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α-(biphenoxy)acetate derivative and its synthesis method

A biphenoxy, synthetic method technology, applied in the field of α-(biphenoxy) acetate derivatives and their synthesis, to achieve the effects of mild reaction conditions, easy large-scale production, and accelerated reaction

Active Publication Date: 2021-06-29
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The obtained series of derivatives are compared with magnolol or honokiol to see if some of its pharmacological effects can be enhanced or produce new pharmacological effects. These are all unknown and unpredictable, and there is no disclosure or report in the prior art. The novelty is sufficient, and it is also the value of the present invention

Method used

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  • α-(biphenoxy)acetate derivative and its synthesis method
  • α-(biphenoxy)acetate derivative and its synthesis method
  • α-(biphenoxy)acetate derivative and its synthesis method

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Effect test

preparation example Construction

[0033] Catalyst preparation: Sludge from a sewage treatment plant in Dalian, China, was dried in a muffle furnace at 105 °C to constant weight, and heated to 600°C, continuous carbonization for 4 hours, and the carbonaceous material (SW) derived from sewage sludge can be obtained after the temperature in the furnace drops to room temperature; in order to change the surface activity of SW, different acids are used to treat SW. During acid treatment, by mixing carbonized SW with the same volume of HCl (20.5 wt%), HClO 4 (35.4wt%), H 2 SO 4 (63.4wt%) and HNO 3 (40.5wt%) were impregnated for 24 hours to prepare 50 mL of different acid-treated SWs; then, wash SW-HCl and SW-HClO with deionized water, respectively 4 、SW-H 2 SO 4 and SW-HNO 3 Until the pH of the washing liquid reaches 6-7, the solid is recovered and dried at room temperature to obtain the corresponding acid-treated surface-modified sludge carbon catalyst SW-HCl, SW-HClO 4 、SW-H 2 SO 4 and SW-HNO 3 . Note: T...

Embodiment 1

[0038]

[0039] At room temperature, successively weigh methyl p-chlorophenyldiazoacetate 1a (0.5mmol), magnolol 2a (0.70mmol), SW-HClO 4 (50mg) into a dry and clean 25mL Schlenk reaction tube, under air atmosphere, add 5mL of 1,2-dichloroethane, stir at room temperature for 2-5 minutes, and transfer to an oil bath magnetic stirring heater at 70°C Reacted for 24 hours, TLC detected that the raw material had reacted completely, stopped the reaction, the reaction solution was cooled to room temperature, suction filtered, the filter cake was washed with dichloromethane until the filtrate was colorless, concentrated under reduced pressure to remove volatile components, and separated by silica gel column chromatography ( Eluent: petroleum ether (60-90° C.) / ethyl acetate, v / v=5:1), the target product 3a (168 mg, yield 75%) was obtained as a white solid, and the target product was tested by NMR and high Confirmation by resolution mass spectrometry.

Embodiment 2

[0040] Embodiment 2 (comparative example: different catalyst contrasts)

[0041]

[0042] At room temperature, successively weigh methyl-p-chlorophenyldiazoacetate 1a (0.5mmol), magnolol 2a (0.70mmol), SW-HCl (50mg) in a dry and clean 25mL Schlenk reaction tube, in air Under the atmosphere, add 5mL of 1,2-dichloroethane, stir at room temperature for 2-5 minutes, and transfer to an oil bath magnetic stirring heater at 70°C to react for 24 hours. TLC detects that the raw materials have reacted completely, stop the reaction, and The reaction solution was cooled to room temperature, filtered with suction, the filter cake was washed with dichloromethane until the filtrate was colorless, concentrated under reduced pressure to remove volatile components, separated by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate ester, v / v=5:1), the target product 3a (96 mg, yield 43%) was obtained as a white solid, and the target product was confirmed by NMR an...

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Abstract

The invention discloses α-(biphenoxy) acetate derivatives and a preparation method thereof. Using α-diazo ester honokiol or honokiol (honokiol and honokiol are isomers each other) as the starting material, the improved sludge charcoal treated with perchloric acid as the catalyst, in Under heating conditions, in the air atmosphere, the O-H insertion of the magnolol compound is completed through the formation of metal carbene, the construction of the C-O bond is realized, and the α-(biphenoxy) acetate derivative is generated in one step reaction. The catalyst used in this method is prepared from the remaining sludge after urban sewage treatment. The reaction raw materials are easy to obtain, the conditions are mild, and the yield is good, and the reaction on a gram scale can be realized. The pharmacological effects of magnolol compounds and the current In the clinical use, the possible pharmacological effects of the series of α-(biphenoxy) acetate derivatives prepared under this method are listed. At present, the pharmacological activity of this series of compounds is still being tested. The present invention will not elaborate too much.

Description

technical field [0001] The invention relates to the preparation and method of a series of novel compound α-(biphenyloxy) acetate derivatives, and the application of a surface-modified sludge charcoal catalyst in the O-H insertion reaction of magnolol compounds and the construction of C-O bonds. Especially the preparation and application of a series of new compounds that may have antibacterial, anti-inflammatory, anti-tumor, hypoglycemic and lipid-lowering effects. Background technique [0002] Medicines developed with medicinal plants as the main body have played a huge role in human disease prevention and treatment, rehabilitation and health care, and reproduction in history. There are many sources of natural medicines, most of which come from plants; it is estimated that there are about 400,000 to 500,000 species of plants in the world, but only a very small number of them have been tested and studied on chemical components and their activities. my country is also one of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/31C07C69/736C07C69/712B01J27/10B01J27/06B01J27/053B01J27/25B01J35/10A61P31/04
CPCA61P31/04C07C67/31C07C69/712C07C69/736B01J27/053B01J27/06B01J27/10B01J27/25B01J35/60
Inventor 黄和张志朋黄菲于杨易享炎乔纳森贝尔
Owner NANJING TECH UNIV
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