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Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric persulfide compound and synthesis method thereof

A synthesis method and asymmetric technology, applied in the field of organic compound process application, can solve the problems of irritating odor, easy oxidation of sulfurized reagents, expensive catalyst, etc., and achieve the effects of no irritating odor, efficient reaction and mild conditions.

Active Publication Date: 2016-06-29
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example: vulcanizing reagents are easy to oxidize, easy to poison metal catalysts and have a pungent smell, poor selectivity in the oxidation process, and expensive catalysts

Method used

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  • Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric persulfide compound and synthesis method thereof
  • Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric persulfide compound and synthesis method thereof
  • Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric persulfide compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of 4-(4-methylphenyldithio)butyronitrile:

[0046]

[0047] 4-Chlorobutyronitrile (103.5mg, 1.0mmol, 5.0equiv.) and Na 2 S 2 o 3 ·5H 2 O (248.2mg, 1.0mmol, 5.0equiv.) was added to the reaction tube, and then the reaction solvent ethanol / water (0.25mL / 0.5mL) was added, and stirred at 100°C for 2 hours. Then the reaction system was cooled, and the solvent was removed under reduced pressure, then sodium p-toluenesulfinate (35.6 mg, 0.2 mmol, 1.0 equiv.) was added, and then the reaction solvent 1,4-dioxane (1.0 mL ), and stirred at reflux for 11 hours at a reaction temperature of 110°C. Then the reaction system was cooled to room temperature, and PPh was added 3 (31.5mg, 0.12mmol, 0.6equiv.) was reacted at 50°C for 4 hours, then the reaction solution was decompressed to remove the solvent, and the product 1 was obtained after separation by column chromatography (eluent polarity: petroleum ether / ethyl acetate ester 40:1). Yield: 94%; 1 HNMR (400MHz, CDCl...

Embodiment 2

[0049] Synthesis of 4-(4-methylphenyldithio)butyronitrile:

[0050]

[0051] 4-Chlorobutyronitrile (103.5mg, 1.0mmol, 5.0equiv.) and Na 2 S 2 o 3 ·5H 2 O (248.2mg, 1.0mmol, 5.0equiv.) was added to the reaction tube, and then the reaction solvent ethanol / water (0.25mL / 0.5mL) was added, and stirred at 100°C for 2 hours. Then the reaction system was cooled, and the solvent was removed under reduced pressure, then sodium p-toluenesulfinate (35.6 mg, 0.2 mmol, 1.0 equiv.) was added, and then the reaction solvent 1,4-dioxane (1.0 mL ), stirred at a reaction temperature of 90° C. for 11 hours. Then the reaction system was cooled to room temperature, and finally the solvent was removed from the reaction solution under reduced pressure, and the product 1 was obtained after separation by column chromatography (eluent polarity: petroleum ether / ethyl acetate 40:1). Yield: 72%;

Embodiment 3

[0053] Synthesis of 4-(4-methylphenyldithio)butyronitrile:

[0054]

[0055] 4-Chlorobutyronitrile (103.5mg, 1.0mmol, 5.0equiv.) and Na 2 S 2 o 3 ·5H 2 O (248.2mg, 1.0mmol, 5.0equiv.) was added to the reaction tube, and then the reaction solvent ethanol / water (0.25mL / 0.5mL) was added, and stirred at 100°C for 2 hours. Then the reaction system was cooled, and the solvent was removed under reduced pressure, then sodium p-toluenesulfinate (35.6 mg, 0.2 mmol, 1.0 equiv.) was added, and then the reaction solvent 1,4-dioxane (1.0 mL ), stirred at a reaction temperature of 70° C. for 11 hours. Then the reaction system was cooled to room temperature, and finally the solvent was removed from the reaction solution under reduced pressure, and the product 1 was obtained after separation by column chromatography (eluent polarity: petroleum ether / ethyl acetate 40:1). Yield: 37%;

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Abstract

The invention discloses a synthesis method of aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides as shown in a formula (II) or a formula (IV). According to the synthesis method, with sulfinic acid sodium salt, and halogenated hydrocarbon and Na2S2O3 as reaction materials or Bunte salt as a reaction material instead of the halogenated hydrocarbon and Na2S2O3, the aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides are obtained by reaction in the absence of transition metal. The synthesis method has the advantages that the reaction is efficient; the yield is high; a vulcanizing reagent is cheap, easily available, stable, and free of pungent smell; no strong acid or alkali or extra oxidizing or reducing agent is added in reaction; the condition is relatively mild; and no transition metal is used as a catalyst in the reaction, and therefore the method is economical, practical and friendly to the environment; a reaction substrate is easy to prepare; the reaction efficiency is high after the reaction is amplified, and therefore, the synthesis method has a wide application prospect and practical value.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and specifically relates to a class of aryl-aryl, aryl-alkyl, and alkyl-alkyl asymmetric persulfur compounds and an efficient and convenient synthesis method thereof. Background technique [0002] Organic compounds containing persulfur structures are widely found in biological structures and functional molecules. For example, vegetables such as garlic and onions, and marine organisms such as sea squirts contain persulfur organic compounds, and persulfur structures are found in human and animal peptides It plays an important role in the formation of primary and tertiary structures. Organic compounds containing persulfur are widely used in the synthesis of medicine, polymer materials, pesticides, flavors and flavors, and food additives. Compounds containing persulfur structures are used in the field of medicine. For example, the broad-spectrum antibacterial drug All...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/24C07C323/52C07C323/20C07C321/28C07C323/16C07C323/07C07C323/56C07C323/09C07C321/20C07C321/22C07C323/22C07C319/14C07D333/34C07J31/00
Inventor 姜雪峰肖霄冯明昊
Owner EAST CHINA NORMAL UNIV
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