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Synthetic method of 1,3-dithiane structure-containing polysubstituted olefin derivatives

A dithiane, multi-substitution technology, applied in the field of synthesis of multi-substituted olefin derivatives

Inactive Publication Date: 2016-01-27
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, the lithiated 1,3-dithiane molecules can directly undergo carbon lithiation reaction with olefinic compounds, which can realize the construction of carbon-carbon bonds, but for the preparation of multi-substituted olefins containing 1,3-dithiane structure pose a challenge

Method used

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  • Synthetic method of 1,3-dithiane structure-containing polysubstituted olefin derivatives
  • Synthetic method of 1,3-dithiane structure-containing polysubstituted olefin derivatives
  • Synthetic method of 1,3-dithiane structure-containing polysubstituted olefin derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 In a 50 milliliter round bottom flask, add 1,3-dithiane (1mmol), add N-chlorosuccinimide (1.2mmol) after dissolving with 10 milliliters of 1,2-dichloroethane , reacted for 40 to 60 minutes, then added 1,1-stilbene (0.9 mmol) and boron trifluoride ether (or anhydrous ferric chloride, methanesulfonic acid) (0.1 mmol), and reacted at room temperature for 10 to 12 Hour. After TLC monitoring, the reaction was stopped after the reaction was complete, and the product was obtained by column chromatography after evaporating the solvent.

Embodiment 2

[0022] Example 2 In a 50 milliliter round bottom flask, add 1,3-dithiane (1mmol), add N-chlorosuccinimide (1.2mmol) after dissolving with 10 milliliters of 1,2-dichloroethane , reacted for 40 to 60 minutes, then added 1,1-bis(4-methylphenyl)-propene (0.9mmol) and boron trifluoride-free ether (or anhydrous ferric chloride, methanesulfonic acid) (0.1 mmol), react at room temperature for 10-12 hours. After TLC monitoring, the reaction was stopped after the reaction was complete, and the product was obtained by column chromatography after evaporating the solvent.

Embodiment 3

[0023] Example 3 In a 50 milliliter round bottom flask, add 1,3-dithiane (1mmol), add N-chlorosuccinimide (1.2mmol) after dissolving with 10 milliliters of 1,2-dichloroethane , reacted for 40 to 60 minutes, then added 1-phenyl-1-(4-chlorophenyl)-ethylene (0.9mmol) and boron trifluoride ether (or anhydrous ferric chloride, methanesulfonic acid) (0.1 mmol), react at room temperature for 10-12 hours. After TLC monitoring, the reaction was stopped after the reaction was complete, and the product was obtained by column chromatography after evaporating the solvent.

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Abstract

The invention relates to a synthetic method of 1,3-dithiane structure-containing polysubstituted olefin derivatives. The method comprises the following steps: carrying out an oxyradical coupling reaction on 1,3-dithiane and polysubstituted olefins in a solvent in the presence of a catalyst Lewis acid and an activator N-chlorosuccimide with air or oxygen as an oxidant, separating, and purifying to obtain the 1,3-dithiane structure-containing polysubstituted olefin derivatives. The method has the advantages of avoiding of use of a metal catalyst due to cheap and easily available substrates used in the invention, environmental protection, simple reaction process and mild conditions, the 1,3-dithiane structure-containing polysubstituted olefin derivatives have good function group tolerance and can be directly obtained through a one-kettle process, the method has beneficial technical effects, and can be well applied in scientific researches and industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing multi-substituted olefin derivatives containing 1,3-dithiane structure Background technique [0002] 1,3-dithiane was applied to organic synthesis by Corey and Seebach in 1965. With the in-depth study of chemical research, especially the work of the A.B.SmithIII group of the University of Pennsylvania, the organic synthesis reactions involving 1,3-dithiane are increasing, and the research in this area has aroused the great interest of many synthetic chemists , it has been widely used in the construction of carbon-carbon bonds and key intermediates. Usually, in the reaction of building carbon-carbon bonds, 1,3-dithiane molecules form nucleophiles under the action of strong bases to react with various electrophiles. -BuLi in THF or Et 2 Low temperature deprotonation in O; for the deprotonation of substituted thiane molecules, sometimes a stronger base such as t-BuLi is needed, and it needs to be assis...

Claims

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Application Information

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IPC IPC(8): C07D339/08
Inventor 唐寿初杜文斌田丽霞赖俊汕
Owner LANZHOU UNIVERSITY
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