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Cyanoalkoxy substituted tetra-substituted olefin derivatives and synthesis thereof

A cyanoalkoxy, tetra-substituted technology, applied in the field of chemical organic synthesis, to achieve the effects of mild conditions, wide applicability and high efficiency

Active Publication Date: 2020-10-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And, take cyclobutanone oxime ester as raw material, the method for synthesizing four substituted olefins substituted with cyanoalkoxy groups has not been reported yet

Method used

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  • Cyanoalkoxy substituted tetra-substituted olefin derivatives and synthesis thereof
  • Cyanoalkoxy substituted tetra-substituted olefin derivatives and synthesis thereof
  • Cyanoalkoxy substituted tetra-substituted olefin derivatives and synthesis thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] In a 25mL schlenk tube, add 3,3-dialkylthio-2-propene-1-one compound 2a (0.3mmol), cyclobutanone oxime ester 3a (0.6mmol), copper chloride (10mol%) under oxygen. ) And 3.0 mL trifluorotoluene, stirring at 100°C for 5 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=50:1) to obtain the target product 1a (46.5mg, yield 50%). The target product was confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. In this reaction, oxygen was used as both the reaction gas and the oxidant.

[0035] Compound characterization data

[0036] Cyanoalkoxy substituted tetra-substituted olefin derivative (1a), yellow liquid. 1 H NMR(400MHz, CDCl 3 )δ7.91(m,2H,aromatic CH),7.59(t,J=7.4Hz,1H,aromatic CH),7.49(t,J=7.6Hz,2H,aromatic CH),3.89(t,J=5.6 Hz, 2H, OCH 2 ), 2.57(t,J=7.2Hz,2H,CH 2 CN), ...

Embodiment 2

[0038]

[0039] In a 25mL schlenk tube, add 3,3-dialkylthio-2-propene-1-one compound 2a (0.3mmol), cyclobutanone oxime ester 3a (0.6mmol), copper chloride (10mol%) under nitrogen. ), hydrogen peroxide (0.6mmol) and 3.0mL trifluorotoluene, stirring at 100°C for 5 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent: petroleum ether (60-90°C) / ethyl acetate, v / v=50:1) to obtain the target product 1a (37.0mg, yield 40%). The target product was confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The characterization data of compound 1a is shown in Example 1.

Embodiment 3

[0041]

[0042] In a 25mL schlenk tube, add 3,3-dialkylthio-2-propene-1-one compound 2b (0.3mmol), cyclobutanone oxime ester 3a (0.6mmol), copper chloride (10mol%) under oxygen. ) And 3.0 mL trifluorotoluene, stirring at 100°C for 5 hours. After cooling to room temperature, the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=50:1) to obtain the target product 1b (44mg, yield 43%). The target product was confirmed by nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry.

[0043] Compound characterization data

[0044] Cyanoalkoxy substituted tetra-substituted olefin derivative (1b), yellow liquid. 1 H NMR(400MHz, CDCl 3 )δ7.92(m,2H,aromatic CH), 7.59(t,J=7.4Hz,1H,aromatic CH), 7.48(t,J=7.6Hz,2H,aromatic CH), 3.87(t,J=5.6 Hz, 2H, OCH 2 ), 2.88(q,J=7.3Hz,2H,SCH 2 ),2.58(m,4H,SCH 2 and CH 2 CN),1.95(m,2H,OCH 2 CH 2 ),1.31(t,J=7.3Hz,3H,CH 2...

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Abstract

The invention discloses a method for synthesizing cyanoalkoxy substituted tetra-substituted olefin derivatives with potential biological activity. According to the method, 3,3-dialkylthio-2-propylene-1-ketone and cyclobutanone oxime ester, which are easy to prepare and have structural diversity and multiple reaction centers, are used as raw materials, so that the free radicals are generated through cyclobutanone oxime ester to carry out olefin addition, and the cyanoalkoxy substituted tetra-substituted olefin derivative is generated in one step. The method has the advantages of easily available raw materials, simple operation, mild synthesis reaction conditions, high reaction efficiency, and diversity of functional groups.

Description

Technical field [0001] The invention belongs to the field of chemical organic synthesis, and in particular relates to a method for synthesizing a cyanoalkoxy substituted tetra-substituted olefin derivative with potential biological activity. Background technique [0002] Multi-substituted olefins are important structural units in organic functional materials, drug molecules, and natural products. They are the core framework of many natural products and physiologically active compounds. They are also important organic synthesis intermediates. Recent studies have shown that cyanoalkoxy substituted compounds have good applications in medicinal chemistry and enzyme chemistry (J.Med.Chem.2010,53,7902-7917; ACS Med.Chem.Lett.2014,5,937 -941; Catal.Sci.Technol.2014,4,2871-2876). [0003] At present, the method of synthesizing polysubstituted olefins is mainly through the synthesis of carbon-carbon bonds catalyzed or promoted by different transition metals. However, these methods basical...

Claims

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Application Information

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IPC IPC(8): C07C321/18C07C319/20C07D231/18
CPCC07C321/18C07D231/18
Inventor 娄江余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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