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Preparation of symmetrical disulfide bond-bearing compound

A compound and disulfide bond technology, applied in the preparation of hydrogenated polysulfides/polysulfides, organic chemistry, etc., can solve the problems of expensive, complex, complicated reactions, etc., and achieve low cost, high yield, and simple and easy-to-obtain raw materials. Effect

Inactive Publication Date: 2009-07-08
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Using the above method to prepare symmetrical disulfide bond-containing compounds, some of the raw materials or catalysts used are more complicated, such as 1,3-dibromo-5,5-dimethylhydantoin; Obtain, as tetraphenyliron porphyrin catalyst, DMSO complexed molybdenum dioxide catalyst, and the reaction is more complicated, the cost of preparation method increases greatly, makes these methods limited in practical application

Method used

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  • Preparation of symmetrical disulfide bond-bearing compound
  • Preparation of symmetrical disulfide bond-bearing compound
  • Preparation of symmetrical disulfide bond-bearing compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] n-dodecanethiol thiosulfur coupling reaction:

[0068] Add 0.200g (0.988mmol) of n-dodecanethiol into a 50mL Schlenk container, vacuum-dry for 45 minutes, fill with high-purity argon, add 10mL of anhydrous ether with a syringe, cool to -80~-75°C, Add 0.46mL n-hexane solution with a concentration of 2.57mol / L n-butyllithium dropwise with a syringe (the content of n-butyllithium is 1.1 equivalents), keep the reaction at -80~-75°C for 0.5 hours, add 0.399g (3 equivalents ) of anhydrous copper chloride, keep the reaction at -80~-75°C for 0.5 hours, slowly rise to -60~-55°C and keep the reaction for 1 hour, naturally rise to room temperature and keep the reaction for 8 hours; at 0~5°C Add water to quench the reaction, transfer the reaction system to a 250mL separatory funnel, separate the organic phase and the aqueous phase, extract the aqueous phase twice with 20mL ether, and combine the extract with the organic phase of the reaction product; separate the combined organic p...

Embodiment 2

[0070] Thiophenol sulfur sulfur coupling reaction:

[0071] Add 0.200g (1.82mmol) of thiophenol into a 50mL Schlenk container, vacuum-dry for 45 minutes, fill with high-purity argon, add 10mL of anhydrous ether with a syringe, cool to -80~-75°C, and use a syringe to Add dropwise 0.79mL n-hexane solution with a concentration of 2.73mol / L n-butyllithium (the content of n-butyllithium is 1.1 equivalents), keep the reaction at -80~-75°C for 0.5 hours, add 0.789g (3 equivalents) of Anhydrous copper chloride, keep the reaction at -80~-75°C for 0.5 hours, slowly rise to -60~-55°C and keep the reaction for 1 hour, naturally rise to room temperature and keep the reaction for 8 hours; add water at 0~5°C to quench To quench the reaction, transfer the reaction solution into a 250mL separatory funnel, separate the organic phase and the aqueous phase, extract the aqueous phase three times with 20mL ether, and combine the extract with the organic phase of the reaction product; separate the c...

Embodiment 3

[0073] 4-Methylthiophenol sulfur-sulfur coupling reaction:

[0074] Add 0.200g (1.61mmol) of 4-methylthiophenol into a 50mL Schlenk container, vacuum-dry for 45 minutes, fill with high-purity argon, add 10mL of anhydrous tetrahydrofuran with a syringe, and cool to -78~-73 ℃, use a syringe to drop 0.69mL n-hexane solution with a concentration of 2.57mol / L n-butyllithium (the content of n-butyllithium is 1.1 equivalent), keep the reaction at -78~-73℃ for 0.6 hours, add 0.649g ( 3 equivalents) of anhydrous copper chloride, keep the reaction at -78~-73°C for 0.6 hours, slowly rise to -58~-53°C and keep the reaction for 1.2 hours, naturally rise to room temperature and keep the reaction for 8.5 hours; Add water at 7°C to quench the reaction, transfer the reaction system to a 250mL separatory funnel, separate the organic phase and the aqueous phase, extract the aqueous phase twice with 20mL chloroform, and combine the extract with the organic phase of the reaction product; The phas...

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Abstract

The invention discloses a method for preparing symmetrical compounds containing disulfide bonds. The method comprises: firstly, taking thioalcohol or phenylsulfhydrate as a raw material, utilizing metal alkyl compounds to seize reactive hydrogen on the thioalcohol or the phenylsulfhydrate at a temperature of between 60 DEG C below zero and 80 DEG C below zero and obtaining sulfur anions; secondly, using anhydrous cupric chloride for oxidation coupling to generate the disulfide bond; and thirdly, purifying reaction products and obtaining the symmetrical compounds containing the disulfide bonds. The preparation method has high yield and low cost, is simple and easy to obtain the adopted raw material, and is an effective path for preparing the symmetrical compounds containing the disulfide bonds.

Description

technical field [0001] The invention relates to a preparation method of a disulfide bond-containing compound, in particular to a preparation method of a symmetrical disulfide bond-containing compound, and belongs to the technical field of organic synthesis. Background technique [0002] Disulfide bond, also known as S—S bond, is a chemical bond between sulfur atoms in the form of —S—S—formed by oxidation of two -SH groups. In the field of biochemistry, generally refers to bonds among cysteine ​​residues in peptide and protein molecules. Disulfide bonds play an important role in the folding and stability of some proteins, and play an important role in the formation of the three-dimensional structure of protein molecules. According to the symmetry of the product, it is mainly divided into symmetrical disulfide bond-containing compounds and asymmetric disulfide bond-containing compounds. At present, there are many organic synthesis methods for related symmetrical disulfide bo...

Claims

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Application Information

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IPC IPC(8): C07C319/24C07C321/14C07C321/28C07C323/20C07C323/09
Inventor 王华田新勇王治华李春丽吴伟徐莉史建武
Owner HENAN UNIVERSITY
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