Pinocembrin synthesis method

A synthesis method and technology for chosone, applied in the field of chemical synthesis, can solve the problems of high cost, low yield, complicated synthesis process and the like, and achieve the effects of low cost, high yield and simple process

Inactive Publication Date: 2016-12-14
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the invention of the present invention is to provide a kind of synthetic method of pinocin, which mainly solves the problems of cumbersome synthetic process, low yield and high cost in the prior art.

Method used

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Examples

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Effect test

Embodiment 1

[0023] 1. Preparation of 2,4,6-trihydroxyacetophenone

[0024] In a 500 ml three-necked flask equipped with a magnetic electric stirrer, 50 g of anhydrous phloroglucinol and 52 ml of acetonitrile were added. Start the electromagnetic stirrer at normal temperature and stir thoroughly for one hour, then start to add 52 milliliters of phosphorus oxychloride dropwise, and the dropwise addition is completed in 2 hours. Then continue to stir, react for 6h, and place overnight. Slowly pour the reaction solution into 200 ml of water, reflux for 2 hours, add 2 g of activated carbon and continue to reflux for 30 minutes, and filter while hot. The filtrate was cooled and placed for 24h, and crystals were precipitated. Suction filtration, filter cake drying. 54 g of yellow needle-shaped product was obtained.

[0025] 2. Synthesis of jojosin

[0026] Add 54 grams of 2,4,6-trihydroxyacetophenone, 35 grams of benzaldehyde, 1 gram of L-proline and 100 milliliters of DMF into a 500 millil...

Embodiment 2

[0030] 1. Preparation of 2,4,6-trihydroxyacetophenone

[0031] In a 50 ml three-necked flask equipped with a magnetic electric stirrer, 25 g of anhydrous phloroglucinol and 26 ml of acetonitrile were added. Start the electromagnetic stirrer at normal temperature and stir thoroughly for one hour, then start to add 26 ml of phosphorus oxychloride dropwise, and the dropwise addition is completed in 2 hours. Then continue to stir, react for 6h, and place overnight. Slowly pour the reaction solution into 100 ml of water, reflux for 2 hours, add 2 g of activated carbon and continue to reflux for 30 minutes, and filter while hot. The filtrate was cooled and placed for 24h, and crystals were precipitated. Suction filtration, filter cake drying. 26 g of yellow needle-like product was obtained.

[0032] 2. Synthesis of jojosin

[0033] Add 27 grams of 2,4,6-trihydroxyacetophenone, 18 grams of benzaldehyde, 0.6 grams of L-proline and 60 milliliters of DMF into a 500 milliliter three...

Embodiment 3

[0037] 1. Preparation of 2,4,6-trihydroxyacetophenone

[0038] In a 500 ml three-necked flask equipped with a magnetic electric stirrer, 38 g of anhydrous phloroglucinol and 39 ml of acetonitrile were added. Start the electromagnetic stirrer at normal temperature and stir thoroughly for one hour, then start to add 39 ml of phosphorus oxychloride dropwise, and the dropwise addition is completed in 2 hours. Then continue to stir, react for 6h, and place overnight. Slowly pour the reaction solution into 300 ml of water, reflux for 2 hours, add 2 g of activated carbon and continue to reflux for 30 minutes, and filter while hot. The filtrate was cooled and placed for 24h, and crystals were precipitated. Suction filtration, filter cake drying. 39 g of yellow needle-shaped product was obtained.

[0039] 2. Synthesis of jojosin

[0040] Add 39 grams of 2,4,6-trihydroxyacetophenone, 27 grams of benzaldehyde, 0.75 grams of L-proline and 80 milliliters of DMF into a 500 milliliter t...

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Abstract

The invention provides a pinocembrin synthesis method. The method comprises the following steps that under the room temperature condition, phloroglucinol and acetonitrile are stirred to be uniform, phosphorus oxychloride is added for a reaction, and 2,4,6-trihydroxyacetophenone is obtained; under the catalytic action of a catalyst L-proline, obtained 2,4,6-trihydroxyacetophenone and benzaldehyde are subjected to a ring closing reaction in DMF, and a crude pinocembrin product is obtained; the obtained crude pinocembrin product is subjected to recrystallization with ethyl alcohol, activated carbon is adopted for decolourization, and the pinocembrin is obtained. The synthesis method is simple in technology, low in cost, capable of saving time, high in yield and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing pinocetine. Background technique [0002] Qiaopinin, also known as squirrelin, is a dihydroflavone that exists in a variety of plants. Dihydroflavone, also known as flavanone, is a kind of flavonoids, distributed in Rosaceae, Rutaceae, Zingiberaceae, Compositae, Rhododendron, Fabaceae and other angiosperms. [0003] The structural formula of Qiao Songsu is as follows: [0004] [0005] Dihydroflavonoids have many biological activities such as sterilization, anti-inflammation, anti-tumor, anti-HIV virus, anti-mutagenesis, and anti-oxidation, and are a class of compounds with high research value. Most natural flavonoids have hydroxyl, isopentenyl, benzyloxy, methoxy, geranyl and other substituents. In addition, flavone has as many as 10 modifiable sites, which makes it have great potential for structural modification. Chopinin exists in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32
CPCC07D311/32
Inventor 郭文华赵景辉肖金霞肖红王晓莹张瑜
Owner SHAANXI JIAHE PHYTOCHEM
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