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

Preparation method of fluoride chalcone

A technology of fluorinated chalcones and fluorinated chalcones, which is applied in the field of preparation of fluorinated chalcones, can solve the problems of high toxicity of fluorinated reagents, difficulty in controlling the degree of reaction, complex synthesis process, etc., and achieves low price and saving The effect of economic cost and mild reaction conditions

Inactive Publication Date: 2017-05-24
NANJING UNIV OF SCI & TECH
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems in the existing preparation methods of fluorinated chalcones that the fluorinated reagents are highly toxic, the degree of reaction is difficult to control, and the synthesis process is complex, the present invention provides a catalyst-free, simple process, cheap and easy-to-obtain fluorine source, and a highly reactive Preparation method of fluorinated chalcone with mild conditions

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 fluoride chalcone
  • Preparation method of fluoride chalcone
  • Preparation method of fluoride chalcone

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0016] A kind of preparation method of fluorinated chalcone of the present invention, its reaction formula is as follows:

[0017]

[0018] First, mix acetonitrile and methanol at a volume ratio of 8:1-10:1 to make a reaction solvent, then add chalcone and electrophilic fluorinating reagent Selectfluor, stir and heat up to 65-75°C for reaction, after the reaction Cool to room temperature, evaporate to dryness to remove the reaction solvent, and then separate the product by column chromatography (V (ethyl acetate): V (petroleum ether) is 20:1), and dry to obtain fluorinated chalcone.

Embodiment 1

[0020] Step 1: Mix 450mL of acetonitrile and 50mL of methanol to make a reaction solvent.

[0021] Step 2: Add 20.8g chalcone and 70g Selectfluor into the reactor, raise the temperature to 65°C, heat and stir for 8h.

[0022] Step 3: Cool the reaction mixture to room temperature, spin dry, separate by column chromatography and evaporate to dryness to obtain 13.6 g of fluorinated chalcone.

[0023] The molecular formula of the resulting product fluorinated chalcones is:

[0024]

[0025] figure 1 , 2 and 3 are the NMR spectra of the prepared fluorinated chalcones, wherein, figure 1 for 1 H Spectrum, figure 2 for 19 F spectrum, Figure 3 is 13 C spectrum. figure 1 Through the integration and displacement position, it can be seen that the product has 10 hydrogen atoms; figure 2 It can be seen that the product contains a fluorine atom, and by observing the displacement, it can be seen that the fluorine atom is located at the α position; Figure 3 shows that the number o...

Embodiment 2

[0027] Step 1: Mix 400mL acetonitrile and 50mL methanol to make a reaction solvent.

[0028] Step 2: Add 24.2g of 4'-chlorochalcone and 63.7g of Selectfluor into the reactor, raise the temperature to 65°C, and heat and stir for 12 hours.

[0029] Step 3: Cool the reaction mixture to room temperature, spin dry, separate by column chromatography and evaporate to dryness to obtain 15.6 g of fluorinated chalcone.

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 preparation method of fluoride chalcone. The preparation method comprises the following steps: firstly, mixing acetonitrile with methanol to obtain a reaction solvent; secondly, adding chalcone and an electrophilic fluorinating agent Selectfluor, and carrying out heating and stirring reaction; after the reaction is ended, generating yellow liquid, and filtering out white powder; heating to evaporate the reaction solvent, separating a reaction solution by a column chromatographic method, and drying to obtain a solid product fluoride chalcone of which the highest yield can reach 60 percent. The preparation method disclosed by the invention has the advantages of simplicity, directness, mild reaction conditions and no need of harsh reaction environment or metal catalyst; a main reaction can be finished by a one-step one pot method; a fluoride source is safe and environment-friendly and low in price, so that the synthesis cost is greatly reduced; the preparation method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and relates to a preparation method of fluorinated chalcones, in particular to a method for preparing fluorinated chalcones by directly fluorinating chalcones by a direct method. Background technique [0002] Fluorine is the most electronegative element in nature, and its atomic radius is closest to hydrogen atom. The electronic effect, hindering effect, pseudo-imitation effect, and penetration effect of fluorine atoms and fluorine-containing substituents are often used in drug design. The presence of fluorine in drug molecules can enhance binding force, change physicochemical properties, improve metabolic stability and reaction selectivity. Chalcones and their derivatives are products of cross-aldol condensation of aromatic aldehydes and ketones. Its chemical name is 1,3-diphenylpropenone. Compounds based on it exist in many natural plants such as licorice and safflower. In the body, it is th...

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): C07C45/63C07C49/813
CPCC07C45/63C07C49/813
Inventor 张斌易文斌
Owner NANJING UNIV OF SCI & TECH
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