Method for synthesizing 3-indole selenide alcohol organic compound

A technology for organic compounds and synthesis methods, applied in the field of organic compound synthesis, can solve the problems of metal catalysts that do not conform to environmental protection, unpleasant odor, etc., and achieves the effects of high atom utilization, efficient reaction, and simple post-processing

Active Publication Date: 2018-05-18
温州大学苍南研究院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires transition metal catalysis and diselenide as a raw material, and the unpleasant stench and the use of metal catalysts do not meet the requirements of environmental protection.

Method used

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  • Method for synthesizing 3-indole selenide alcohol organic compound
  • Method for synthesizing 3-indole selenide alcohol organic compound
  • Method for synthesizing 3-indole selenide alcohol organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of 2-(3-indoleselenyl)-1-cyclohexyl alcohol:

[0025]

[0026] At room temperature, add a stir bar, selenium powder (0.8mmol), lithium tert-butoxide (1.2mmol), phase transfer catalyst tetrabutylammonium iodide (0.8mmol), indole (0.4mmol) into a 25mL Schlenk tube, and then Vacuumize, fill with nitrogen, back and forth vacuum-fill nitrogen three times, add cyclohexene oxide (0.8mmol) and deionized water (2mL) under the protection of nitrogen, then stir at room temperature for 5min, and finally move to 45°C for heating React in the tank, use TLC (or GC-MS) tracking detection during the reaction, after detection, the reaction is complete after 12 hours.

[0027] After the reaction is completed and the reaction mixture is cooled, the reaction mixture is first diluted with 15 mL of water, then extracted three times with 45 mL of ethyl acetate, and the organic phase is collected three times, then dried with anhydrous sodium sulfate, filtered, concentrated under re...

Embodiment 2

[0034] Synthesis of 2-(5-fluoro-3-indoleselenyl)-1-cyclohexyl alcohol:

[0035]

[0036] At room temperature, add a stir bar, selenium powder (0.8mmol), lithium tert-butoxide (1.2mmol), tetrabutylammonium iodide (0.8mmol), 5-fluoro-indole (0.4mmol) into a 25mL Schlenk tube, Then vacuumize, fill with nitrogen, back and forth vacuumize-fill nitrogen three times, add cyclohexene oxide (0.8mmol) and deionized water (2mL) under the protection of nitrogen, then stir at room temperature for 5min, and finally move to 45°C React in the heating tank, use TLC (or GC-MS) tracking detection during the reaction, after detection, the reaction is complete after 12 hours.

[0037] After the reaction is completed and the reaction mixture is cooled, the reaction mixture is first diluted with 15 mL of water, then extracted three times with 45 mL of ethyl acetate, and the organic phase is collected three times, then dried with anhydrous sodium sulfate, filtered, concentrated under reduced press...

Embodiment 3

[0044] Synthesis of 2-(6-chloro-3-indoleselenyl)-1-cyclohexyl alcohol:

[0045]

[0046]At room temperature, add a stir bar, selenium powder (0.8mmol), lithium tert-butoxide (1.2mmol), tetrabutylammonium iodide (0.8mmol), 6-chloro-indole (0.4mmol) into a 25mL Schlenk tube, Then vacuumize, fill with nitrogen, back and forth vacuumize-fill nitrogen three times, add cyclohexene oxide (0.8mmol) and deionized water (2mL) under the protection of nitrogen, then stir at room temperature for 5min, and finally move to 45°C React in the heating tank, use TLC (or GC-MS) tracking detection during the reaction, after detection, the reaction is complete after 12 hours.

[0047] After the reaction is completed and the reaction mixture is cooled, the reaction mixture is first diluted with 15 mL of water, then extracted three times with 45 mL of ethyl acetate, and the organic phase is collected three times, then dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressu...

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Abstract

The invention discloses a method for synthesizing a 3-indole selenide alcohol organic compound. The method is characterized by comprising the following steps: taking an indole compound and cyclohexeneoxide / cyclopentene oxide / 1,2-epoxybutane / isobutylene oxide / 3,3-dimethyl epoxybutane / 2-furfuryl glycidyl ether as reaction substrates, taking elemental selenium as a selenium source, taking water or an organic solvent as a reaction solvent, adding a phase transfer catalyst tetrabutylammonium iodide into the water when the water serves as the reaction solvent, and performing transition-metal-free catalysis in a nitrogen atmosphere in the presence of an inorganic base, thereby obtaining the 3-indole selenide alcohol organic compound. The method disclosed by the invention has the beneficial effects that the 3-indole selenide alcohol organic compound can be synthesized at high yield and high purity by adopting the method disclosed by the invention, and the method is mild in reaction conditions, wide in reaction substrate range, excellent in functional group tolerance, simple in after-treatment, simple and convenient to operate and suitable for large-scale industrialized production and provides a brand new synthetic route for high-efficiency and rapid synthesis of the compounds.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 3-indoleselenoalcohol organic compounds, and belongs to the technical field of organic compound synthesis. Background technique [0002] 3-Indoleselenoalcohol organic compounds are a class of asymmetric selenoether compounds in selenium-containing compounds, which have good physiological activities. The development of selenium-containing compounds through new chemical structures is a new green synthetic method for the synthesis of 3- Indole selenoalcohols are of great significance in organic synthesis and medicinal chemistry. [0003] In 2003, Venkataraman et al. reported a CuI / 2,9-dimethyl-1,10-phenanthroline catalytic system to catalyze the preparation of asymmetric diaryl monoselenides from aryl iodide and phenylselenol. This method adopts different bases according to the electronic effect on the aryl iodide: when the substituent on the ...

Claims

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Application Information

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IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 刘妙昌徐雨婷李鸿辰闵林高超高文霞黄小波吴华悦李国兴吴祥庭
Owner 温州大学苍南研究院
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