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Method for preparing resveratrol and derivative of resveratrol

A technology of resveratrol and its derivatives, applied in the field of phytochemistry, can solve the problems of poor selectivity, harsh reaction conditions, cumbersome steps, etc., and achieve the effect of good stereoselectivity and mild conditions

Inactive Publication Date: 2015-03-25
GUANGXI UNIV FOR NATITIES
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] 4. In addition, Zhu Yehong (CN 103214352, 2013.07.24) also disclosed a method for preparing resveratrol and its analogs by solid base catalysis of composite metal oxides, but the preparation cost of composite metal oxides is high, and it is not suitable for industrialization
[0011] There are many disadvantages in the above methods, such as low yield, poor selectivity, cumbersome steps, high cost of raw materials, harsh reaction conditions, etc.

Method used

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  • Method for preparing resveratrol and derivative of resveratrol
  • Method for preparing resveratrol and derivative of resveratrol
  • Method for preparing resveratrol and derivative of resveratrol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: Preparation of resveratrol (trans-3,5,4'-trihydroxystilbene): (m=1)

[0037]

[0038] 1.Corey-Fuchs reaction: Synthesis of 1,1-dibromo-3′,5′-dimethoxystyrene

[0039]Get carbon tetrabromide (10.5g, 31mmol) and join in clean and dry 250mL reaction bottle, add the organic solvent methylene chloride of 100mL, add triphenylphosphine (16.4g, 62mmol) and 3,5-dimethoxy Benzaldehyde (2.5g, 15mmol) reacted completely under stirring at room temperature-20°C. After separation and drying, 4.5g of white solid was obtained with a yield of 92.7%.

[0040] The molar ratio of 3,5-dimethoxybenzaldehyde: carbon tetrabromide: triphenylphosphine is = 1: 2.06: 4.13

[0041] MP:73.7-74.5℃;IR(KBr):2997,1600,1456,1417,1337,1143,879,816,676,629cm -1 . 1 HNMR (CDCl 3 ): δ3.79(s,6H),6.45(t,J=2.3Hz,1H),6.68(dd,J=2.3Hz,2H),7.42(s,1H)ppm.

[0042] 2. Reduction reaction: Synthesis of 1-bromo-3′,5′-dimethoxystyrene

[0043] In a dry 100mL flask, add 1,1-dibromo-3′,5′-dimethoxysty...

Embodiment 2

[0053] Example 2: Preparation of Compound 2 (trans 3,5,2',4'-tetrahydroxystilbene): (m=2)

[0054]

[0055] 1.Corey-Fuchs reaction: Synthesis of 1,1-dibromo-3′,5′-dimethoxystyrene

[0056] Take carbon tetrabromide (10.5g, 31mmoL) and add it to a clean and dry 250mL reaction flask, add 100mL of organic solvent methylene chloride, add triphenylphosphine (16.4g, 62mmol) and 3,5-dimethoxy Benzaldehyde (2.5g, 15mmol) reacted completely under stirring at room temperature 20°C. After separation and drying, 4.5g of white solid was obtained with a yield of 92.7%.

[0057] The molar ratio of 3,5-dimethoxybenzaldehyde: carbon tetrabromide: triphenylphosphine is = 1: 2.06: 4.13

[0058] MP:73.7-74.5℃;IR(KBr):2997,1600,1456,1417,1337,1143,879,816,676,629cm -1 . 1 HNMR (CDCl 3 ): δ3.79(s,6H),6.45(t,J=2.3Hz,1H),6.68(dd,J=2.3Hz,2H),7.42(s,1H)ppm.

[0059] 2. Reduction reaction: Synthesis of 1-bromo-3′,5′-dimethoxystyrene

[0060] In a dry 100mL flask, add 1,1-dibromo-3′,5′-dimethoxys...

Embodiment 3

[0069] Example 3: Preparation of compound 3 (trans 3,5,3',4'-tetrahydroxystilbene): (m=2)

[0070]

[0071] 1.Corey-Fuchs reaction: Synthesis of 1,1-dibromo-3′,5′-dimethoxystyrene

[0072] Take carbon tetrabromide (5.3g, 15.5mmol) and join in a clean and dry 100mL reaction flask, add 30mL of chloroform, add triphenylphosphine (8.2g, 31mmol) and 3,5-dimethoxybenzene Formaldehyde (1.3g, 7.8mmol) was stirred and reacted at room temperature at 40°C. After complete separation and drying, 2.3g of white solid was obtained with a yield of 93%.

[0073]The molar ratio of 3,5-dimethoxybenzaldehyde: carbon tetrabromide: triphenylphosphine is =1:2:0.5.

[0074] MP:73.7-74.5℃;IR(KBr):2997,1600,1456,1417,1337,1143,879,816,676,629cm -1 . 1 HNMR (CDCl 3 ): δ3.79(s,6H),6.45(t,J=2.3Hz,1H),6.68(dd,J=2.3Hz,2H),7.42(s,1H)ppm.

[0075] 2. Reduction reaction: Synthesis of 1-bromo-3′,5′-dimethoxystyrene

[0076] In a dry 100 mL flask, add 1,1-dibromo-3′,5′-dimethoxystyrene (3 g, 9.2 mmol), a...

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Abstract

The invention discloses a method for preparing resveratrol and derivatives of resveratrol. The method comprises the following steps: by taking an aromatic aldehyde derivative I as a raw material, performing Corey-Fuchs reaction so as to prepare a middle product 1,1-bromostyrene derivative; performing reduction reaction on the middle product 1,1-bromostyrene derivative so as to prepare a middle product trans-1-bromostyrene derivative; further by taking the middle product trans-1-bromostyrene derivative as a raw material, adding arylboronic acid, and performing Suzuki reaction so as to prepare resveratrol analogs 4, 5, 6 and 7; and performing deprotection reaction so as to obtain resveratrol 1 and analogs 3 and 4 of resveratrol. The method is gentle in reaction condition, high in yield, environmentally friendly, very high in stereoselectivity and good in industrialization production prospect.

Description

technical field [0001] The invention belongs to the field of phytochemistry, and in particular relates to a method for preparing resveratrol and its derivatives by Suzuki reaction without ligand. Background technique [0002] Resveratrol (trans-3,5,4'-trihydroxystilbene, Reveratrol), the chemical structure is as follows: [0003] [0004] Widely present in more than 70 different plants (such as grapes, peanuts, resveratrol, etc.), which are regularly consumed by humans. The attention to resveratrol began with epidemiological studies showing an inverse relationship between drinking red wine and coronary heart disease, the so-called French paradox. In the past few decades, the biological activity of resveratrol has attracted great attention of researchers and has been studied in depth. [0005] Years of physiological and pathological studies have shown that resveratrol has anti-oxidation, anti-mutation, anti-tumor, anti-inflammatory, anti-aging, scavenging free radicals, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/21C07C37/055C07C43/23C07C43/215C07C41/30
CPCC07C41/30C07C37/055C07C41/24C07C43/225C07C43/215C07C39/21C07C43/23
Inventor 吴爱群申利群唐勇姚兴东雷福厚陈其锋
Owner GUANGXI UNIV FOR NATITIES
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