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Synthesis method of Formononetin

A technology for formononetin and a synthesis method, which is applied in directions such as organic chemistry, can solve the problems of severe reaction conditions, complex reaction products, expensive reagents and the like, and achieves the effects of high reaction efficiency, high application value, and easy availability of raw materials

Inactive Publication Date: 2011-05-25
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The cyclization step is the process of synthesizing isoflavones from deoxybenzoin. Due to the long reaction time, the reaction conditions are severe; the reagents used are expensive; the yield is low; the reaction products are complex and require complicated purification to obtain the final product. little value

Method used

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  • Synthesis method of Formononetin

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Effect test

example 1

[0014] A synthetic method of formononetin, comprising the following steps:

[0015] The first step, condensation, in the drying reactor, add resorcinol, p-methoxyphenylacetic acid, boron trifluoride ether, the quality of resorcinol, p-methoxyphenylacetic acid, boron trifluoride ether The ratio is 1:1.5:2, at 80-90 ℃, the degree of vacuum is -0.08MPa, and the reaction is heated for 30min. After the reaction is completed, add water, the quality of the water is 1 times the total mass of the feed, and heat and reflux at 100-110 ℃ for 20min , the conventionally processed intermediates,

[0016] The second step, cyclization, in the dry reaction tank, add the intermediate, triethyl orthoformate, morpholine, DMF and glacial acetic acid, the mass ratio of the intermediate, triethyl orthoformate, morpholine, DMF and glacial acetic acid 1: 0.2: 0.2: 5: 0.3, separate by-product ethanol, heat under reflux for 6h, control the temperature to 110-135 ° C, after the reaction is completed, rec...

example 2

[0019] The first step, condensation, in the drying reactor, add resorcinol, p-methoxyphenylacetic acid, boron trifluoride ether, the quality of resorcinol, p-methoxyphenylacetic acid, boron trifluoride ether The ratio is 1:1.5:6, at 80-90 ℃, the vacuum degree is -0.08MPa, heating the reaction for 60min, after the reaction is completed, add water, the quality of the water is 3 times the total mass of the feeding , the conventionally processed intermediates,

[0020] The second step, cyclization, in the dry reaction tank, add the intermediate, triethyl orthoformate, morpholine, DMF and glacial acetic acid, the mass ratio of the intermediate, triethyl orthoformate, morpholine, DMF and glacial acetic acid 1: 0.2: 0.2: 10: 0.3, separate by-product ethanol, heat under reflux for 8h, control the temperature to 110-135 ° C, after the reaction is completed, recover DMF under reduced pressure, cool to 20 ° C, and add 5% of the mass of the intermediate to the residue. times the saturate...

example 3

[0023] A synthetic method of formononetin, comprising the following steps:

[0024] The first step, condensation, in the drying reactor, add resorcinol, p-methoxyphenylacetic acid, boron trifluoride ether, the quality of resorcinol, p-methoxyphenylacetic acid, boron trifluoride ether The ratio is 1:1.5:10, at 80-90 ℃, the degree of vacuum is -0.08MPa, heating and reacting for 90min, after the reaction is completed, add water, the quality of the water is 5 times the total mass of the feed, heat and reflux at 100-110 ℃ for 20min , cooled to precipitate crystallization, and the intermediate was obtained by conventional treatment,

[0025] The second step, cyclization, in the dry reaction tank, add the intermediate, triethyl orthoformate, morpholine, DMF and glacial acetic acid, the mass ratio of the intermediate, triethyl orthoformate, morpholine, DMF and glacial acetic acid 1: 0.5: 0.3: 8: 0.6, separate the reaction by-product ethanol, heat to reflux for 10h, control the temper...

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Abstract

The invention relates to a synthesis method of formononetin, and the method comprises the following steps: condensation: in a dry reactor, adding resorcin, p-metoxybenzene acetate, boron trifluoride and ethyl ether, heating for reaction, adding water after the reaction finishes, heating under reflux, cooling to precipitate crystals, filtering, washing with water until the solution is neutral, and drying to obtain an intermediate; and cyclization: in a dry reaction tank, adding the intermediate, triethyl orthoformate, morpholine, DMF (dimethyl formamide) and glacial acetic acid, separating out the reaction byproduct ethanol, heating under reflux, recycling the DMF reagent under reduced pressure after the reaction finishes, cooling, adding saturated sodium bicarbonate solution into the remainder, refluxing, cooling to precipitate crystals, carrying out conventional treatment to obtain crude formononetin, and refining the crude formononetin by using methanol to obtain the fine formononetin. The method can be used for solving the problem of formononetin resource shortage at present, has the advantages of accessible raw materials, efficient reaction, convenience and high application value.

Description

technical field [0001] The invention belongs to the field of fine chemical drug synthesis, in particular to a method for synthesizing formononetin. technical background [0002] Formononetin is an isoflavone compound, which has anti-cancer effect and can prevent and treat breast cancer, prostate cancer and colon cancer. Formononetin is also known as 7-hydroxy-4'-methoxyisoflavone, Formonone Flavin exists in nature in the inflorescence and flowered branches and leaves of leguminous plant olium Pratense L, and the whole plant of Ononis spinosa. The preparation of isoflavones mainly includes extraction and chemical synthesis. Compared with the extraction method, the chemical synthesis method has many advantages such as low production cost, simple process, high yield and high purity. [0003] The cyclization step is the process of synthesizing isoflavones from deoxybenzoin. This kind of method has a long reaction time and severe reaction conditions; the reagents used are expens...

Claims

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Application Information

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IPC IPC(8): C07D311/36
Inventor 郭文华肖金霞肖红王晓莹
Owner SHAANXI JIAHE PHYTOCHEM
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