A method for constructing cyclohexene derivatives from arylethanone, 2-arylpropene and dimethyl sulfoxide
A technology of dimethyl sulfoxide and aryl ethyl ketone, applied in the field of synthesis of cyclohexene derivatives, can solve the problems of difficult to obtain yield, difficult to obtain single, poor selectivity, etc., and achieves wide adaptability and site selectivity. Strong, avoid the effect of the use of catalysts
Active Publication Date: 2021-01-12
YUANJIANG HUALONG CATALYST TECH
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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
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[0040] 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.
[0041] All reactions were performed in Schlenk tubes unless otherwise stated.
[0042] All reaction stock solvents were obtained from commercial sources and used without further purification.
[0043] Product separation adopts silica gel chromatographic column, silica gel (particle size 300 mesh-400 mesh).
[0044] 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 constructing a cyclohexene derivative through substitutional acetophenone, 2-aryl propylene and dimethyl sulfoxide. According to the method, the substitutional acetophenone and the 2-aryl propylene are subjected to one-pot reaction in a dimethyl sulfoxide solution system containing potassium persulfate and / or sodium persulfate, so that the cyclohexene derivative is obtained. According to the method, for the first time, a cyclohexene ring is constructed through the substitutional acetophenone which provides alpha carbon, the 2-aryl propylene which provides propenyl and the dimethyl sulfoxide which provides methyl, the synthesis method is implemented through a one-pot method, moreover, reaction conditions are mild, no additional catalysts are needed, theselectivity is good, the yield is high, and the synthesis method is beneficial for industrial production.
Description
technical field [0001] The invention relates to a method for synthesizing cyclohexene derivatives, in particular to a method for jointly constructing cyclohexene by aryl ethyl ketone, DMSO and 2-aryl propylene, which 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 selected from: C...
Claims
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IPC IPC(8): C07C45/68C07C67/343C07C201/12C07C319/14C07D213/50C07D307/46C07D319/06C07D333/22C07D405/06C07D407/04C07D409/06C07C49/792C07C49/794C07C323/22C07C321/10C07C49/84C07C49/813C07C69/76C07C205/45C07C49/83
CPCC07B2200/05C07C45/68C07C67/343C07C201/12C07C319/14C07D213/50C07D307/46C07D319/06C07D333/22C07D405/06C07D407/04C07D409/06C07C2601/16C07C49/792C07C49/794C07C323/22C07C321/10C07C49/84C07C49/813C07C69/76C07C205/45C07C49/83
Inventor 郭灿城李慧郭欣
Owner YUANJIANG HUALONG CATALYST TECH