate range of this method is narrow, and it can only decarboxylate 2,3-diaryl acrylic compounds with hydroxyl substitution at the 4-position of A ring , and only trans-stilbenes can be obtained (Adv.Synth.&Cat.2008, 350(18), 2910-2920)

Method used

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  • Method for preparing diphenyl ethylene compound through decarboxylic reaction
  • Method for preparing diphenyl ethylene compound through decarboxylic reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: (Z)-3,4,4', the preparation of 5-tetramethoxy-3'-aminostilbene

[0025] (E)-3-(3,4,5-trimethoxyphenyl)-2-(3'-amino-4'-methoxyphenyl)acrylic acid 1.795g (5mmol), cuprous iodide 0.0952 g (0.5mmol), o-phenanthroline 0.0991g (0.5mmol), PEG-40020mL were added to the reaction flask, and nitrogen protection was applied, and the reaction device was placed in a microwave synthesizer, and the power was set to 800W. The reaction was 6 minutes, and each reaction was 2 minutes. , intermittent 5min. After the reaction was completed, cool slightly, add 20mL of ice water and 20mL of ethyl acetate, filter with suction to obtain a brick red solid, rinse with distilled water 3 times, dry in the air, and recover. The filtrate was allowed to stand, and the ethyl acetate layer was separated, and the aqueous layer was extracted twice with ethyl acetate, 20 mL / time, the ethyl acetate layers were combined, dried with anhydrous magnesium sulfate, suction filtered, and concentrated...

Embodiment 2

[0027] Embodiment 2: (Z)-3,4,4', the preparation of 5-tetramethoxy-3'-aminostilbene

[0028] (E)-3-(3,4,5-trimethoxyphenyl)-2-(3'-amino-4'-methoxyphenyl)acrylic acid 1.795g (5mmol), recovered in Example 1 to obtain Cuprous iodide and o-phenanthroline complex 0.359g (20wt%), PEG-400 20mL is added in the reaction flask, feeds nitrogen protection, puts the reaction device into a microwave synthesizer, sets the power to 800W, and reacts for 8min. Each reaction is 2 minutes, and the interval is 5 minutes. Cool slightly after the reaction is complete, add 20mL ice water and 20mL ethyl acetate, filter with suction to obtain a brick red solid, rinse with distilled water 3 times, dry, recover, the filtrate is allowed to stand and the ethyl acetate layer is separated, and the water layer is then washed with acetic acid Ethyl extraction was performed twice, 20 mL each time, the ethyl acetate layers were combined, dried over anhydrous magnesium sulfate, suction filtered and concentrated ...

Embodiment 3

[0029] Example 3: Preparation of (E)-3,4,4',5-tetramethoxy-3'-aminostilbene

[0030] (Z)-3-(3,4,5-trimethoxyphenyl)-2-(3'-amino-4'-methoxyphenyl)acrylic acid 1.795g (5mmol), cuprous iodide 0.0952 g (0.5mmol), o-phenanthroline 0.0991g (0.5mmol), and PEG-40050mL were added to the reaction flask, and nitrogen protection was introduced, and the reaction device was placed in a microwave synthesizer, and the power was set at 800W, and the reaction was carried out for 6 minutes. 2min, intermittent 5min. Cool slightly after the reaction is complete, add 25ml of ice water and 25mL of ethyl acetate, filter with suction to obtain a brick red solid, rinse with distilled water 3 times, dry in the air, recover, let the filtrate stand still and separate the ethyl acetate layer, the water layer is then washed with acetic acid Ethyl extraction was carried out twice, 25 mL each time, the ethyl acetate layers were combined, dried over anhydrous magnesium sulfate, suction filtered and concentrat...

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Abstract

The invention discloses a method for preparing a diphenyl ethylene compound through a decarboxylic reaction. The method comprises the following steps of: performing a microwave radiation reaction on a 2,3-diaryl acrylic acid compound in polyethylene glycol by taking cuprous iodide and phenanthroline as catalysts; and purifying to obtain a diphenyl ethylenes compound. A substrate used in the method has the advantages of wide application range, predictability of the cis-trans configurations of raw materials, simple process, environment friendliness, low cost and high yield.

Description

technical field [0001] The invention relates to the field of chemical industry and medicine, in particular to a method for preparing stilbene compounds through decarboxylation reaction. Background technique [0002] Stilbene natural products and their derivatives have good biological activity, and their scientific research value and application prospects as pharmaceutical products have attracted great attention. The stilbene compounds are mainly divided into two categories: one is trans-stilbene compounds represented by resveratrol, pterostilbene, albinol, etc., which can activate Sirtuins anti-aging enzymes, prevent cancer and fight cancer , antibacterial and anti-inflammatory, hypoglycemic and lipid-lowering, neuroprotective and other beneficial physiological activities and therapeutic and health effects; the other is cis-stilbene compounds represented by vascular blockers (VDA, Vascular Disrupting Agents), such as CA-4, CA-1, AVE8062, etc., can inhibit tubulin polymeriza...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C217/80C07C41/18C07C43/23C07C43/225C07C43/215
Inventor 邹永黄琦黄桐堃魏文徐田龙张恩生吕泽良
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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