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Acid catalytic synthesis method and application of phenoxyacetate derivatives

A technology of phenoxy acetate and synthesis method, which is applied in the direction of chemical instruments and methods, drug combination, carboxylate preparation, etc., can solve the problems of heavy metal ions being greatly affected and not conforming to environmental protection, etc., so as to promote the occurrence of reactions, It has the effect of structural diversity and low price

Active Publication Date: 2019-11-08
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, heavy metal ions have a great impact on the environment, which is not in line with the purpose of green environmental protection and green chemistry.

Method used

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  • Acid catalytic synthesis method and application of phenoxyacetate derivatives
  • Acid catalytic synthesis method and application of phenoxyacetate derivatives
  • Acid catalytic synthesis method and application of phenoxyacetate derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] At room temperature, successively weigh ethyl phenyldiazoacetate 1a (0.5mmol) and phenol 2a (0.8mmol) into a 25mL Schlenk reaction tube, add 5mL of 1,2-dichloroethane under air atmosphere, Stir at room temperature for 2 minutes, slowly add 0.1 mmol (10 μL) of 98% trifluoromethanesulfonic acid into the micro-injector, continue the reaction at room temperature for 20 minutes, TLC detects that the raw materials have reacted completely, stop the reaction; concentrate under reduced pressure to remove volatile components, Silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) gave the target product 3a (83 mg, yield 65%) in a colorless, transparent and viscous form , the target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0041] Embodiment 2 (comparative example: different catalyst contrasts)

[0042]

[0043] At room temperature, successively weigh ethyl phenyldiazoacetate 1a (0.5mmol) and phenol 2a (0.8mmol) into a 25mL Schlenk reaction tube, add 5mL of 1,2-dichloroethane under air atmosphere, Stir at room temperature for 2 minutes, slowly add 96% sulfuric acid 0.1mmol (5.3μL) into the micro-injector, continue to react at room temperature for 20min, TLC detects that the raw materials have reacted completely, stop the reaction; concentrate under reduced pressure to remove volatile components, silica gel column chromatography Separation (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1), the target product 3a (58 mg, yield 45%) was obtained as a colorless, transparent and viscous product, the target product Confirmed by NMR and high-resolution mass spectrometry.

Embodiment 3

[0044] Embodiment 3 (comparative example: different catalyst contrasts)

[0045]

[0046] At room temperature, successively weigh ethyl phenyldiazoacetate 1a (0.5mmol) and phenol 2a (0.8mmol) into a 25mL Schlenk reaction tube, add 5mL of 1,2-dichloroethane under air atmosphere, Stir at room temperature for 2 minutes, slowly add 72% perchloric acid 0.1mmol (7.9μL) into the micro-injector, continue to react at room temperature for 20min, TLC detects that the raw materials have reacted completely, stop the reaction; concentrate under reduced pressure to remove volatile components, silica gel Column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=10:1) gave the target product 3a (78 mg, yield 55%) in a colorless, transparent and viscous form. The target product was confirmed by NMR and high-resolution mass spectrometry.

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Abstract

The invention discloses an acid catalytic synthesis method and application of phenoxyacetate derivatives. In the method, an O-H insertion reaction is performed on one diazo ester compound and one phenolic compound by an acid catalyst to form a C-O bond to generate one corresponding phenoxyacetate derivative. The method provided by the invention adopts an acid as the catalyst, has mild conditions (room temperature), is green and high-efficiency, can realize a gram-scale reaction, and has industrial application prospects; the method does not need transition metal catalysis, avoids pollution to the environment caused by metal ions in post-treatment, and conforms to the purpose of green chemistry; and in addition, the developed methodology is applied to certain natural phenolic products or phenolic medicines with significant pharmacological activity to obtain one corresponding O-H insertion product, natural product magnolol and honokiol are taken as examples, experiments find that the anti-tumor and anti-inflammatory activity of the O-H insertion products are generally higher than those of the magnolol and the honokiol respectively, the anti-tumor activity is particularly obvious, andthe derivatives have the possibility of becoming a medicine and provides more choices for sources of the novel medicine.

Description

technical field [0001] The invention relates to an acid-catalyzed synthesis method and application of phenoxy acetate derivatives. Background technique [0002] The O-H insertion reaction between diazo compounds and phenolic compounds is one of the most common methods for constructing C-O bonds. Usually this type of reaction requires the catalysis of transition metals, commonly used catalysts include: porphyrin-coordinated iron (Nature Chemistry, 2010, 2:546), porphyrin-coordinated rhodium (Organic Letters, 2008, 39:1529), palladium-catalyzed (Organic & Biomolecular Chemistry, 2013, 11:5998) and some special copper salts or copper complexes (Journal of Organometallic Chemistry, 2016, 805: 122). However, heavy metal ions have a great impact on the environment, which is not in line with the purpose of green environmental protection and green chemistry. If the use of transition metal catalysts can be avoided, a cheap, easy-to-obtain, green and high-performance method for the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/736C07C69/712A61P35/00A61P35/02A61P29/00
CPCC07C67/31C07C69/736C07C69/712A61P35/00A61P35/02A61P29/00
Inventor 黄和张志朋徐军黄菲王雪晴于杨戴传超梅艳珍乔纳森·贝尔
Owner NANJING NORMAL UNIVERSITY
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