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The preparation method of 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester

A technology of phenyl hydroxy and diol esters, which is applied in the field of compound synthesis, can solve the problems of high preparation cost, complicated process, and low yield, and achieve the effects of low raw material cost, simple process, and high yield

Active Publication Date: 2021-01-29
GUANGDONG HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its active ingredients have various physiological activities, such as anti-hepatotoxicity, anti-tumor, anti-inflammatory, bile excretion, insecticide, anti-oxidation, etc.; natural linear diphenylheptane compounds, typical structure, diverse and significant physiological activities, in recent years Becoming the focus of attention, 1,7-bis(4-phenylhydroxy)heptyl-3,5-diol ester is also known as 3,5-diacetoxy-1,7-bis(4-hydroxyphenyl) Heptane, which has been proved to have the biological activity of inhibiting the proliferation of human T-cell lymphoma cell line HH cells, can be applied to the preparation of medicine or food for the prevention and treatment of psoriasis; prior art for 1,7-two (4-phenylhydroxy ) Heptyl-3, the preparation of 5-diol ester mostly is to obtain through a series of procedures such as purification, chemical chromatography from Zingiberaceae Curcuma rhizome, yet this method prepares 1,7-two (4-phenylhydroxyl) heptane Base-3, the productive rate of 5-diol ester is low, procedure is complicated, and uses various chemical chromatography, and preparation cost is high, is unfavorable for present industry for 1,7-bis(4-phenylhydroxyl) heptyl-3, Large-scale production of 5-diol esters

Method used

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  • The preparation method of 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester
  • The preparation method of 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester
  • The preparation method of 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester

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Embodiment 1

[0036] 1, the preparation of 7-bis (4-phenylhydroxyl) heptyl-3,5-diol ester comprises the following steps:

[0037] (1) Using 2,4-pentanedione as a raw material, react to obtain product 2 (i.e. bisdemethoxycurcumin)

[0038] 8.0 g of 2,4-pentanedione was dissolved in 250 mL of anhydrous ethyl acetate, 2.78 g of diboron trioxide was added under stirring, and the reaction was carried out at room temperature for 30 min to obtain compound 1-1 (such as figure 1 Shown), without separation and purification directly proceed to the next step of addition reaction.

[0039] Add 36.8g of tributyl borate and 19.5g of p-hydroxybenzaldehyde to the reaction system, react for 40min, slowly add 2.9g of n-butylamine dropwise, after dropping, stir for 4h, and let stand for 12h. Add 150 mL of dilute hydrochloric acid dropwise to the reaction solution, stir for 1 hour, transfer to a separatory funnel, let stand to separate layers, discard the water layer, wash the ethyl acetate layer with water, c...

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Abstract

The invention discloses a preparation method of 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester, which comprises the following steps: (1) taking bisdemethoxycurcumin as raw material, first carrying out- The reduction reaction of C=C-gets the product 3; (2) then carries out the reduction reaction of the carbonyl under the premise of protecting the hydroxyl group on the benzene ring to get the product 5; (3) the product 5 is subjected to an esterification reaction to get the product 6, and the product 6 is then carried out The deprotection group reaction is to obtain the final product 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester. 1,7-bis(4-phenylhydroxyl)heptyl-3,5-diol ester can be obtained by chemical reaction and deprotection reaction, the reaction procedure is simple, the operation is simple, the cost of raw materials used is low, and the yield is high , suitable for large-scale industrial production of 1,7-bis(4-phenylhydroxy)heptyl-3,5-diol ester.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, more specifically, to a preparation method of 1,7-di(4-phenylhydroxy)heptyl-3,5-diol ester. Background technique [0002] Diphenylheptane compounds are a general term for a class of natural compounds with a 1,7-diphenylheptane core, which can be divided into linear and cyclic compounds according to their structures, and are mainly found in Zingiberaceae plants Compounds with special structures. Its active ingredients have various physiological activities, such as anti-hepatotoxicity, anti-tumor, anti-inflammatory, bile excretion, insecticide, anti-oxidation, etc.; natural linear diphenylheptane compounds, typical structure, diverse and significant physiological activities, in recent years Becoming the focus of attention, 1,7-bis(4-phenylhydroxy)heptyl-3,5-diol ester is also known as 3,5-diacetoxy-1,7-bis(4-hydroxyphenyl) Heptane, which has been proved to have the biological activity ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/21C07C67/29C07F7/18C07C45/62C07C49/245C07C45/64C07C49/248
CPCC07C45/62C07C45/64C07C67/29C07F7/188C07C49/248C07C49/245C07C69/21Y02P20/55
Inventor 刘博卢传坚周文陈海明韩晓东黄闰月刘敬功徐方方吴云山张玉琴
Owner GUANGDONG HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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