Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Chromane compound and preparation method thereof

A compound and chromane technology, applied in the field of trifluoromethylated chromane compounds and their preparation, to achieve the effects of mild reaction conditions and simple operation

Inactive Publication Date: 2019-02-12
XINYANG NORMAL UNIVERSITY
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the reported synthetic methods of chromanes are mainly through copper-catalyzed Ullmann coupling (J.Org.Chem.2009,74,5075), reduction of chromones (PCT Int.2009,2009062285) Obtained, but for the synthesis of trifluoromethylated chromane compounds, there is no report yet

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
  • Chromane compound and preparation method thereof
  • Chromane compound and preparation method thereof
  • Chromane compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0021] Described a kind of chromane compound and preparation method thereof, comprises the following steps:

[0022] Disperse the olefin of structure (I), the trifluoromethyl reagent of structure (II) and the oxidizing agent in the solvent, heat and stir to obtain the chromane compound with structure (III):

[0023]

[0024] The specific structure of III is:

[0025]

[0026] Described oxidizing agent is potassium persulfate, sodium persulfate or ammonium persulfate;

[0027] The solvent is dimethylsulfoxide, acetonitrile, 1,2-dichloroethane, N,N-dimethylformamide, tetrahydrofuran, ethanol, acetone, 1,4-dioxane or ethyl acetate a kind of

[0028] The mol ratio of described olefin and trifluoromethyl reagent is 1:1.5-1:2;

[0029] The molar ratio of the olefin to the oxidizing agent is 1:1-1:3;

[0030] Described reaction temperature is 25 ℃-60 ℃;

[0031] The reaction time is 12-20h.

Embodiment 1

[0033] In a clean and dry 20mL Schlenk reaction tube, add 1mmol of 4-tert-butyl-enylphenol, 1.6mmol of sodium trifluoromethanesulfinate, 3mmol of potassium persulfate, and then add 4mL of dimethyl Using sulfoxide as a solvent, the reaction tube was sealed and placed in an oil bath at 50° C. for heating for 20 hours. After the reaction, ethyl acetate was added to extract the reaction mixture, and then water was added to extract the reaction solvent. The organic phase was spin-dried by a rotary evaporator, and the resulting residue was passed through a silica gel column with petroleum ether and ethyl acetate as eluents. After separation, the target product was obtained as a colorless oily liquid with a yield of 50%.

[0034] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 1a As shown, the NMR fluorine spectrum is shown as Figure 1b As shown, the carbon NMR spectrum is as Figure 1c shown. It can be confirmed fr...

Embodiment 2

[0036] In a clean and dry 20mL Schlenk reaction tube, add 1mmol of 4-cyano-enbutylphenol, 1.8mmol of sodium trifluoromethanesulfinate, 3mmol of potassium persulfate, and then add 4mL of dimethyl sulfide Sulfone was used as a solvent, and the reaction tube was sealed and placed in an oil bath at 60° C. for heating for 18 hours. After the reaction, ethyl acetate was added to extract the reaction mixture, and then water was added to extract the reaction solvent. The organic phase was spin-dried by a rotary evaporator, and the resulting residue was passed through a silica gel column with petroleum ether and ethyl acetate as eluents. After separation, the target product was obtained as a colorless oily liquid with a yield of 41%.

[0037] The proton nuclear magnetic resonance spectrum of the product prepared in this embodiment is as follows: Figure 2a As shown, the NMR fluorine spectrum is shown as Figure 2b As shown, the carbon NMR spectrum is as Figure 2c shown. It can be ...

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 discloses a chromane compound and a preparation method thereof. The preparation method comprises the following specific steps: dispersing olefin shown as a structure (I), a trifluoromethyl reagent shown as a structure (II) and an oxidizing agent in a solvent; heating and stirring the mixture to obtain the chromane compound shown as a structure (III), wherein the structure (III) is shown in the description. The invention further provides a novel method for building a trifluoromethylation chromane compound by taking an olefin compound (I) as a starting raw material of a reaction and sodium trifluoromethanesulfonate (II) as a trifluoromethyl source, and persulfate as an oxidizing agent, and performing free radical addition, free radical arylation cyclization and oxidization on trifluoromethyl and the olefin. The method has the advantages of mild reaction conditions, easiness in operation, diverse products, and the capability of realizing scale production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a trifluoromethylated chromane compound and a preparation method thereof. Background technique [0002] Chromane compounds are an important class of organic chemical raw materials, and have shown broad application prospects in many fields such as organic synthesis, polymers, synthetic drugs, and pesticides. Compounds containing trifluoromethyl groups have unique biological and chemical activities. Therefore, the trifluoromethyl-containing chromane compounds will have the properties and characteristics of both chromane and trifluoromethyl-containing compounds. So far, the reported synthetic methods of chromanes are mainly through copper-catalyzed Ullmann coupling (J.Org.Chem.2009,74,5075), reduction of chromones (PCT Int.2009,2009062285) and However, there is no report on the synthesis of trifluoromethylated chromanes. Contents of the invention [0003] In order to overcome ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58
CPCC07D311/58
Inventor 唐林杨禛焦景超杨亚凯赵薏茹崔俊艳
Owner XINYANG NORMAL UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com