Asymmetric disulfide compound and synthesis method and application thereof
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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
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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 t
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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%).
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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...
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