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Organic synthesis method of scutellarein

A technology of organic synthesis and scutellarein, applied in the field of organic synthesis of scutellarein, to achieve the effects of high yield, mild reaction conditions and shortened reaction cycle

Inactive Publication Date: 2020-06-30
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to solve the problem that it is difficult to obtain high-purity scutellarein in large quantities through biosynthetic pathways and extraction and separation of medicinal plants in the prior art, and provides a method for organic synthesis of scutellarein

Method used

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  • Organic synthesis method of scutellarein
  • Organic synthesis method of scutellarein
  • Organic synthesis method of scutellarein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] A kind of synthetic method of scutellarein, comprises the following steps:

[0053] Step 1) the synthesis of p-methoxycinnamoyl chloride

[0054] After dissolving 1.0g of p-methoxycinnamic acid in 20ml of dichloromethane, slowly add 3ml of oxalyl chloride dropwise, then add 2 drops of dimethylacetamide (DMAC), and react at room temperature for 30min. The temperature of the reaction mixture was lowered to low temperature, and dichloromethane and unreacted oxalyl chloride were distilled off under reduced pressure to finally obtain 1.0 g of orange-yellow crystal p-methoxycinnamoyl chloride with a yield of 91%.

[0055] Step 2) Synthesis of 9-hydroxy-5,6,7,4'-tetramethoxychalcone

[0056] Add 0.8 g of 3,4,5-trimethoxyphenol to the 1.0 g p-methoxycinnamoyl chloride obtained in step 1), then slowly drop 5 ml of 48% boron trifluoride-diethyl ether (BF 3 -Et 2 O) complex compound, heated in an oil bath at 75°C for 25 minutes, and cooled to room temperature to precipitate. E...

Embodiment 2

[0062] A kind of synthetic method of scutellarein, comprises the following steps:

[0063] Step 1) the synthesis of p-methoxycinnamoyl chloride

[0064] After dissolving 1.00g of p-methoxycinnamic acid in 20ml of dichloromethane, slowly add 3ml of oxalyl chloride dropwise, then add 2 drops of DMF, and react at room temperature for 20min. The temperature of the reaction mixture was lowered to a low temperature, and dichloromethane and unreacted oxalyl chloride were distilled off under reduced pressure to finally obtain 0.9 g of orange-yellow crystal p-methoxycinnamoyl chloride with a yield of 82%.

[0065] Step 2) Synthesis of 9-hydroxy-5,6,7,4'-tetramethoxychalcone

[0066] Add 0.8 g of 3,4,5-trimethoxyphenol to the 0.9 g of p-methoxycinnamoyl chloride obtained in step 1), then slowly drop 5 ml of 40% aluminum chloride solution, and heat in an oil bath at 65°C After cooling to room temperature for 40 minutes, a precipitate precipitated out. Excessive water was added, and a ...

Embodiment 3

[0072] A kind of synthetic method of scutellarein, comprises the following steps:

[0073] Step 1) the synthesis of p-methoxycinnamoyl chloride

[0074] After dissolving 1.00g of p-methoxycinnamic acid in 20ml of dichloromethane, slowly add 2ml of carbon tetrachloride dropwise, then add 2 drops of pyridine, and react at room temperature for 30min. The temperature of the reaction mixture was lowered to low temperature, and dichloromethane and unreacted carbon tetrachloride were distilled off under reduced pressure to finally obtain 0.72 g of orange-yellow crystal p-methoxycinnamoyl chloride with a yield of 65%.

[0075] Step 2) Synthesis of 9-hydroxy-5,6,7,4'-tetramethoxychalcone

[0076] Add 0.6 g of 3,4,5-trimethoxyphenol to the 0.72 g of p-methoxycinnamoyl chloride obtained in step 1), then slowly drop 5 ml of 40% ferric chloride solution, and heat in an oil bath at 75°C for 30 min , cooling to room temperature precipitated out. Excessive water was added, and a large amou...

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Abstract

The invention provides an organic synthesis method of scutellarein, wherein the organic synthesis method comprises the following steps: 1) by using p-methoxycinnamic acid as a raw material, synthesizing p-methoxycinnamoyl chloride under the catalytic action of an acyl chloride reagent and a catalyst; step 2) carrying out esterification reaction on p-methoxycinnamoyl chloride and 3,4,5-trimethoxyphenol under the action of Lewis acid, and then carrying out Fries rearrangement, so as to obtain 9-hydroxy-5,6,7,4'-tetramethoxychalcone; step 3) performing intramolecular cyclization on the 9-hydroxy-5,6,7,4'-tetramethoxychalcone under the action of an oxidizing agent to obtain 5,6,7,4'-tetramethoxyflavone; and step 4) demethylating the 5,6,7,4'-tetramethoxyflavone under the protection of N2 underthe action of a demethylating reagent to generate scutellarin. As the reaction operation is simple and safe, the post-treatment operation is easy, and the yield is high, the method has a wide industrial application prospect.

Description

technical field [0001] The invention relates to the total synthesis of active ingredients of natural medicines, in particular to an organic synthesis method of scutellarein. Background technique [0002] Flavonoids mainly come from plants in nature and are even found in fruits and vegetables. Due to the presence of aromatic groups and oxygen-containing groups, flavonoids have various activities such as anti-oxidation, anti-coagulation, anti-inflammation, pain relief, anti-tumor, liver protection, anti-virus, lowering blood pressure, and promoting wound healing. This class of compounds has attracted increasing attention due to their low toxicity and thus their potential as pharmaceutical or food preservatives. In addition, flavonoids have been shown to have anticancer activity, and flavonoid-based anticancer therapies are under development. The flavonoid compound scutellarein (Scutellarein, chemically named 5,6,7,4'-tetrahydroxyflavone) is obtained from the traditional Chin...

Claims

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Application Information

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IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 殷志琦周长威娄云云
Owner CHINA PHARM UNIV