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Preparation method of E-vinyl sulfones compound

A compound, alkenyl sulfone technology, applied in the field of organic synthetic chemistry, to achieve the effects of wide substrate adaptability, stable process conditions, and high atom economy

Inactive Publication Date: 2017-12-01
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] In view of the deficiencies and defects in the above-mentioned prior art, the technical problem to be solved by the present invention is to research and utilize simple, cheap, stable olefins and thiophenols (mercaptans) to synthesize the method of E-alkenyl sulfone compounds, this new method It is achieved through a non-metallic reagent-mediated approach, avoiding metal contamination, simple, convenient, economical, wide range of substrates and high stereoselectivity

Method used

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  • Preparation method of E-vinyl sulfones compound
  • Preparation method of E-vinyl sulfones compound
  • Preparation method of E-vinyl sulfones compound

Examples

Experimental program
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Effect test

Embodiment 1

[0029]

[0030] At room temperature, add styrene (1.15ml, 10mmol), p-methylthiophenol (2.48g, 20mmol), diiodine pentoxide (4.00g, 12mmol), DBU (1.50ml, 10mmol) into a 50mL reaction flask in sequence and tetrahydrofuran (20 mL). Then, the reaction mixture was stirred at 80° C. for 12 hours (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product E-alkenyl sulfone compound (white solid 2.25 g, yield 87%).

[0031] NMR data: 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.85(d,J=8.3Hz,2H),7.68(d,J=15.5Hz,1H),7.51-7.49(m,2H),7.42-7.41(m,3H), 7.37(d, J=8.1Hz, 2H), 6.87(d, J=15.4Hz, 1H), 2.46(s, 3H); 13 C NMR (CDCl 3 , 125MHz, ppm): δ144.4, 141.9, 137.8, 132.5, 131.1, 130.0, 129.1, 128.5, 127.7, 127.6, 21.6.

Embodiment 2

[0033]

[0034] At room temperature, styrene (1.15ml, 10mmol), thiophenol (2.05ml, 20mmol), diiodine pentoxide (4.00g, 12mmol), DBU (1.50ml, 10mmol) and THF ( 20mL). Then, the reaction mixture was stirred at 80° C. for 12 hours (reaction checked by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product E-alkenyl sulfone compound (yellow solid 2.22 g, yield 91%).

[0035] NMR data: 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.96(d,J=7.4Hz,2H),7.70(d,J=15.4Hz,1H),7.64-7.61(m,1H),7.55(t,J=7.3Hz, 2H), 7.50-7.48(m, 2H), 7.42-7.38(m, 3H), 6.86(d, J=15.4Hz, 1H); 13 C NMR (CDCl 3, 125MHz, ppm): δ142.5, 140.7, 133.4, 132.4, 131.3, 129.4, 129.1, 128.6, 127.7, 127.3.

Embodiment 3

[0037]

[0038] At room temperature, add styrene (1.15ml, 10mmol), 3-methylthiophenol (2.38ml, 20mmol), diiodine pentoxide (4.00g, 12mmol), DBU (1.50ml, 10mmol) into a 50mL reaction flask in sequence ) and tetrahydrofuran (20 mL). Then, the reaction mixture was stirred at 80° C. for 12 hours (reaction checked by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product E-alkenyl sulfone compound (yellow oily liquid 1.88g, yield 73%).

[0039] NMR data: 1 H NMR (CDCl 3 ,500MHz,ppm):δ7.75-7.74(m,2H),7.68(d,J=15.4Hz,1H),7.50-7.48(m,2H),7.44-7.38(m,5H),6.86(d ,J=15.4Hz,1H),2.44(s,3H); 13 C NMR (CDCl 3 , 125MHz, ppm): δ142.3, 140.5, 139.7, 134.2, 132.4, 131.2, 129.2, 129.1, 128.6, 128.0, 127.4, 124.8, 21.4.

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Abstract

The invention discloses a preparation method of an E-vinyl sulfones compound. The preparation method comprises the following steps: dissolving raw materials of olefin and thiophenol (thioalcohol) into a tetrahydrofuran solvent; then adding lodine pentaoxide and organic base DBU (1,8-diazabicyclo undec-7-ene); directly reacting for 12 to 16 hours under 60 to 80 DEG C; separating and purifying a coarse product after stopping reacting, thus obtaining the E-vinyl sulfones compound. The preparation method has the advantages that raw materials are simple and can be easily obtained, the price is cheap, the reaction requires no metal catalyst, metal pollution is avoided, the operation is simple and is free of harsh conditions of water free, oxygen free and the like, the adaptive range of a substrate is wide, the reaction stereoselectivity is high, the process conditions are stable, and a prepared product is easy to purify.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry and relates to a preparation method of E-alkenyl sulfone compound, in particular to a kind of iodine pentoxide and organic base 1,8-diazabicycloundec-7-ene ( DBU)-mediated direct utilization of alkene and thiophenol (thiol) oxidative coupling reaction to synthesize E-alkenyl sulfone compounds. Background technique [0002] E-alkenyl sulfone compounds are an important class of organic structural units, which widely exist in various natural products, drug molecules and pharmaceutical intermediates with anticancer and other activities. E-alkenyl sulfone also exhibits many other good biological activities and is used as a potent inhibitor of enzymatic processes, such as VCAM-1 expression inhibitors, cysteine ​​protease inhibitors, HIV-1 integrase inhibitors, etc. In addition, as an important active intermediate, E-alkenyl sulfone compounds are also widely used in organic synthetic chemistry...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/02C07C317/14C07C317/22C07C317/10C07C317/44C07D213/71C07D213/34
CPCC07C315/02C07D213/34C07D213/71C07C317/14C07C317/22C07C317/10C07C317/44
Inventor 魏伟王雷雷王桦
Owner QUFU NORMAL UNIV
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