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Method for synthesizing 1, 7-2-(4-hydroxy phenyl)-heptane-1, 4-diene-3-ketone

A technology of hydroxyphenyl and synthetic method, which is applied in the direction of chemical instruments and methods, preparation of organic compounds, drug combination, etc., can solve the problems of high price, low purity, and low content, and achieve simple method, high purity, and easy operation Effect

Inactive Publication Date: 2018-02-23
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, 1,7-bis-(4-hydroxyphenyl)-heptane-1,4-dien-3-one only exists naturally, and can only be obtained through the extraction, separation and purification of mistletoe. Low, less content, difficult to purify, expensive and other disadvantages, therefore, research and development of a simple method for the synthesis of 1,7-bis-(4-hydroxyphenyl)-heptane-1,4-dien-3-one , so that it can be chemically synthesized and even mass-produced is very important

Method used

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  • Method for synthesizing 1, 7-2-(4-hydroxy phenyl)-heptane-1, 4-diene-3-ketone

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Embodiment 1

[0045] 1. Preparation of 3-(4-hydroxyphenyl) methyl propionate

[0046] 3-(4-Hydroxyphenyl)propanoic acid (8g, 48.14mmol) was dissolved in methanol (40mL), and concentrated sulfuric acid (0.4mL) was added dropwise to catalyze the reaction at 35°C for 4h, and part of the methanol was removed by concentration under reduced pressure. Add 10 mL of water, adjust the pH to 6 with saturated sodium bicarbonate, extract three times with 20 mL of ethyl acetate, wash three times with 20 mL of saturated brine, dry over anhydrous sodium sulfate, and remove ethyl acetate under reduced pressure to obtain 3-(4- hydroxyphenyl) propionate methyl ester.

[0047] 2. Preparation of methyl 3-(4-(methoxymethyl)phenyl)propionate methyl ester

[0048]Methyl 3-(4-hydroxyphenyl)propionate (3 g, 16.66 mmol) and N,N-diisopropylethylamine (3.5 mL, 21.65 mmol) were dissolved in anhydrous dichloromethane (50 mL) with stirring , stirred for 30min, added acetone 50mL, added dropwise bromomethyl methyl ether ...

Embodiment 2

[0061] 1. Prepare 3-(4-hydroxyphenyl) ethyl propionate

[0062] 3-(4-Hydroxyphenyl)propanoic acid (8g, 48.14mmol) was dissolved in ethanol (40mL), concentrated sulfuric acid (0.4mL) was added dropwise to catalyze the reaction at 35°C for 4h, and part of the methanol was removed by concentration under reduced pressure. Add 10 mL of water, adjust the pH to 6 with saturated sodium bicarbonate, extract three times with 20 mL of ethyl acetate, wash three times with 20 mL of saturated brine, dry over anhydrous sodium sulfate, and remove ethyl acetate under reduced pressure to obtain 3-(4- hydroxyphenyl) ethyl propionate.

[0063] 2. Preparation of ethyl methyl 3-(4-(methoxymethyl)phenyl)propionate

[0064] Ethyl 3-(4-hydroxyphenyl)propionate (3 g, 16.66 mmol) and N,N-diisopropylethylamine (3.5 mL, 21.65 mmol) were dissolved in anhydrous dichloromethane (50 mL) with stirring , stirred for 30min, added acetone 50mL, added dropwise bromomethyl methyl ether (1.7mL, 21.65mmol), heated ...

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Abstract

The invention relates to the field of pharmaceutical synthesis, in particular to a method for synthesizing 1,7-2-(4-hydroxy phenyl)-heptane-1,4-diene-3-ketone. The method, selecting 3-(4- hydroxy phenyl)propionic acid and 4-hydroxybenzaldehyde as raw materials, includes (1), subjecting the 3-(4-hydroxy phenyl)propionic acid to esterification, methyl protection, reduction and oxidation to obtain 3-(4-(methoxy methyl)phenyl)propionaldehyde; (2), subjecting the 4-hydroxybenzaldehyde to etherification and aldol reaction to obtain 4-(4-((methoxy methyl)phenyl)butyl-3-alkene-2-ketone; (3), subjecting the 4-(4-((methoxy methyl)phenyl) butyl-3-alkene-2-ketone and the 3-(4-(methoxy methyl)phenyl)propionaldehyde to aldol condensation, and allowing the reactor to react with hydrochloric acid to obtain 1, 7-2-(4-hydroxy phenyl)-heptane-1,4-diene-3-ketone. The method has the advantages of simplicity, easiness in operation, high yield and high purity.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a method for synthesizing 1,7-bis-(4-hydroxyphenyl)-heptane-1,4-dien-3-one. Background technique [0002] Tumor is one of the main diseases that endanger human health, ranking second in the death rate of various diseases. In recent years, the continuous deterioration of the environment has led to an increase in the incidence of tumors, and it is imminent to find a safe and efficient drug for tumor prevention and treatment. Pharmacological studies have confirmed that curcumin compounds have a wide range of biological activities, and have significant preventive and therapeutic effects on various physiological diseases such as cancer, neurological diseases, cardiovascular diseases, metabolic diseases, and inflammation. Among them, anti-cancer activity has attracted much attention. Curcumin can inhibit the growth of various tumor cells, has a wide anti-cancer spectrum, and has low toxi...

Claims

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Application Information

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IPC IPC(8): C07C45/65C07C49/248A61P35/00A61P15/00
CPCC07C41/48C07C45/29C07C45/64C07C45/65C07C45/74C07C67/08C07C67/31C07C69/732C07C69/734C07C43/315C07C47/277C07C47/575C07C49/255C07C49/248
Inventor 赵云丽于治国孟琳
Owner SHENYANG PHARMA UNIVERSITY
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