Method for synthesizing 3,4-di-oxygen-[3-benzene alkene propionyl]quinic acid compounds

A technology of phenylacryloyl and phenylallylic acid, which is applied in 3 fields of synthesis, can solve problems such as low yield, and achieve the effects of high yield, simple post-processing, and simple operation

Inactive Publication Date: 2008-10-29
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are not many reports on the synthesis methods of dicaffeoylquinic acid compounds. Generally, the acid chloride method is commonly used to prep

Method used

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  • Method for synthesizing 3,4-di-oxygen-[3-benzene alkene propionyl]quinic acid compounds
  • Method for synthesizing 3,4-di-oxygen-[3-benzene alkene propionyl]quinic acid compounds
  • Method for synthesizing 3,4-di-oxygen-[3-benzene alkene propionyl]quinic acid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 :Synthesis of Compound (1) under Catalytic Condensation of Dicyclohexylcarbodiimide

[0030] Add 2.5 millimoles of 3,4-diacetoxy phenylacrylic acid, 3 millimoles of dicyclohexylcarbodiimide, and 20 ml of anhydrous dichloromethane to the reaction flask, and stir at room temperature for 20 minutes. After white turbidity appears, Add 1 mmol of quinic acid lactone and 0.3 mmol of 4-dimethylaminopyridine (DMAP). The whole solution is reacted at room temperature for 12 hours. The insoluble matter is removed by suction filtration, the solvent is evaporated, and the solvent is removed to obtain a white solid, which is then added 15 ml of tetrahydrofuran, then 5 ml of 1N hydrochloric acid was added dropwise, and the reaction was carried out at room temperature for 48 hours. The ratio of product to raw material was detected by thin layer chromatography (TLC) and the ratio of the product and the raw material did not change. The reaction system was saturated with salt and e...

Embodiment 2

[0032] Example 2 :Synthesis of compound (1) under catalytic condensation of methyl isobutyl carbodiimide

[0033] Add 2.5 millimoles of p-3,4-diacetoxy benzene acrylic acid, 3 millimoles of methyl isobutyl carbodiimide, and 20 ml of anhydrous dichloromethane to the reaction flask. Stir at room temperature for 20 minutes, and a white color appears. After turbidity, add 1 mmol of quinic acid lactone, 0.3 mmol of 4-dimethylaminopyridine (DMAP), the whole solution was reacted at room temperature for 12 hours, suction filtered to remove insoluble matter, and then 5 ml of 1N hydrochloric acid was added dropwise. React at room temperature for 48 hours. The ratio of product to raw material is no longer changed by TLC. The reaction system is saturated with salt and extracted with chloroform (20 ml×4). The combined chloroform layer is washed with plenty of water, and washed with saturated brine. Dry with sodium sulfate. Use reversed-phase silica gel column RP-C 18 Column chromatography se...

Embodiment 3

[0035] Example 3 :Synthesis of compound (1) under the condition that 4-pyrrolidinylpyridine is an organic base

[0036]Add 2.5 millimoles of 3,4-diacetoxy phenylacrylic acid, 3 millimoles of dicyclohexylcarbodiimide, and 20 ml of anhydrous dichloromethane to the reaction flask, and stir at room temperature for 20 minutes. After white turbidity appears, Add 1 mmol of quinic acid lactone and 0.3 mmol of 4-pyrrolidinylpyridine (PPY). The whole solution is reacted at room temperature for 12 hours. The insoluble matter is removed by suction and filtration. Then 5 ml of 1N hydrochloric acid is added dropwise, and the reaction is at room temperature. After 48 hours, it was detected by TLC that the ratio of the product to the raw material did not change. The reaction system was saturated with salt, extracted with chloroform (20 ml×4), the combined chloroform layer was washed with plenty of water, washed with saturated brine, and dried with anhydrous sodium sulfate. . Use reversed-phase ...

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Abstract

The invention relates a method for synthesizing 3,4-di-o-[3-phenyl propionyl] quinic acid compounds, which comprises allowing substituted beta-phenylacrylic acid compounds (II) and quinic acid lactones (III) to condensate in the presence of dicyclohexylcarbodiimide (DCC) and analog thereof as condensing agent and organic alkali as catalyst to obtain compounds (IV), and hydrolyzing to obtain compounds (I). The condensation reaction is carried out in organic solvent, and hydrolysis is carried out in diluted acid solution or alkali condition such as sodium methoxide and sodium ethoxide. The method has mild reaction condition, simple operation, short step, simple post treatment, and middle to good yield.

Description

Technical field [0001] The present invention relates to the field of organic chemistry, in particular to a method for synthesizing 3,4-di-oxy-[3-phenylenepropionyl]quinic acid compounds. Background technique [0002] 3,4-Di-oxy-[3-phenylalyl]quinic acid compounds are a general term for a class of common natural products with multiple physiological activities, among which the most famous is dicaffeoylquinic acid compounds (Dicaffeoyl quinic acid, DCQ). This type of natural product is commonly found in Chinese herbal medicines for protecting liver and choleretics. Among them, cynarin (1,3-di-oxy-caffeoylquinic acid) has been studied most widely. Most of these compounds have hepatoprotective and choleretic effects, and have protective effects on liver damage caused by macrophages and carbon tetrachloride. 1,5-Di-oxy-caffeoyl quinic acid (Dicaffeoyl quinic acid IBE5) is the active ingredient of the traditional Chinese medicine Inula, and its pharmacological activity has been studied ...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C69/732C07C67/00
Inventor 李校堃胡利红黄可新叶发青董建勇赵昱巫秀美瞿佳
Owner WENZHOU MEDICAL UNIV
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