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A kind of synthetic method of unsymmetrical thioether

A synthetic method and asymmetric technology, applied in the formation/introduction of thiol/thioether group, thioether preparation, chemical instruments and methods, etc., can solve problems such as restricting practical application

Active Publication Date: 2018-01-19
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] It can be seen that the current method for synthesizing asymmetric thioethers inevitably uses highly toxic, foul-smelling, sensitive and perishable thiol compounds in the reaction process, and requires expensive metal catalysts and harsh reaction conditions (anhydrous, anaerobic). etc.), these shortcomings seriously restrict the practical application of this method

Method used

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  • A kind of synthetic method of unsymmetrical thioether
  • A kind of synthetic method of unsymmetrical thioether
  • A kind of synthetic method of unsymmetrical thioether

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preparation example Construction

[0036] The invention provides a kind of synthetic method of unsymmetrical thioether, comprises the following steps:

[0037]a), under the catalytic conditions of tetrabutylammonium halide, the compound of formula (I), the compound of formula (II) and oxysulfide are reacted in a solvent to obtain the asymmetric thioether with the structure of formula (III);

[0038]

[0039] Among them, R 1 selected from phenyl, substituted phenyl, naphthyl, substituted naphthyl, thienyl or substituted thienyl, R 2 selected from hydrogen, phenyl, substituted phenyl, naphthyl, substituted naphthyl, thienyl, or substituted thienyl; or R 1 , R 2 Form a fluorene ring or a thioxanthene ring with the C connected to it;

[0040] R 3 selected from hydrogen or alkyl;

[0041] R 4 selected from hydrogen, phenyl, substituted phenyl, naphthyl, substituted naphthyl, thienyl or substituted thienyl, R 5 selected from hydrogen; or R 4 , R 5 Form a fluorene ring or a thioxanthene ring with the C con...

Embodiment 1

[0068] Synthesis of 4-((3,3-diarylallylthio)methyl)benzonitrile

[0069] Weigh 0.3mmol 1,1-diphenylprop-2-enyl-1-ol (0.0631 grams), 0.6mmol p-cyanobenzyl chloride (0.0910 grams), 0.72mmol sodium thiosulfate (0.1138 grams), 0.06 Mmol tetrabutylammonium iodide (0.0222 grams), in a 20mL test tube reaction tube, add 1mL water as a solvent, seal and seal, stir and react at 80°C for 5 hours; Sodium sulfate water drying and column chromatography separation (column chromatography separation conditions: the stationary phase is 300-400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase change program (A:B ) was 1:20→1:6), and 0.0778 gram of reaction product was obtained.

[0070] The above-mentioned reaction product is characterized, and the result is:

[0071] 1 H NMR (400MHz, CDCl 3 ):δ=7.49–7.42(m,2H),7.38–7.33(m,3H),7.29–7.25(m,3H),7.22–7.18(m,2H),7.18–7.13(m,4H),6.08 (t, J=7.8Hz, 1H), 3.63(s, 2H), 3.18(d, J=7.8Hz, 2H)ppm;

...

Embodiment 2

[0074] Synthesis of 4-((3,3-bis(4-fluorophenyl)allylthio)methyl)benzonitrile

[0075] Weigh 0.3mmol 1,1-bis(4-fluorophenyl)prop-2-enyl-1-ol (0.0739 grams), 0.6mmol p-cyanobenzyl chloride (0.0910 grams), 0.72mmol sodium thiosulfate ( 0.1138 grams), 0.06mmol tetrabutylammonium iodide (0.0222 grams), in a 20mL test tube reaction tube, add 1mL water as a solvent, seal and seal, stir and react at 80°C for 5 hours; after the reaction, the reaction solution is passed through Ethyl acetate, anhydrous sodium sulfate drying and column chromatography separation (column chromatography separation conditions: the stationary phase is 300-400 mesh silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), the mobile phase changes The procedure (A:B) is 1:20 → 1:6), yielding 0.0932 g of reaction product.

[0076] The above-mentioned reaction product is characterized, and the result is:

[0077] 1 H NMR (400MHz, CDCl 3 ):δ=7.51(d, J=8.3Hz, 2H), 7.24(d, J=8.2Hz, 2H), 7...

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Abstract

The invention belongs to the field of chemistry, and relates to a synthetic method of an unsymmetrical thioether, comprising the following steps: a), under the catalytic conditions of tetrabutylammonium halide, formula (I) structure compound, formula (II) structure compound and sulfur oxide The salt is reacted in a solvent to obtain an asymmetric thioether having a structure of formula (III); wherein, R1 is selected from phenyl, substituted phenyl, naphthyl, substituted naphthyl, thienyl or substituted thienyl, and R2 is selected from hydrogen , phenyl, substituted phenyl, naphthyl, substituted naphthyl, thienyl or substituted thienyl; or R1, R2 and the C they are connected to form a fluorene ring or a thioxanthene ring; R3 is selected from hydrogen or alkyl; R4 is selected from Hydrogen, phenyl, substituted phenyl, naphthyl, substituted naphthyl, thienyl or substituted thienyl, R5 is selected from hydrogen; or R4, R5 and its connected C form a fluorene ring or thioxanthene ring; R6 is selected from alkyl Or substituted alkyl; X is selected from Cl, Br or I.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a method for synthesizing an unsymmetrical thioether. Background technique [0002] Asymmetric thioethers are an important class of sulfur-containing compounds. Their skeletons not only widely exist in natural products and active pharmaceutical molecules, but also can be used as advanced materials and metal ligands, and are also important intermediates in organic synthesis. [0003] Asymmetric thioether compounds are widely used in biomedicine, such as: [0004] Methionine (Methionine) is one of the essential amino acids that make up the human body. It is involved in protein synthesis. Because it cannot be produced in the body itself, it must be obtained from the outside. The lack of methionine will lead to the blockage of protein synthesis in the body and cause damage to the body. . At present, methionine is mostly synthesized by the coupling reaction of halides, thiols and re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/56C07D335/12C07D333/16C07C323/07C07C321/20C07C321/22C07D209/08C07H9/04C07H1/00C07C323/52C07C323/54
CPCC07C319/14C07D209/08C07D333/16C07D335/12C07H1/00C07H9/04C07C323/56C07C323/07C07C321/20C07C321/22C07C323/52C07C323/54C07D333/18C07C323/60C07B45/06C07C321/12C07C319/28C07C321/18C07C2527/12C07F11/005
Inventor 纪顺俊褚雪强徐小平曹文斌
Owner SUZHOU UNIV
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