Method for continuously and electrically synthesizing spiro[4.5]trienone by using micro-reaction device

A technology for electrosynthesis and trienone, applied in electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problems of difficulty in realizing industrial scale-up, hidden dangers in safety and environment, harsh reaction conditions, etc., and achieves easy operation and safe reaction process. , the effect of mild reaction conditions

Active Publication Date: 2020-06-05
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above methods have been reported, there are still some obvious disadvantages in these methods: the reaction conditions are harsh, oxidants and bases are required, and expensive metal catalysts are required
These defects not only bring safety and environmental hazards, but also make it difficult to achieve industrial scale-up

Method used

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  • Method for continuously and electrically synthesizing spiro[4.5]trienone by using micro-reaction device
  • Method for continuously and electrically synthesizing spiro[4.5]trienone by using micro-reaction device
  • Method for continuously and electrically synthesizing spiro[4.5]trienone by using micro-reaction device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The synthesis of embodiment 1 compound 3a:

[0045] Dissolve 0.5mmol (0.126g) of compound 1a, 0.5mmol (0.156g) of diphenyldiselenide 2a and 1mmol of tetrabutylammonium hexafluorophosphate (0.387g) in acetonitrile / hexafluoroisopropanol (10mL, volume ratio 3 / 1, the same below), to obtain a homogeneous solution A, add in the syringe pump a; the injection flow rate of the syringe pump a is 225 μL / min; the applied current is 15mA; the microchannel reactor reaction volume V=225 μL, the reaction The time was 1 min; after one period of reaction in the microchannel reactor, the reaction liquid was collected, and the product yield was calculated by HPLC method to be 73%, and the product 3a was obtained after separation by column chromatography. 1H NMR (400MHz, Chloroform-d) δ7.36–7.31(m,2H),7.28–7.23(m,1H),7.20–7.13(m,3H),7.08(dd,J=8.0,6.6Hz,4H ),6.60–6.54(m,2H),6.30–6.25(m,2H). 13 C NMR(101MHz,Chloroform-d)δ182.73,168.65,161.65,141.54,133.25,130.78, 129.40,128.69,128.24,127.52...

Embodiment 2

[0046] The synthesis of embodiment 2 compound 3a:

[0047] 0.5mmol (0.126g) of compound 1a, 0.5mmol (0.156g) of diphenyldiselenide 2a and 1mmol of tetrabutylammonium tetrafluoroborate (0.329g) were dissolved in acetonitrile / hexafluoroisopropanol (10mL, 3 / In 1), obtain homogeneous solution A, add in the syringe pump a; The injection flow rate of syringe pump a is 225 μ L / min; Applied electric current is 15 mA; Microchannel reactor reaction volume V=225 μ L, reaction time 1min; After one period of reaction in the reactor, the reaction liquid was collected, and the product yield was calculated by HPLC method to be 70%, and the product 3a was obtained after separation by column chromatography.

Embodiment 3

[0048] The synthesis of embodiment 3 compound 3a:

[0049] 0.5mmol (0.126g) of compound 1a, 0.5mmol (0.156g) of diphenyldiselenide 2a and 1mmol of tetraethylammonium perchlorate (0.229g) were dissolved in acetonitrile / hexafluoroisopropanol (10mL, 3 / In 1), obtain homogeneous solution A, add in the syringe pump a; The injection flow rate of syringe pump a is 225 μ L / min; Applied electric current is 15 mA; Microchannel reactor reaction volume V=225 μ L, reaction time 1min; After one period of reaction in the reactor, the reaction liquid was collected, and the product yield calculated by HPLC was 69%, and the product 3a was obtained after separation by column chromatography.

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Abstract

The invention discloses a method for continuously and electrically synthesizing spiro[4.5]trienone by using a micro-reaction device. According to the method, an alkynyl compound and diselenide are taken as reaction raw materials, a graphite plate is taken as an anode and a platinum sheet is taken as a cathode, a continuous electrolytic reaction is carried out in a micro-channel reaction device inthe presence of an electrolyte and a solvent, and the spiro[4.5]trienone is obtained through a free radical cascade reaction and dearomatization. The invention provides the novel preparation method ofthe spiro[4.5]trienone, and the preparation method is green, safe and efficient in technological operation and mild in reaction condition.

Description

technical field [0001] The invention belongs to the field of organic electrosynthesis, and in particular relates to a method for continuously electrosynthesizing spiro[4.5]trienone by using a micro-reaction device. Background technique [0002] Spirocycles are a class of key structural motifs frequently found in many natural products, pharmacologically active compounds and materials. Among various spiro compounds, spiro[4,5]trienones have attracted intense interest due to their excellent biological activities and diverse synthetic applications in the preparation of complex molecular frameworks. Dearomatization reactions provide the most efficient method for the synthesis of spiro or fused carbocycles from readily available compounds. [0003] At present, the method for constructing spiro[4,5]trienone compound skeleton includes: (1) carrying out dearomatization spirocyclization reaction by electrophilic halogenating reagent, see reference (J.Am.Chem.Soc.2005, 127,12230-1223...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 杨照朱家靖方正王志祥
Owner CHINA PHARM UNIV
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