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Method for synthesizing 1,4-disubstituted cyclohexene derivative

A synthesis method and technology of cyclohexene, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve problems such as difficult to obtain yield, difficult to obtain single, poor selectivity, etc., to achieve a wide range of applications , strong site selectivity, and the effect of avoiding the use of catalysts

Active Publication Date: 2018-10-02
YUANJIANG HUALONG CATALYST TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Diels Alder addition reaction is a reversible reaction, it is difficult to obtain a higher yield, and there are two additions in the addition reaction, the selectivity is poor, and it is difficult to obtain a purer single one. In addition, the Diels Alder addition reaction Lewis acids are often used as catalysts, and Lewis acids can also promote the polymerization of alkenes, resulting in side reactions

Method used

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  • Method for synthesizing 1,4-disubstituted cyclohexene derivative
  • Method for synthesizing 1,4-disubstituted cyclohexene derivative
  • Method for synthesizing 1,4-disubstituted cyclohexene derivative

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Embodiment Construction

[0042] The following examples are intended to further illustrate the content of the present invention, rather than limit the protection scope of the claims of the present invention.

[0043] All reactions were performed in Schlenk tubes unless otherwise stated.

[0044] All reaction stock solvents were obtained from commercial sources and used without further purification.

[0045] Product separation adopts silica gel chromatographic column, silica gel (particle size 300 mesh-400 mesh).

[0046] 1H NMR (400MHz), 13C NMR (100MHz) and 19F NMR (376MHz) detection adopts Bruker ADVANCEIII spectrometer, with CDCl 3 As the solvent, TMS is used as the internal standard, the chemical shift is in parts per million (ppm), and 0.0 ppm of tetramethylsilane is used as the reference shift. The following abbreviations (or combinations thereof) are used to explain multiplicity: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad. The unit of the coupling constant J...

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Abstract

The invention discloses a method for synthesizing a 1,4-disubstituted cyclohexene derivative. The method comprises the step as follows: an acetophenone compound and an AMS (alpha methyl styrene) compound are subjected to one-pot reaction in a dimethyl sulfoxide solution system containing potassium persulfate, and the cyclohexene derivative is obtained. According to the method, alpha carbon provided by the acetophenone compound, propenyl provided by the AMS and methyl provided by dimethyl sulfoxide constituent a cyclohexene ring altogether for the first time. The synthesis method is implementedwith a one-pot approach, has mild reaction conditions, good selectivity and high yield, requires no additional catalysts, and is beneficial to industrial production.

Description

technical field [0001] The invention relates to a synthesis method of cyclohexene derivatives, in particular to a method for jointly constructing a cyclohexene ring by acetophenone compounds, DMSO and α-methylstyrene compounds, and belongs to the field of organic synthesis. Background technique [0002] Cyclohexene derivatives are based on cyclohexene ring parent, and a series of cyclohexene derivatives are derived by introducing different substituent groups on cyclohexene. The currently reported cyclohexene derivatives are mainly used in medicines and fragrances. Disclosed a kind of cyclohexene compound as Chinese patent (CN106496100A), structural formula is as follows: (wherein, R is selected from: H, M ion, C1-C6 alkyl; R 6 , R 7 , R 8 Independently selected from: H, C1-C4 alkyl, etc.; R 1 Selected from: amino, etc.; R 2 Selected from: H, C1-C4 alkyl, etc.; m selected from: 0,1; R 3 , R 4 Independently selected from: H, C1-C4 alkyl, etc.; n selected from: 1-4; X s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/68C07C49/792C07C49/84C07C49/813C07C49/83C07C49/543C07C319/20C07C323/22C07C253/30C07C255/56C07C255/46C07C67/343C07C69/76C07C201/12C07C205/45C07D307/46
CPCC07C45/68C07C67/343C07C201/12C07C253/30C07C319/20C07D307/46C07C2601/16C07C49/792C07C49/84C07C49/813C07C49/83C07C49/543C07C323/22C07C255/56C07C255/46C07C69/76C07C205/45
Inventor 郭灿城李慧郭欣
Owner YUANJIANG HUALONG CATALYST TECH
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