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

Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt

A metal copper salt, a technology for catalytic preparation, which is applied in chemical instruments and methods, formation/introduction of mercapto/thioether groups, preparation of thioethers, etc., to achieve the effects of cheap and easy-to-obtain reaction raw materials, simple preparation methods, and diverse product structures

Inactive Publication Date: 2012-02-15
ZHEJIANG UNIV
View PDF7 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, in the preparation method of (Z)-1,2-disulfide-1-alkenes disclosed with practical value, so far, there is still no use of this simple and convenient method to prepare this type of important organic compound compound

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
  • Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt
  • Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt
  • Method for preparing (Z)-1,2-disulfide-1-olefin by catalysis of metal copper salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Under the protection of nitrogen, add (Z)-1-bromo-2-p-methylphenylsulfide-1-decene 171mg, Cs to the reaction tube 2 CO 3 326mg, Cu 2 O 7mg, DMEDA 8μL, p-methylthiophene 124mg, DMF 2mL, mix well, react at 120°C for 24h. After the reaction, it was cooled to room temperature, and then 15 mL of water was added to the reactant, extracted with ethyl acetate, dried with anhydrous sodium sulfate, concentrated, and passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 50:1) to obtain The product (Z)-1,2-dimethylphenylsulfide-1-decene, the resulting product is 157 mg, and the yield is 82%. 1 H NMR(400MHz, CDCl 3 ): δ7.32-7.27(m, 4H), 7.13-7.08(m, 4H), 6.45(s, 1H), 2.32(s, 3H), 2.31(s, 3H), 2.20(t, J=7.2 Hz, 2H), 1.49-1.46 (m, 2H), 1.29-1.20 (m, 10H), 0.87 (t, J=6.8 Hz, 3H); 13 C NMR(100MHz, CDCl 3 ): δ137.12, 137.11, 134.7, 132.8, 131.5, 130.4, 130.3, 130.1, 130.0, 128.8, 37.2, 32.1, 29.6, 29.5, 29.1, 28.8, 22.9, 21.4, 21.3, 14.4.

Embodiment 2

[0027]

[0028] Under the protection of nitrogen, add (Z)-1-bromo-2-p-methylphenylsulfide-1-decene 171mg, Cs to the reaction tube 2 CO 3 326mg, Cu 2 O 7mg, TMEDA 15μL, p-cresol 124mg, DMF 2mL, react at 120°C for 24h. Cool to room temperature, add 15 mL of water, extract with ethyl acetate, dry with anhydrous sodium sulfate, concentrate, and pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 50:1) to obtain product (Z)-1, 2 -Di-p-methylphenyl sulfide-1-decene, the resulting product is 148 mg, and the yield is 77%.

Embodiment 3

[0030]

[0031] Under the protection of nitrogen, add (Z)-1-bromo-2-p-methylphenylsulfide-1-decene 171mg, Cs to the reaction tube 2 CO 3 326mg, Cu 2 O 7mg, DMEDA 8μL, p-toluol 124mg, THF 2mL, react at 120°C for 24h. Cool to room temperature, add 15 mL of water, extract with ethyl acetate, dry with anhydrous sodium sulfate, concentrate, and pass through a silica gel column (the volume ratio of petroleum ether to ethyl acetate is 50:1) to obtain product (Z)-1, 2 -Di-p-methylphenyl sulfide-1-decene, the resulting product is 144 mg, and the yield is 75%.

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 method for preparing (Z)-1,2-disulfide-1-olefin by the catalysis of metal copper salt, comprising the following steps of: using metal copper salt as a catalyst and using (Z)-1-bromine-2-thioether-1-olefin or mercaptan as a substrate under the action of alkaline in an organic solvent to synthesize (Z)-1,2-disulfide-1-olefin. The invention has the following advantages: the raw materials in the method are easily available; the preparation method is simple; as the catalyst, the metal copper salt is cheap and easily available; (Z)-1,2-disulfide-1-olefin prepared by the method has an extensive application prospect in the fields of coordination chemistry, material science, organic synthesis and the like.

Description

Technical field [0001] The present invention relates to the field of organic synthesis, in particular to a method for preparing (Z)-1,2-disulfide-1-alkene by catalyzing a metal copper salt. Background technique [0002] (Z)-1,2-Disulfide-1-olefins are an important class of organic compounds, which have broad application prospects in coordination chemistry, materials science, and organic synthesis (Clemenson, PI in the literature The chemistry and solid State properties of nickel, palladium and platinum bis (maleonitriledithiolate) compounds. Coord. Chem. Rev. 1990, Kondo, T. etc. in the literature Metal-Catalyzed Carbon-Sulfur Bond Formation. Chem. Rev. 2000 and Zyk, NV, etc. It is reported in Methods for the synthesis of vinyl sulfides. Russ. Chem. Rev. 2003). [0003] There are two traditional methods for preparing the compound: 1) the addition of metal-catalyzed disulfide compounds to alkyne; 2) the addition of mercaptans or thiophenol compounds to alkyne sulfides. These two m...

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): C07B45/06C07C319/14C07C321/28C07D333/34C07D213/70C07F15/00
Inventor 陈万芝徐辉夏钦钦
Owner ZHEJIANG 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

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