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Thiooxacycloalkane compound and synthetic method therefor

A technology for thiooxane and oxane, which is applied in the field of thiooxane compounds and their synthesis, and achieves the effects of easy availability, environmental friendliness and low toxicity of raw materials

Active Publication Date: 2015-12-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And utilize enol and substituted or unsubstituted sodium benzene sulfinate as raw material, under the effect of copper salt, the method that one-step synthesis of thiooxetane is not reported yet.

Method used

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  • Thiooxacycloalkane compound and synthetic method therefor
  • Thiooxacycloalkane compound and synthetic method therefor
  • Thiooxacycloalkane compound and synthetic method therefor

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Add 0.25 mmol of 4-penten-1-ol, 0.25 mmol of sodium p-toluenesulfinate, 0.025 mmol of cuprous chloride, and 2 ml of acetonitrile into a screw-top test tube, and stir and react at 80°C for 5 hours , stop heating and stirring, and cool to room temperature. The reaction material was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain a thioxacycloalkane compound. The column chromatography eluent used was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 3:1 , yield 85%.

Embodiment 2

[0040] Add 0.25 mmol of 4-penten-1-ol, 0.30 mmol of sodium p-toluenesulfinate, 0.025 mmol of cuprous chloride, and 2 ml of acetonitrile into a screw-top test tube, and stir and react at 90°C for 30 hours , stop heating and stirring, and cool to room temperature. The reaction material is decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain a thioxacycloalkane compound. The column chromatography eluent used is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 1:1 , yield 81%.

Embodiment 3

[0042] Add 0.25 mmol of 4-penten-1-ol, 0.40 mmol of sodium p-toluenesulfinate, 0.020 mmol of cuprous chloride, and 2 ml of toluene into a screw-top test tube, and stir and react at 80°C for 6 hours , stop heating and stirring, and cool to room temperature. The reaction material was decompressed and rotary evaporated to remove the solvent, and then separated and purified by column chromatography to obtain a thioxacycloalkane compound. The column chromatography eluent used was a mixed solvent of petroleum ether: ethyl acetate with a volume ratio of 5:1 , yield 80%.

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Abstract

The invention belongs to the technical field of organic synthesis and discloses a thiooxacycloalkane compound and a synthetic method therefor. The synthetic method comprises the following steps: adding enol, substituted or unsubstituted sodium benzenesulfinate and a solvent into a reactor; adding copper salt as a catalyst, and carrying out a stirring reaction for 3-48 hours at 50-150 DEG C; after reaction, cooling the reactor to room temperature; evaporating the solvent at a reduced pressure to obtain a coarse product; and purifying the coarse product through column chromatography to obtain the thiooxacycloalkane compound. The synthetic method provided by the invention is safe and simple to operate, the raw materials are low in price and are easily available, and the method is good in adaptability to functional group, wide in substrate adaptability and environmental-friendly, so that industrial production is facilitated, and the method is widely applied to synthesis of pesticides, medicines and natural products.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a thioxeterocycloalkane compound and a synthesis method thereof. Background technique [0002] With the continuous development of social economy, the problem of globalized energy consumption and environmental pollution are becoming more and more serious. In chemical research, achieving sustainable development has become an important theme. How to develop environmentally friendly new green synthesis methods to achieve efficient use of resources is one of the main directions of organic chemistry progress. [0003] Oxycycloalkane compounds are a class of compounds with biological activity and drugs, which are widely used in many aspects such as biochemical industry, medicine, materials, daily chemicals, etc., especially in drugs such as antimicrobial and antitumor cells. Pharmacological activity (Chen Yong, Li Xiang, Chen Jianwei, et al. Anti-tumor effect of d...

Claims

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Application Information

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IPC IPC(8): C07D307/10C07D305/06C07D309/04C07D313/04
CPCC07D305/06C07D307/10C07D309/04C07D313/04
Inventor 江焕峰高颖兰高杨伍婉卿
Owner SOUTH CHINA UNIV OF TECH
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