Preparation method of sateripol compounds

The technology of a compound and gentisol, which is applied in the field of preparation of gentisol compounds, can solve the problems of high price, unfavorable mass production, and high raw material cost, and achieves the effects of ideal yield, reduced cost and easy implementation.

Inactive Publication Date: 2016-06-15
HARBIN INST OF TECH AT WEIHAI
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest defect of the above method is that the cost of raw materials is relatively high, especially

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of sateripol compounds

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0016] Example 1: 2-hydroxymethyl-4-methoxyphenol ( 3 , See attached picture) composition

[0017] Add 5ml deionized water and 4-methoxyphenol ( 2 , See attached picture, according to references Organic&biomolecularchemistry 12.19 (2014): 3100. Preparation, 2.0 mmol), sodium metaborate tetrahydrate (16.0 mmol), 0.75 ml of formalin solution, stirred at 40°C for 16 hours, and TLC detected the completion of the reaction. The reaction was quenched by adding 1 ml of dilute hydrochloric acid, the reaction solution was extracted with ethyl acetate (20 mLx3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain 2-hydroxymethyl-4-methoxy Base phenol, the yield was 91%.

Example Embodiment

[0018] Example 2: Gentianquinone (2-hydroxymethyl-1,4-p-benzodiquinone, 4 , See attached picture) composition

[0019] Add 2 ml of acetonitrile, 2 ml of water, 2-hydroxymethyl-4-methoxyphenol ( 3 , See the figure, 1.0mmol), cerium ammonium nitrate (2.5mmol), stir the reaction at 0°C for 2 hours, and TLC detects the end of the reaction. The reaction solution was extracted with dichloromethane (10 mL×3), the organic phases were combined, dried with anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain gentioquinone with a yield of 87%. Proton nuclear magnetic resonance spectroscopy 1 HNMR(400MHz, CDCl 3 )σ6.79(s,1H),6.72(s,2H),4.51(s,2H); carbon NMR spectrum 13 CNMR(100MHz, CDCl 3 )σ187.7, 187.5, 147.4, 136.7, 136.5, 131.1, 59.1.

Example Embodiment

[0020] Example 3: Gentianol (2-hydroxymethyl-1,4-hydroquinone, 1 , See attached picture) composition

[0021] Add 0.5 ml of methylene chloride, 1.5 ml of water, 2-hydroxymethyl-1,4-quinone ( 4 , See the attached picture, 0.2mmol), sodium dithionite (0.6mmol), stir the reaction at room temperature for 2 hours, TLC detects the end of the reaction. The reaction was quenched by adding 1 ml of dilute hydrochloric acid, shaking and liquid separation, the aqueous phase was extracted with an organic solvent (10 mLx3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain gentisol with yield Is 80%. Proton nuclear magnetic resonance spectroscopy 1 HNMR(400MHz,DMSO-d 6 )σ6.72(s,1H), 6.54(d,1H,J=8.4Hz), 6.41(d,1H,J=8.4Hz), 4.39(s,2H); carbon NMR spectrum 13 CNMR(100MHz,DMSO-d 6 )σ150.2,146.8,129.8,115.5,114.4,113.7,58.7; high resolution mass spectrometry HRMS (TOFMSES + ) m / z :CalcdforC 7 H 8 O 3 [M +...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to a preparation method of sateripol compounds, and belongs to the field of chemical synthesis. 4-alkoxy saligenol compounds are prepared by carrying out a reaction of 4-alkoxy phenol compounds and aldehyde ketone compounds, the gentian quinone compounds are prepared by carrying out an oxidation reaction of the 4-alkoxy saligenol compounds, and the sateripol compounds (shown in the attached drawing described in the specification) are prepared by carrying out a reduction reaction of the gentian quinone compounds. The preparation method has the advantages of low production cost, simple process conditions, easy control, high total yield and the like, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of gentianol compounds. Background technique [0002] Gentianol is an organic compound extracted from Streptomyces for the first time. It not only has high antioxidant activity, promotes angiogenesis, and inhibits apoptosis ( J. Microbial. Biotechnol. 2016, 16 ,475), but also showed inhibitory activity against influenza virus H1N1 and H3N2, half inhibitory concentration (IC 50 ) values ​​are 5.0 and 5.9 μmol L -1 , the selection index (SI) is 3.7 and 3.0 respectively ( Chin. Pharm. J. 2014, 49 ,632). In addition, chlorgentianol has extremely high antifouling activity, and its EC to a variety of marine fouling organisms 50 reached 0.67μg / mL ( Mar. Biotechnol .2006, 8 ,634), which is far below the antifouling agent standard stipulated by the US Navy (EC 50 ≤25μg / mL). [0003] Many people have done related work on the synthesis of gentianol. Wherein, Ahmadibeni utilizes 2,5-dimethylol benzaldehyd...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C37/07C07C39/11
CPCC07C41/30C07C37/07C07C46/06C07C43/23C07C50/28C07C39/11
Inventor 王龙飞王洪双张振国程云飞张博淞李惠静吴彦超周培林
Owner HARBIN INST OF TECH AT WEIHAI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap