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(e)-(2-(phenylsulfonyl)vinyl)benzene and its derivatives and synthesis method

A technology of phenylsulfonyl and benzylsulfonyl, which is applied in the field of synthesis of -vinyl)benzene and its derivatives, achieving the effects of mild reaction conditions, convenient experimental operation, and simple reaction system

Active Publication Date: 2020-10-02
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no synthetic method of (E)-(2-(phenylsulfonyl)vinyl)benzene compounds has been proposed at home and abroad to use (benzylsulfonyl)benzene and paraformaldehyde to directly break bonds and reconnect, and the atom is economical and green. A class of methods for efficiently constructing C-S bonds, currently published in the literature mainly use strong oxidants and transition metal catalysis

Method used

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  • (e)-(2-(phenylsulfonyl)vinyl)benzene and its derivatives and synthesis method
  • (e)-(2-(phenylsulfonyl)vinyl)benzene and its derivatives and synthesis method
  • (e)-(2-(phenylsulfonyl)vinyl)benzene and its derivatives and synthesis method

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Embodiment 1

[0074] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0075] 1 H NMR (400MHz, CDCl 3 )δ7.69(d, J=15.4Hz, 1H), 7.65-7.50(m, 4H), 7.52-7.44(m, 2H), 7.44-7.34(m, 3H), 6.88(d, J=15.5Hz , 1H). 13 C NMR (100MHz, CDCl 3 )δ142.4, 140.5, 133.3, 132.1, 131.1, 129.2, 129.0, 128.5, 127.5, 127.0.

Embodiment 2

[0076] The NMR and mass spectrometry data of embodiment 2 product are as follows:

[0077] 1 H NMR (400MHz, CDCl 3 )δ7.95(d, J=8.0Hz, 2H), 7.69-7.52(m, 4H), 7.38(d, J=7.6Hz, 2H), 7.20(d, J=7.7Hz, 2H), 6.81( d, J=15.4Hz, 1H), 2.37(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ142.6, 141.8, 140.9, 133.2, 129.8, 129.7, 129.3, 128.6, 127.6, 126.0, 21.5.

Embodiment 3

[0078] The NMR and mass spectrum data of embodiment 3 product are as follows:

[0079] 1 H NMR (400MHz, CDCl 3 )δ7.95(d, J=7.4Hz, 2H), 7.65(dd, J=15.3, 8.6Hz, 2H), 7.56(t, J=7.5Hz, 2H), 7.47-7.51(m, 2H), 7.09(t, J=8.5Hz, 2H), 6.80(d, J=15.4Hz, 1H). 13 C NMR (100MHz, CDCl 3 )δ164.3 (d, J=251.5Hz), 141.1, 140.5, 133.4, 130.6 (d, J=87.1Hz), 129.4, 128.5 (d, J=3.3Hz), 127.6, 127.0 (d, J=1.9 Hz), 116.3(d, J=21.9Hz).

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Abstract

The invention relates to a technical scheme that under the joint action of alkaline and N,N-dimethyl formamide, (E)-(2-(phenylsulfonyl)vinyl)benzene and a derivative thereof are efficiently synthesized from multiple components of benzyl compounds and paraformaldehyde in an environment-friendly mode through a one-pot method without transition metal catalysis. Under the promotion effect of Et3N andN,N-dimethyl formamide, vinyl sulfone and a derivative thereof are generated through intermolecular and intramolecular coupling under a mild condition with phenylbenzyl sulfone and paraformaldehyde asraw materials. Transition metal catalysis and a strong oxidant are not required in the method, and a new path is provided for synthesis of vinyl sulfone compounds. The method further has the characteristics that a reaction system is simple, reaction conditions are mild, the quantity of reaction equipment is small, experiment operation is easy and convenient, and the yield is above-average.

Description

technical field [0001] The invention relates to a synthesis method of (E)-(2-(phenylsulfonyl)vinyl)benzene and derivatives thereof, belonging to the field of organic synthesis. Background technique [0002] (E)-(2-(phenylsulfonyl)vinyl)benzene and its derivatives are important organic compounds for activity-based protein profiling (ABPP) probes and covalent protease inhibitors, and vinyl sulfone is very Valuable synthetic target molecular skeletons are also important components in natural products and drug discovery, because they are widely used in drug synthesis, and have extremely high application value in fields such as agriculture and materials. So far, no synthetic method of (E)-(2-(phenylsulfonyl)vinyl)benzene compounds has been proposed at home and abroad to use (benzylsulfonyl)benzene and paraformaldehyde to directly break bonds and reconnect, and the atom is economical and green. A class of methods for efficiently constructing C-S bonds, currently published in the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C317/14C07C315/04C07C317/44C07C317/18C07C317/10C07D215/12
Inventor 肖福红胡杨凌邓国军黄华文
Owner XIANGTAN UNIV
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