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

Asymmetric disulfide compound and synthesis method and application thereof

A synthetic method and asymmetric technology, applied in the field of asymmetric disulfide compounds and their synthesis, can solve the problems of environmental and human injury, easy to be oxidized, poisoning of metal catalysts, etc., and achieve the effect of solving electrophilic persulfide reagents

Inactive Publication Date: 2019-08-13
EAST CHINA NORMAL UNIV
View PDF0 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this type of method, the organic mercaptan or thiophenol compound used is easily oxidized and has a poisonous effect on the metal catalyst; the taste of the raw material is too heavy, and it has different degrees of damage to the environment and the human body; the application of this type of method restricted

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
  • Asymmetric disulfide compound and synthesis method and application thereof
  • Asymmetric disulfide compound and synthesis method and application thereof
  • Asymmetric disulfide compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Synthesis of compound 3a:

[0084]

[0085] Under air atmosphere, 1a (42.1mg, 0.2mmol), indole (35.1mg, 0.3mmol), methanesulfonic acid (2.0mg, 0.02mmol), tert-amyl alcohol (0.5mL) were successively added to the reaction tube, and the reaction system Stirring at 0°C for 5 hours, after the reaction was completed, dichloromethane was diluted, the solvent was removed, and column chromatography gave white solid compound 3a (46.0 mg, 78%). 1 H NMR (400MHz, CDCl 3 )δ8.47(s,1H),7.83-7.81(m,1H),7.38-7.34(m,2H),7.31–7.17(m,2H),4.12(q,J=7.1Hz,2H),2.76 (t, J=7.0Hz, 2H), 2.41(t, J=7.3Hz, 2H), 2.10(p, J=7.2Hz, 2H), 1.24(t, J=7.1Hz, 3H); 13 C NMR (100MHz, CDCl 3 )δ173.12,136.28,128.59,123.14,121.03,119.51,111.56,10806,60.39,37.54,32.73,23.77,14.22.IR(film)3398,2926,1714,1497,14753,1411,373,137,1 ,1131,1095,1035,745. HRMS (EI) Calcd for C 15 h 19 NO 2 S 2 295.0701,Found 295.0705.

Embodiment 2

[0087] Synthesis of compound 3a:

[0088]

[0089] Under air atmosphere, 1a (42.1mg, 0.2mmol), indole (35.1mg, 0.3mmol), camphorsulfonic acid (4.6mg, 0.02mmol), 1,2-dichloroethane (0.5 mL), the reaction system was stirred at 0°C for 5 hours, after the reaction was completed, dichloromethane was diluted, the solvent was removed, and column chromatography gave white solid compound 3a (29.5mg, 50%).

Embodiment 3

[0091] Synthesis of compound 3a:

[0092]

[0093]Under air atmosphere, add 1a (42.1mg, 0.2mmol), indole (35.1mg, 0.3mmol), o-nitrobenzenesulfonic acid (4.1mg, 0.02mmol), 1,2-dichloroethyl Alkane (0.5mL), the reaction system was stirred at 0°C for 5 hours, after the reaction was completed, dichloromethane was diluted, the solvent was removed, and column chromatography gave white solid compound 3a (30.7mg, 52%).

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 synthesis method of an asymmetric disulfide compound shown in a formula (3). With an overcuring reagent RSSOMe shown in a formula (1) and nucleophilic reagents (2) and (4) asraw reaction materials, under the effect of a catalyst, through a reaction, the asymmetric disulfide compound is obtained. According to the method, the reaction conditions are mild, the raw materialsare low in price and easy to obtain, the reaction operation is simple, the yield is high, the metal catalysts are not needed in the reaction, an additional oxidizing agent or reducing agent does notneed to be added, and the method is environmentally friendly; a reaction substrate is easy to prepare; after reaction amplification, the reaction efficiency is high. The reaction in the method can beapplied to overcuring modification on benzazole and (+)-delta-tocopherol. The method has wide application prospects and high practical value.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to asymmetric disulfide compounds and their synthesis method and application. Background technique [0002] Organic compounds containing persulfur structures are a very important class of compounds, which widely exist in natural products, medicines, materials, and food additives. Therefore, a persulfur reagent construction process with mild conditions, simple operation, and a wide range of substrates has been found. Sulfur compounds are particularly important. [0003] In the prior art, the traditional method for synthesizing asymmetric disulfide compounds is mainly to prepare one thiol or thiophenol compound with another thiol or thiophenol compound and its derivatives. In this type of method, the organic mercaptan or thiophenol compound used is easily oxidized and has a poisonous effect on the metal catalyst; the taste of the raw materia...

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): C07D209/30C07D207/36C07H13/04C07H15/04C07H1/00C07C323/56C07D311/58C07C323/22C07C323/52C07C323/59C07C319/22C07C381/00
CPCC07D209/30C07D207/36C07H13/04C07H15/04C07H1/00C07C323/56C07D311/58C07C323/22C07C323/52C07C323/59C07C381/00C07C2601/16
Inventor 姜雪峰薛佳晖肖霄
Owner EAST CHINA 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

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