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Asymmetric trisulfide compound and synthesis method and application thereof

A synthesis method and compound technology, which are applied in the field of asymmetric trisulfide compounds and their synthesis, can solve the problems of low efficiency of trisulfide reagents, reduced reagent practicability, low boiling point, etc., and achieve mild conditions, high reaction efficiency, and simple reaction operations Effect

Inactive Publication Date: 2019-08-13
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, there are very few methods for synthesizing asymmetric trisulfides. The most traditional construction method is to start with phthalimide and synthesize azathiosulfides through a two-step reaction. Azathiosulfides and The mercaptan reaction can synthesize trisulfides. In the process of synthesizing azathiosulfides, phthalimide with a larger molecular weight needs to be used, and the unstable, low boiling point and highly corrosive raw material dichloro sulfide, the above factors reduce the practicality of the reagent
And the efficiency of this method synthesis trisulfide reagent is lower under most conditions

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Synthesis of compound 3a:

[0053]

[0054] Under nitrogen atmosphere, 1a (42.3mg, 0.2mmol), isopropyl mercaptan 2a (20.5uL, 0.22mmol), B(C 6 f 5 ) 3 (2.6mg, 0.005mmol), dichloromethane (2.0mL), the reaction system was stirred at room temperature for 5 hours, after the reaction was completed, dichloromethane was diluted, the solvent was removed, and column chromatography gave colorless liquid compound 3a (40.9mg, 80%). 1 H NMR (400MHz, CDCl 3 )δ7.62(d, J=8.3Hz, 2H), 7.43(d, J=8.3Hz, 2H), 4.07(s, 2H), 3.15(tt, J=6.8Hz, J=6.8Hz, 1H) ,1.33(d,J=6.8Hz,6H); 13 C NMR (100MHz, CDCl 3 )δ142.3, 132.3, 130.1, 118.7, 111.2, 42.2, 41.8, 22.4; IR (film) 2962, 2922, 2862, 2228, 1919, 1606, 1503, 1446, 1235, 1153, 1047, 875, 842, 741, 652) CalcMS ( for C 11 h 13 NS 3 255.0210,Found 255.0213.

Embodiment 2

[0056] Synthesis of compound 3a:

[0057]

[0058] Under nitrogen atmosphere, 1a (42.3mg, 0.2mmol), isopropyl mercaptan 2a (20.5uL, 0.22mmol), B(C 6 f 5 ) 3 (2.6mg, 0.005mmol), dichloromethane (2.0mL), and 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 colorless liquid compound 3a (15.3mg ,30%).

Embodiment 3

[0060] Synthesis of compound 3b:

[0061]

[0062] Under nitrogen atmosphere, 1a (42.3mg, 0.2mmol), n-butyl mercaptan 2b (23.5uL, 0.22mmol), B(C 6 f 5 ) 3 (2.6mg, 0.005mmol), dichloromethane (2.0mL), the reaction system was stirred at room temperature for 5 hours, after the reaction was completed, dichloromethane was diluted, the solvent was removed, and column chromatography gave colorless liquid compound 3b (47.2mg, 88%). 1 H NMR (400MHz, CDCl 3 )δ7.62(d, J=8.1Hz, 2H), 7.43(d, J=8.1Hz, 2H), 4.07(s, 2H), 2.81(t, J=7.3Hz, 2H), 1.84–1.55( m,2H),1.57–1.30(m,2H),0.92(t,J=7.4Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ 142.3, 132.3, 130.1, 118.7, 111.3, 42.1, 38.5, 30.7, 21.5, 13.6. .HRMS(EI) Calcd for C 12 h 15 NS 3 269.0367,Found 269.0371.

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Abstract

The invention discloses a synthesis method of an asymmetric trisulfide compound shown in a formula (3). With an overcuring reagent R<1>SSOMe shown in a formula (1) and an organic sulfur alcohol compound shown in a formula (2) as raw reaction materials, under the effect of a catalyst, through a reaction, the asymmetric trisulfide compound is obtained. According to the method, the reaction conditions are mild, the raw materials are 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 not need to be added, and the method is environmentally friendly; a reaction substrate is easy to prepare; after reaction amplification, the reaction efficiency is high. Organic sulfur alcohol in the formula (2) can be a polypeptide compound with sulfur alcohol. A method for overcuring modification on polypeptides is provided. The method has wide application prospects andhigh practical value.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to asymmetric trisulfide compounds and their synthesis method and application. Background technique [0002] Organic compounds containing trisulfide structures are a very important class of compounds, and trisulfide compounds widely exist in natural products, especially marine natural products, such as the famous Epidithiodiketopiperazines (ETPs) class of natural products (shown below). And trisulfide also has a good application in material chemistry. It is found that trisulfide compound shows higher efficiency than disulfide as the cathode material of rechargeable lithium battery. In addition, polysulfides are common lubricating oil additives, mainly as gear oils. Therefore, it is particularly important to find a persulfide reagent with mild conditions, simple operation and wide substrate range to construct trisulfide compounds. [0003]...

Claims

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Application Information

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IPC IPC(8): C07C323/56C07C319/24C07F7/18C07D241/12C07C323/58C07C323/52C07H13/04C07H1/00
CPCC07C323/56C07C319/24C07D241/12C07C323/58C07C323/52C07H13/04C07H1/00C07F7/1804
Inventor 姜雪峰薛佳晖肖霄
Owner EAST CHINA NORMAL UNIVERSITY
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