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

Synthesis method of new ligand for efficient catalysis of CuAAC reaction

A synthesis method and reaction technology, applied in the field of synthesis of functional structural molecules, can solve the problems of harsh reaction conditions, insufficient research and development requirements for ligands, difficult synthesis, etc., and achieve obvious effects.

Inactive Publication Date: 2018-01-26
HENAN NORMAL UNIV
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In recent years, although compounds with one-valent copper ligands have been reported one after another, the demand for ligand research and development is far from enough for the wide application of click reactions.
In the past, for the synthesis of such ligands, the synthesis conditions often required expensive reaction raw materials, it was difficult to synthesize in large quantities, and the reaction conditions were relatively harsh.

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
  • Synthesis method of new ligand for efficient catalysis of CuAAC reaction
  • Synthesis method of new ligand for efficient catalysis of CuAAC reaction
  • Synthesis method of new ligand for efficient catalysis of CuAAC reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014]

[0015] To synthesize glycine methyl ester TMS-diyne, add glycine methyl ester hydrochloride 2mmol trimethylsilyl acetylene 5mmol, mass concentration 5mmol of formaldehyde aqueous solution 5mmol, sodium bicarbonate 5mmol and cuprous chloride 0.2 in a round bottom flask mmol, mixed and stirred at 35°C for 18 hours, and the reaction process was monitored by TLC. After the reaction was completed, it was extracted three times with dichloromethane / water, and the organic phase was washed and dried, and the yield was 92%. The product is a colorless liquid. To synthesize glycine methyl ester diyne, add glycine methyl ester TMS-diyne 2mmol in 5mL tetrahydrofuran solution in a round bottom flask, then add tetrabutylammonium fluoride 5mmol in batches, mix and stir at room temperature for 3 hours, and monitor the reaction process by TLC . After the reaction was finished, it was extracted three times with dichloromethane / water, and the organic phase was washed and dried, and t...

Embodiment 2

[0017]

[0018]

[0019] In a 10mL round bottom flask, add 1mmol glycine methyl ester diyne, 2mmol phenyl azide, 1.2mmol K 2 CO 3 and 0.1mmol cuprous iodide, mixed and stirred at room temperature in acetonitrile and water solvent for 10 hours, the reaction process was detected by TLC, extracted with ethyl acetate after the reaction, and separated by silica gel column chromatography to obtain the target product, the yield was 85% .

Embodiment 3

[0021]

[0022] In a 10mL round bottom flask, add 1mmol glycine methyl ester diyne, 2mmol p-trifluoromethylphenyl azide, 1.2mmol K 2 CO 3 and 0.1mmol cuprous iodide, mixed and stirred in acetonitrile and water solvent at room temperature for 12 hours, the reaction process was detected by TLC, extracted with ethyl acetate after the reaction, and separated by silica gel column chromatography to obtain the target product with a yield of 80%.

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

Belonging to the technical field of synthesis of functional structural molecules, the invention discloses a synthesis method of a new ligand for efficient catalysis of CuAAC reaction. The key point ofthe technical scheme adopted by the invention lies in that: the synthesis method of the new ligand for efficient catalysis of CuAAC reaction includes: firstly synthesizing glycine methyl ester diyne,then taking glycine methyl ester diyne, an azido compound, K2CO3 and copper iodide as the raw materials, using acetonitrile and water as the solvent, carrying out stirring reaction at room temperature, and performing post-treatment at the end of reaction, thus obtaining the new ligand glycine methyl ester 1, 2, 3-ditriazole ring opening compound. The invention provides a variety of novel, efficient and easily available ligand catalysts for click reaction, as a ligand, the compound synthesized by the method provided by the invention has obvious effect of accelerating reaction and has a very practical application.

Description

technical field [0001] The invention belongs to the technical field of synthesizing functional structural molecules, and in particular relates to a synthesis method of a novel ligand that efficiently catalyzes CuAAC reaction. Background technique [0002] The Nobel Prize winner in Chemistry Sharpless, a chemist from the Scripps Research Institute in the United States, proposed the concept of "click" chemistry in 2001. Once the concept was proposed, it attracted widespread attention and became a hot spot of common concern in various disciplines of chemistry, life, medicine and materials at home and abroad. one. How to improve the biocompatibility of the click reaction and reduce the amount of Cu(I) has become a new trend of current research. [0003] There are two important research fields in click chemistry work today: one is copper-free catalyzed SPAAC reactions, and the other is ligand compounds that can coordinate and promote monovalent copper ions. The ligand has a ver...

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): C07D249/06
Inventor 李凌君邢晓芳尚同鹏黄申龙
Owner HENAN NORMAL UNIV
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