A kind of cyclohexene derivative and its synthesis method

A synthesis method and derivative technology, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve problems such as difficult to obtain single, poor selectivity, side reactions, etc.

Active Publication Date: 2021-01-12
YUANJIANG HUALONG CATALYST TECH
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  • Summary
  • 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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  • A kind of cyclohexene derivative and its synthesis method
  • A kind of cyclohexene derivative and its synthesis method
  • A kind of cyclohexene derivative and its synthesis method

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Embodiment Construction

[0060]The following examples are intended to further illustrate the content of the present invention, but not to limit the protection scope of the claims of the present invention.

[0061]Unless otherwise stated, all reactions were performed in Schlenk tubes.

[0062]All reaction starting solvents were obtained from commercial sources and used without further purification.

[0063]The product is separated using silica gel chromatographic column, silica gel (particle size 300-400 mesh).

[0064]1H NMR (400MHz), 13C NMR (100MHz) and 19F NMR (376MHz) are detected by Bruker ADVANCEIII spectrometer, with CDCl3As a solvent, TMS as an internal standard, chemical shifts in parts per million (ppm), and 0.0 ppm of tetramethylsilane as a reference shift. The following abbreviations (or combinations thereof) are used to explain the multiplicity: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad peak. The unit of the coupling constant J is hertz (Hz). The chemical shift is expres...

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Abstract

The invention discloses a cyclohexene derivative and a preparation method thereof. According to the method, ketone compounds and 2-aryl propene are subjected to a one-pot reaction in a dimethyl sulfoxide solution system containing persulfate, and the cyclohexene derivative is obtained. According to the method, the ketone compounds provide alpha-carbon, 2-aryl propene provides propenyl and dimethylsulfoxide provides methyl for the first time for joint construction of a cyclohexene ring. The synthesis method is implemented with a one-pot method, the reaction conditions are mild, no additional catalyst is required, the selectivity is good, the yield is high and industrial production is facilitated.

Description

Technical field[0001]The invention relates to a cyclohexene derivative and a synthesis method thereof, in particular to a method for jointly constructing a cyclohexene ring from a ketone compound, DMSO and 2-arylpropene, and belongs to the field of organic synthesis.Background technique[0002]Cyclohexene derivatives are based on the cyclohexene ring parent, and a series of cyclohexene derivatives are derived by introducing different substituent groups on cyclohexene. The cyclohexene derivatives reported so far are mainly used in medicine and perfume. For example, a Chinese patent (CN106496100A) discloses a cyclohexene compound, the structural formula is as follows:(Wherein R is selected from: H, M ion, C1-C6 alkyl; R6, R7, R8Independently selected from: H, C1-C4 alkyl, etc.; R1Selected from: amino, etc.; R2Selected from: H, C1-C4 alkyl, etc.; m is selected from: 0, 1; R3, R4Independently selected from: H, C1-C4 alkyl, etc.; n is selected from: 1 to 4; X is selected from: CH2, O, S, e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/68C07C49/792C07C49/84C07C49/813C07C49/83C07C49/563C07C49/543C07C319/20C07C323/22C07C253/30C07C255/56C07C255/46C07C67/343C07C69/76C07C201/12C07C205/45C07D307/46C07D333/22C07D213/50
CPCC07C45/68C07C67/343C07C201/12C07C253/30C07C319/20C07D213/50C07D307/46C07D333/22C07C2601/16C07C49/792C07C49/84C07C49/813C07C49/83C07C49/563C07C49/543C07C323/22C07C255/56C07C255/46C07C69/76C07C205/45
Inventor 郭灿城李慧郭欣
Owner YUANJIANG HUALONG CATALYST TECH
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