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

Preparation method of compound containing non-terminal-group double bonds

A compound, the technology of diacyl peroxide, applied in the preparation of organic compounds, the preparation of amino compounds and steroids from amines, etc., can solve the problems of hindering aliphatic peroxyacetyl compounds, difficult to control, etc., and achieve raw materials and catalysts. Inexpensive, efficient reaction, mild reaction conditions

Active Publication Date: 2017-10-20
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
View PDF0 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As we all know, the thermal decomposition methods of dibasic acyl peroxides are diverse and complex, and various products will be produced at the same time when heated
The dibasic acyl peroxide itself is also easily decomposed into a variety of free radical fragments, and it is not easy to control
These aspects have prevented aliphatic peroxyacetyl compounds from becoming versatile and practical chemical reagents in organic reactions

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 compound containing non-terminal-group double bonds
  • Preparation method of compound containing non-terminal-group double bonds
  • Preparation method of compound containing non-terminal-group double bonds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059]

[0060] Add 58 μL (0.5 mmol) styrene 1-1, 600 mg (1.5 mmol,) lauroyl peroxide 1-2, 10 mol% catalyst Pd(OAc) to the reaction tube 2 , solvent toluene 2mL, add a magnetic stirrer, and then put it into a 90°C oil bath for 3 hours of reaction. After the reaction, cool to room temperature, dilute with ethyl acetate, filter with diatomaceous earth, evaporate and concentrate under reduced pressure to remove the solvent, the crude product is separated by column chromatography, the obtained product sample is recorded as 1-3, a total of 92.88mg, and the yield is 72% .

[0061] The NMR detection data of product samples 1-3 are as follows:

[0062] 1 H NMR (400MHz, CDCl 3 )δ7.34(d, J=7.2Hz, 2H), 7.28(t, J=7.2Hz, 2H), 7.18(t, J=7.2Hz, 1H), 6.37(d, J=15.8Hz, 1H) , 6.26-6.18 (m, 1H), 2.22-2.17 (m, 2H), 1.47-1.42 (m, 2H), 1.30-1.26 (m, 16H), 0.88 (t, J=6.8Hz, 3H).

[0063] 13 C NMR (100MHz, CDCl 3 )δ 137.99, 131.29, 129.69, 128.47, 126.74, 125.91, 33.09, 31.96, 29.71, 29.68,...

Embodiment 2

[0065]

[0066] Add 23 μL (0.2 mmol) styrene 2-1, 240 mg (0.6 mmol) lauroyl peroxide 2-2, 10 mol% catalyst Pd(TFA) to the reaction tube 2 , solvent tetrahydrofuran 1mL, add a magnetic stirrer, and then put it into a 90 ° C oil bath for 3 hours of reaction. After the reaction, cool to room temperature, dilute with ethyl acetate, filter with diatomaceous earth, and concentrate under reduced pressure to remove the solvent. The crude product is separated by column chromatography. .

[0067] The NMR detection data of product sample 2-3 are basically the same as the NMR detection data of product sample 1-3.

Embodiment 3

[0069]

[0070] Add 298.5 mg (0.75 mmol) lauroyl peroxide 3-2, 58 μL (0.5 mmol) styrene 3-1, 5 mol% catalyst Fe(OTf) to the reaction tube 3 , solvent tetrahydrofuran 2ml, add a magnetic stirrer, and then put it into a 60 ° C oil bath for 3 hours of reaction. After the reaction, cool to room temperature, dilute with ethyl acetate, filter with diatomaceous earth, and concentrate under reduced pressure to remove the solvent. The crude product is separated by column chromatography. .

[0071]The NMR detection data of the product sample 3-3 are basically the same as the NMR detection data of the product sample 1-3.

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 provides a preparation method of a compound III. The preparation method is characterized in that diacyl peroxide I and a compound II containing carbon-carbon double bonds are subjected to a coupling reaction in the presence of catalysts to produce the compound III. The diacyl peroxide is introduced into a Heck reaction as an efficient and controllable alkylating agent for the first time in the method, and the method has the advantages that raw materials and catalysts are cheap, the reaction condition is mild, the operation is simple, the reaction is efficient and the like.

Description

technical field [0001] The invention relates to a preparation method of a compound containing a non-terminal double bond, belonging to the field of organic synthesis. Background technique [0002] In the 1960s and 1970s, American chemist Heck and Japanese chemist Mizoroki discovered and developed the Heck reaction and made a lot of pioneering work. Heck also shared the 2010 Nobel Prize in Chemistry with Japanese chemists Negihi and Suzuki . This reaction and other transition metal-catalyzed cross-coupling reactions have revolutionized the field of organic chemistry and have become powerful tools in organic synthesis. The reactions between electrophiles without β hydrogens (such as aryl, vinyl, benzyl halides, or sulfonates) and alkenes have been well studied. However, the Heck reaction of β-hydrogen-containing alkyl electrophiles still faces great challenges. It mainly comes from the relatively slow oxidative addition process of the alkyl electrophile and the fast β-hydro...

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): C07C15/44C07C15/50C07C15/58C07C13/465C07C13/43C07C11/12C07C2/88C07C22/04C07C22/08C07C25/24C07C17/263C07C69/145C07C67/293C07C43/215C07C41/30C07C63/64C07C51/353C07C211/27C07C209/68C07C69/618C07C67/343C07J1/00
CPCC07C2/88C07C17/263C07C41/30C07C51/353C07C67/293C07C67/343C07C209/68C07J1/0011C07C15/44C07C15/50C07C15/58C07C13/465C07C13/43C07C11/12C07C22/04C07C22/08C07C25/24C07C69/145C07C43/215C07C63/64C07C211/27C07C69/618
Inventor 鲍红丽简武军葛亮陈绍维冯薇薇
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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