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Flavonone compound synthesized through one-pot process and preparation method thereof

A technology of dihydroflavones and compounds, which is applied in the field of synthesis of flavone derivatives, can solve problems such as many steps, difficult conditions, and insufficient production capacity, and achieve the effects of mild reaction conditions, reduced use of harmful solvents, and reduced emissions

Inactive Publication Date: 2017-10-24
无锡紫杉药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The current industrial production of dihydroflavonol mainly comes from the extraction of plants. Due to the influence of a series of external conditions such as seasons and places of production, there will be insufficient production capacity.
However, the traditional chemical synthesis method of dihydroflavonol has many steps, and each step requires purification and separation, which makes the conditions for industrial production more difficult

Method used

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  • Flavonone compound synthesized through one-pot process and preparation method thereof
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  • Flavonone compound synthesized through one-pot process and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] refer to figure 1 , a preparation method of said 3',4',5,7-tetrahydroxydihydroflavone (taxifolin), said preparation method comprising the following specific steps:

[0025] (1) Dissolve 10g of 2,4,6-trihydroxyacetophenone and 8.2g of 3,4-dihydroxybenzaldehyde in 100mL of anhydrous tetrahydrofuran, then add 36g of chloromethyl methyl ether and 18g of 60% sodium hydride , reacted at 5°C for 2h, then added 6.0mL of 1.0mol / L sodium hydroxide aqueous solution to the reaction solution, and condensed at 25°C for 4h to obtain intermediate 3;

[0026] (2) Add 6.8 mL of 30% hydrogen peroxide to the reaction liquid containing intermediate 3 prepared in step (1), and react at 25° C. for 4 hours to obtain intermediate 4;

[0027] (3) Charge hydrogen chloride gas into the reaction solution containing intermediate 4 obtained through step (2), control the temperature at 55° C., stop charging HCl gas when the pH in the reaction solution is less than 1, and continue the reaction for 30 ...

Embodiment 2

[0032] refer to figure 1 , a preparation method of the 2', 5'-dimethoxy-5,7-dihydroxyflavone, the preparation method comprising the following specific steps:

[0033] (1) Dissolve 10g of 2,4,6-trihydroxyacetophenone and 9.9g of 2,5-dimethoxybenzaldehyde in anhydrous tetrahydrofuran, then add 21.6g of chloromethyl methyl ether and 10.7g of 60% Sodium hydride, react at 5°C for 2h, then add 6.0mL of 1.0mol / L sodium hydroxide aqueous solution to the reaction solution, and condense at 25°C for 4h to obtain intermediate 3;

[0034] (2) Add 6.8 mL of 30% hydrogen peroxide to the reaction liquid containing intermediate 3 prepared in step (1), and react at 25° C. for 4 hours to obtain intermediate 4;

[0035] (3) Charge hydrogen chloride gas into the reaction solution containing intermediate 4 obtained through step (2), control the temperature at 55° C., stop charging HCl gas when the pH in the reaction solution is less than 1, and continue the reaction for 30 minutes , and finally a...

Embodiment 3

[0040] refer to figure 1 , a preparation method of said 2', 3', 5-trihydroxyflavones, said preparation method comprising the following specific steps:

[0041] (1) Dissolve 10g of 2,6-dihydroxyacetophenone and 9.1g of 2,3-dihydroxybenzaldehyde in 100mL of anhydrous tetrahydrofuran, then add 31.8g of chloromethyl methyl ether and 22.4g of 60% sodium hydride , reacted at 5°C for 2h, then added 6.6mL of 1.0mol / L sodium hydroxide aqueous solution to the reaction solution, and condensed at 25°C for 4h to obtain intermediate 3;

[0042] (2) Add 7.4 mL of 30% hydrogen peroxide to the reaction liquid containing intermediate 3 prepared in step (1), and react at 25° C. for 4 hours to obtain intermediate 4;

[0043] (3) Charge hydrogen chloride gas into the reaction solution containing intermediate 4 obtained through step (2), control the temperature at 55° C., stop charging HCl gas when the pH in the reaction solution is less than 1, and continue the reaction for 30 minutes , finally ...

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Abstract

The invention discloses a flavonone compound synthesized through one-pot process and a preparation method thereof. The preparation method includes following steps: (1), using 2-hydroxyacetophenone compound and benzaldehyde compound as initial raw materials to prepare an intermediate 3 under joint action of chloromethyl methyl ether, sodium hydride and sodium hydroxide water solution; (2), adding hydrogen peroxide of 30% to obtain an intermediate 4; (3), feeding hydrogen chloride gas into reaction liquid, adding water and ethyl acetate for extraction after reaction is finished, drying and concentrating an organic phase, and passing a silica gel column for purifying to obtain the flavonone compound. The preparation method is mild in synthesis condition, unitary in reagent and solvent and simple in operation, treatment and purification of each reaction step are omitted, solvent consumption is lowered, and labor cost and time cost are reduced.

Description

technical field [0001] The invention relates to the technical field of synthesis of flavonoid derivatives, in particular to a method for synthesizing a dihydroflavonol racemate compound through a one-pot method. Background technique [0002] Dihydroflavonols are ubiquitous in plants. Research in recent years has found that dihydroflavonols not only have strong antioxidant and anti-inflammatory effects, but also have anti-cancer, antibacterial, and anti-allergic effects. Taxifolin, for example, is an essential antioxidant mainly extracted from the roots of larch in the alpine zone. According to the 2006 edition of the Russian Pharmacopoeia, it has the functions of anti-oxidation, enhancing immunity, anti-tumor, preventing cardiovascular disease, balancing blood lipids, detoxifying and protecting the liver, improving the stomach, and whitening the skin. Because dihydroflavonol has a broad spectrum of biological activity and pharmacological effects, it is an important raw mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32A61P29/00A61P39/06
CPCC07D311/32
Inventor 蒋文君章莎莎葛月兰汤伟彬
Owner 无锡紫杉药业股份有限公司
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