(E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound and preparation method thereof

A technology of hydroxystyrene and phenyl chloroacetate, which is applied in the preparation of carboxylic acid halides, digestive systems, organic chemistry, etc., can solve the problems of easy oxidation and instability, and achieve stable structure, convenient operation, and mild reaction conditions Effect

Inactive Publication Date: 2013-04-03
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

from figure 1 It can be seen that the resveratrol molecule contains 3 phenol-OH, so it is very unstable and easily oxidized

Method used

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  • (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound and preparation method thereof
  • (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound and preparation method thereof
  • (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound and preparation method thereof

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Experimental program
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Embodiment 1

[0031] A preparation method of (E)-3-hydroxyl-5-(hydroxystyryl)-2-chlorophenylacetate compound, specifically comprising the following steps:

[0032] (1) Add 114mg (2.2mmol) resveratrol into a 100mL three-necked flask, and stir with 20mL dichloromethane for 5-15min to obtain a white turbid liquid;

[0033] Add 1 mL of triethylamine to the white turbid solution obtained above in an ice bath, and stir for 2 to 5 minutes to obtain a yellow clear solution;

[0034] Slowly add 248 mg (2.2 mmol) of chloroacetyl chloride dropwise to the yellow clear liquid obtained above under ice bath conditions, remove the ice bath after the dropwise addition, and raise the temperature to 25°C for esterification for 2 to 5 hours to obtain a reaction liquid;

[0035] (2), control the temperature of the water bath obtained in step (1) to 20-40°C, and the pressure to 0.07-0.1MPa to carry out the first decompression concentration to remove excess dichloromethane and triethylamine in the react...

Embodiment 2

[0039] A preparation method of resveratrol derivatives, specifically comprising the following steps:

[0040] (1) Add 114mg (2.2mmol) resveratrol into a 100mL three-neck flask, stir 20mL tetrahydrofuran for 5-15min to obtain a white clear liquid;

[0041] Add 1 mL of triethylamine to the white clear liquid obtained above in an ice bath, and stir for 2 to 5 minutes to obtain a white turbid liquid;

[0042] Slowly add 248 mg (2.2 mmol) of chloroacetyl chloride dropwise to the white cloudy liquid obtained above under ice bath conditions, remove the ice bath after the dropwise addition, and raise the temperature to 25°C for esterification reaction for 2 to 5 hours to obtain a reaction liquid;

[0043](2) Control the temperature of the water bath obtained in step (1) between 20-40°C and the pressure at 0.07-0.1 MPa to conduct the first vacuum concentration to remove tetrahydrofuran and triethylamine in the reaction liquid, then concentrate The final crude produ...

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Abstract

The invention discloses a (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound and a preparation method thereof. By using dichloromethane or tetrahydrofuran as a solvent and triethylamine as an acid binding agent, chloracetyl chloride and resveratrol used as reactants are subjected to esterification reaction at 0-28 DEG C for 2-5 hours to obtain the white solid (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound. The (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound has stable structure, and can not be easily oxidized; the preparation method has the characteristic of simple preparation process and is convenient to operate; and meanwhile, the obtained (E)-3-hydroxy-5-(hydroxystyryl)-2-phenyl chloroacetate compound has similar structural features to resveratrol, and reserves the group having drug effect in the resveratrol.

Description

technical field [0001] The invention relates to a (E)-3-hydroxy-5-(hydroxystyryl)-2-chloroacetic acid phenyl ester compound and a preparation method thereof. Background technique [0002] Resveratrol is a non-flavonoid polyphenolic compound containing a stilbene structure and has various pharmacological activities such as anti-atherosclerosis, anti-coagulation, anti-lipid oxidation, anti-bacterial and anti-inflammatory, immune regulation, neuroprotection, and liver protection. The schematic diagram of the chemical structure of resveratrol is shown in figure 1 shown. from figure 1 It can be seen that the resveratrol molecule contains 3 phenol-OH, so it is very unstable and easily oxidized. [0003] Studies have shown that the position and number of hydroxyl groups on the stilbene benzene ring are closely related to the antioxidant activity of resveratrol derivatives. The present invention uses it as a lead compound to mainly modify the structure of hydroxyl groups in its s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/63C07C67/14A61P9/10A61P7/02A61P39/06A61P31/00A61P29/00A61P37/02A61P25/00A61P1/16
Inventor 任玉杰杜成
Owner SHANGHAI INST OF TECH
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