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The preparation method of trisubstituted tetrahydrothiophene

A tetrahydrothiophene, tri-substituted technology, applied in the field of chemistry, achieves the effects of low cost, mild reaction conditions and wide substrate range

Inactive Publication Date: 2016-02-03
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, a large number of research reports have shown that the reaction requires the participation of catalysts such as triethylamine, polyacrylonitrile fibers, etc.

Method used

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  • The preparation method of trisubstituted tetrahydrothiophene
  • The preparation method of trisubstituted tetrahydrothiophene
  • The preparation method of trisubstituted tetrahydrothiophene

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Embodiment Construction

[0020] The preferred embodiments of the present invention will be described in detail below with reference to the accompanying drawings. The experimental methods for which specific conditions are not indicated in the preferred embodiments are usually carried out according to conventional conditions, or according to the conditions suggested by the reagent manufacturer.

[0021] 1. Optimization of Sulfa-Michale / Aldol series reaction conditions

[0022] The reaction of compound 1a (chalcone) with compound 2 (2,5-dihydroxyl,4-dithiane) was used as a model reaction.

[0023] 1. The effect of solvent and temperature on the Sulfa-Michale / Aldol series reaction

[0024] First, solvent screening was performed at 25°C without catalyst. The results are shown in Table 1. This model reaction can obtain better diastereoselective products in polar protic solvents such as ethanol, water, and isopropanol, especially in water. The dr value of its product can be greater than 99:1 (Seeing No. 1...

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Abstract

The invention discloses a preparation method of tri-substituted tetrahydrothiophene. The preparation method comprises the following steps: performing reflux reaction on a substrate and 2,5-dihydroxyl 1,4-dithiane in water in the absence of a catalyst to obtain corresponding tri-substituted tetrahydrothiophene, wherein the substrate is a chalcone compound shown in a general formula 1, alpha, beta unsaturated ketone shown in a general formula 5 or trans-beta-nitroolefin shown in a general formula 8. The method for preparing tri-substituted tetrahydrothiophene through catalyst-free Sulfa-Michale / Aldol cascade reaction in the water is reported for the first time, and has the advantages of being relatively wide in substrate range, mild in reaction condition, simple, efficient, environment-friendly, low in cost and the like; the yield reaching up to 93% and the diastereomeric stereoselectivity exceeding 99: 1 can be achieved. The general formulas 1, 5 and 8 are shown in the specification.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to a preparation method of a class of organic compounds. Background technique [0002] Catalyst-free chemical reactions in aqueous solutions have long attracted attention due to the advantages of water as a reaction medium, which is safe, non-toxic, readily available, non-flammable, environmentally friendly, sustainable, and inexpensive. Compared with traditional organic solvents, water also exhibits some unique physical and chemical properties, such as some organic reactions can proceed spontaneously in aqueous solution without catalysts. This kind of reaction not only reduces the pollution to the environment, but also greatly saves the research and development cost of the catalyst. Under the current severe situation of environmental degradation and resource depletion, the development of catalyst-free chemical synthesis in aqueous solution is of great strategic significance. [0003] Tetrah...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/32C07D333/64C07D333/78C07D333/42C07D409/04
CPCC07D333/32C07D333/42C07D333/64C07D333/78C07D409/04
Inventor 胡文冉小琪何延红官智宋健
Owner SOUTHWEST UNIV