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(E)-alkenyl sulfone compound and preparation method thereof

A compound, alkenyl sulfone technology, applied in the field of alkenyl sulfone compounds and their preparation, can solve the problems of poor regioselectivity and stereoselectivity, cumbersome production, and many steps, and achieve high yield, good substrate compatibility, Simple operation effect

Inactive Publication Date: 2017-09-15
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] With the application of sulfene more and more widely, people have gradually found some methods of synthesizing sulfone compounds, but there are also disadvantages such as the use of toxic or unstable substances, many and cumbersome steps, and the production of a large amount of chemical waste
What's more, many methods have poor regio- and stereoselectivity, resulting in mixtures of Z / E-type sulfones

Method used

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  • (E)-alkenyl sulfone compound and preparation method thereof
  • (E)-alkenyl sulfone compound and preparation method thereof
  • (E)-alkenyl sulfone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Transition metal copper catalyzed synthesis of alkenyl sulfone from phenylpropiolic acid and phenylsulfonyl hydrazide with respect to catalyst, solvent and reaction time. Where [Cu] is the copper catalyst, S is the organic solvent, and T is the reaction temperature. After screening the reaction conditions, we got the optimal reaction conditions, THF was the solvent, Cu 2 O is the catalyst, the temperature is 80°C, the reaction time is 24h, and oxygen in the air is used as the oxidant.

[0029]

[0030]

[0031]

[0032] in a for 1 H NMR yield, 18 b For the reaction gas to N 2 gas.

Embodiment 2

[0034] Copper-catalyzed synthesis of alkenyl sulfones from phenylpropiolic acid series substrates and phenylsulfonyl hydrazides. Through the extended research on phenylpropiolic acid substrates, it is found that phenylpropiolic acid with different substituent groups can be applied to this method and obtain moderate to good yields.

[0035]

[0036] The specific experimental operation is to add phenylpropiolic acid substrate (0.02mmol), phenylsulfonyl hydrazide (0.04mmol) and THF (2.0mL) in sequence in a dry and clean reaction tube. React in 24h. After the reaction, the organic phase was extracted, and after the solvent was removed under reduced pressure, the target product 3 was obtained by thin-layer chromatography, as follows:

[0037] Target product 3ba: (E)-1-methyl-4-(2-(phenylsulfonyl)vinyl)benzene

[0038]

[0039] 1 H NMR (400MHz, CDCl 3 )δ7.94(d, J=8.0Hz, 2H), 7.66(d, J=15.4Hz, 1H), 7.63-7.51(m, 3H), 7.38(d, J=8.0Hz, 2H), 7.19( d,J=8.0Hz,2H),6.80(d,J=15.4Hz...

Embodiment 3

[0067] Copper-catalyzed synthesis of alkenyl sulfones from phenylpropiolic acid and phenylsulfonyl hydrazide series substrates. Through the extended research on phenylsulfonyl hydrazide substrates, it is found that the method is suitable for phenyl sulfonyl hydrazides substituted by electron-withdrawing groups or electron-deficient groups, as well as phenyl sulfonyl hydrazides with large steric hindrance effect. , and good yields can also be obtained.

[0068]

[0069] The specific experimental operation is to add phenylpropiolic acid (0.02mmol), phenylsulfonyl hydrazide series substrates (0.04mmol) and THF (2.0mL) in sequence in a dry and clean reaction tube. React in 24h. After the reaction, the organic phase was extracted, and after the solvent was removed under reduced pressure, the target product 3 was obtained by thin-layer chromatography, as follows:

[0070] Target product 3aa: (E)-1-Phenylsulfonyl-2-phenylethene

[0071]

[0072] 1 H NMR (400MHz, CDCl 3 )δ7...

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Abstract

The present invention relates to a (E)-alkenyl sulfone compound and a preparation method thereof. The preparation method comprises: dissolving a benzenesulfonyl hydrazide-based substrate and a phenylpropiolic acid substrate in an organic solvent, adding a copper catalyst, and carrying out a reaction by using oxygen in air as an oxidizing agent so as to obtain the (E)-alkenyl sulfone compound, wherein the chemical formula is defined in the specification. Compared to the method in the prior art, the method of the present invention has the following characteristics that the finally required (E)-alkenyl sulfone compound can be obtained with the inexpensive catalyst Cu2O and the green oxidant O2 without the additional additives, and the method provides good compatibility for the substrates having different electronic effects and steric hindrance on the aromatic ring, and has high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an (E)-alkenyl sulfone compound and a preparation method thereof. Background technique [0002] Alkenyl sulfone compounds play a huge role in the biological activity of medicine and are a class of organic compounds of great value. For example, substituted sulfones are potent small-molecule inhibitors of many enzymes, such as HIV-1 integrase and cysteine ​​protease, and are frequently used in the drug design process in the pharmaceutical industry. At the same time, this type of compound is also an important skeleton in organic synthesis. Due to the electron-withdrawing ability of sulfone in sulfone, it can be used as a Michael acceptor and can also be used in cycloaddition reactions. (a) Wang G., Mahesh U., Chen G.Y.J., Yao S.-Q., Organic Letters, 2003, Vol.5:737~740; (b) Gordon C.P., Griffith R., Keller P.A., Medicinal Chemistry, 2007, Vol.3:199~220; (c) Carr R.V.C., Paquette L...

Claims

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Application Information

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IPC IPC(8): C07C317/14C07C317/22C07C317/24C07C315/04
CPCC07C317/14C07B2200/09C07C315/04C07C317/22C07C317/24
Inventor 张扬会陆爱兰潘树雷
Owner TONGJI UNIV
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