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Preparation method of beta-carbonyl sulfone compound

A technology of compound and carbonyl sulfone, which is applied in the field of preparation of β-carbonyl sulfone compounds, can solve the problems of narrow substrate range, large structure restriction of compound A, cumbersome operation, etc., and achieve product purification, easy product and stable process conditions Effect

Active Publication Date: 2020-11-24
SOUTHWEST MEDICAL UNIVERISTY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The oxidizing agent used in this method is a peroxide, and the operation is loaded down with trivial details (such as: the catalyst is added in three times and needs to be treated with a cation-exchange membrane before column chromatography), and the structure restriction of compound A is relatively large, resulting in a narrow range of substrates

Method used

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  • Preparation method of beta-carbonyl sulfone compound
  • Preparation method of beta-carbonyl sulfone compound
  • Preparation method of beta-carbonyl sulfone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: 2-p-toluenesulfonylacetophenone

[0040]

[0041] 2,3-diphenyl-1-propene (97 mg, 0.5 mmol), p-toluenesulfonyl hydrazide (186 mg, 1.0 mmol), copper triflate (9 mg, 0.025 mmol) and acetonitrile / water (V : V=9:1, 2mL) into the reaction tube (25mL), the reaction tube was quickly evacuated, covered with an oxygen balloon, and reacted at 65°C for 12 hours. After the reaction, the solvent was removed under reduced pressure, and the product (white solid, yield 93%) was separated by column chromatography (100-200 mesh, petroleum ether: ethyl acetate = 8:1).

[0042] Product characterization: 1 H NMR (400MHz, CDCl 3 )δ8.00–7.89(m,2H),7.82–7.71(m,2H),7.68–7.57(m,1H),7.53–7.43(m,2H),7.40–7.29(m,2H),4.72( s,2H),2.44(s,3H); 13 C NMR (101MHz, CDCl 3 ) δ 188.19, 145.41, 135.77, 134.36, 129.87, 129.35, 128.86, 128.63, 63.58, 21.74.

Embodiment 2

[0043] Example 2: 1-(4-methylphenyl)-2-p-toluenesulfonyl ethyl ketone

[0044]

[0045] Use 2-p-tolyl-3-phenyl-1-propene (104mg, 0.5mmol) to replace 2,3-diphenyl-1-propene, and the rest are the same as in Example 1, and the reaction operation is carried out to obtain the product (white Solid, yield 62%).

[0046] Product characterization: 1 H NMR (400MHz, CDCl 3 )δ7.85(d, J=8.2Hz, 2H), 7.76(d, J=8.3Hz, 2H), 7.34(d, J=8.0Hz, 2H), 7.28(d, J=8.5Hz, 2H) ,4.69(s,2H),2.45(s,3H),2.43(s,3H); 13 CNMR (101MHz, CDCl 3 ) δ 187.65, 145.59, 145.31, 135.65, 133.28, 129.80, 129.54, 129.50, 128.58, 63.52, 21.80, 21.73.

Embodiment 3

[0047] Example 3: 1-(biphenyl-4-yl)-2-p-toluenesulfonyl ethyl ketone

[0048]

[0049] Use 2-(biphenyl-4-yl)-3-phenyl-1-propene (135mg, 0.5mmol) to replace 2,3-diphenyl-1-propene, the rest are the same as in Example 1, and carry out the reaction operation , to obtain the product (white solid, yield 83%).

[0050] Product characterization: 1 H NMR (400MHz, CDCl 3 )δ8.03(d, J=8.4Hz, 2H), 7.78(d, J=8.2Hz, 2H), 7.71(d, J=8.4Hz, 2H), 7.63(d, J=7.2Hz, 2H) ,7.49(t,J=7.3Hz,2H),7.45–7.40(m,1H),7.35(d,J=8.0Hz,2H),4.75(s,2H),2.45(s,3H); 13 C NMR (101MHz, CDCl 3 )δ 187.68, 147.05, 145.45, 139.44, 135.65, 134.43, 130.04, 129.89, 129.06, 128.64, 128.62, 127.47, 127.35, 63.70, 21.78.

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Abstract

The invention discloses a preparation method of a beta-carbonyl sulfone compound, and belongs to the technical field of organic synthesis. The preparation method of the beta-carbonyl sulfone compoundis provided for solving the problems that in the prior art, operation is complex, the substrate range is narrow, and the functional group tolerance is poor. The preparation method comprises the stepsof taking a compound shown in formula I and a compound shown in formula II as raw materials, taking copper salt as a catalyst, carrying out reaction in an organic solvent, and after the reaction is completed, carrying out aftertreatment to obtain the beta-carbonyl sulfone compound. The preparation method is simple and convenient to operate, mild in reaction condition, wide in substrate range and good in functional group tolerance, the yield reaches up to 93%, and the synthesis cost is remarkably reduced.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of β-carbonyl sulfone compounds. Background technique [0002] β-carbonyl sulfone structural units are widely found in various drug molecules and natural products, and they often have good biological activities, such as anticancer, antitumor, antibacterial, anti-inflammatory, etc. Therefore, the construction of β-carbonyl sulfone structural units is in It has important application value in drug discovery and new drug development. In addition, as organic synthesis intermediates, β-carbonyl sulfone compounds can also be used to synthesize optically active β-hydroxy sulfone compounds, chiral lactones, tetrahydrofuran, γ-butyrolactone, N-heterocyclic compounds, etc. [0003] At present, the synthesis methods of β-carbonyl sulfone compounds are mainly divided into two types: traditional synthesis methods mostly use sulfinic acid and its salt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/00C07C317/24C07C317/44C07D333/34C07D213/71C07D307/46C07B45/04
CPCC07C315/00C07D333/34C07D213/71C07D307/46C07B45/04C07C317/24C07C317/44Y02P20/584
Inventor 易东韦思平张智杰何林颖戚仲钰付强卢戢魏军
Owner SOUTHWEST MEDICAL UNIVERISTY
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