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Method for synthesizing alpha-seleno-alpha, beta-unsaturated carbonyl compound from organic sodium selenosulfate

A carbonyl compound and sodium sulfosulfate technology, applied in organic chemistry and other fields, can solve problems such as high environmental hazards, increased costs, and small substrate range

Active Publication Date: 2021-05-18
NANJING UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] There are some disadvantages in the above method, such as limited raw materials, a small range of substrates, or the unavoidable use of stinky selenium halide compounds, some reactions require the use of metal catalysts and additives, which also increases the cost of the reaction, It is harmful to the environment and does not conform to the development direction of green chemistry

Method used

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  • Method for synthesizing alpha-seleno-alpha, beta-unsaturated carbonyl compound from organic sodium selenosulfate
  • Method for synthesizing alpha-seleno-alpha, beta-unsaturated carbonyl compound from organic sodium selenosulfate
  • Method for synthesizing alpha-seleno-alpha, beta-unsaturated carbonyl compound from organic sodium selenosulfate

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Experimental program
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Effect test

Embodiment 1

[0028] Add 0.073g (0.5mmol) benzylidene acetone, 0.2055g (0.75mmol) sodium benzylselenosulfate, 0.0254g (0.1mmol) iodine and 2mL (25mmol) dimethylsulfoxide to a 35mL thick-walled pressure-resistant tube . The reaction was stirred at 70°C for 8h. After the reaction, the reaction solution was diluted with 20 mL of water, extracted three times with 15 mL of ethyl acetate, the organic phases were combined, washed with saturated brine, the organic phase was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product was separated by column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate, the volume ratio of the two was 10:1) to obtain 0.1153 g of α-benzylselenyl-benzylidene acetone, with a yield of 73% .

[0029] α-Benzylidene-benzylideneacetone 1 H NMR and 13 C NMR data are as follows.

[0030] 1 H NMR (500MHz, Chloroform-d) δ7.53(d, J=15.9Hz, 1H), 7.48–7.45(m, 2H), 7.34–7.28(m, 4H)...

Embodiment 2

[0033] Add 0.073g (0.5mmol) chromone, 0.195g (0.75mmol) sodium phenylselenosulfate, 0.0254g (0.1mmol) iodine and 2mL (25mmol) dimethylsulfoxide into a 35mL thick-walled pressure-resistant tube. The reaction was stirred at 70°C for 8h. After the reaction, the reaction solution was diluted with 20 mL of water, extracted three times with 15 mL of ethyl acetate, the organic phases were combined, washed with saturated brine, the organic phase was separated, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product was separated by column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate, the volume ratio of which was 20:1) to obtain 0.1042 g of α-phenylselenyl-chromone with a yield of 69%.

[0034] α-Phenylselenyl-chromone 1 H NMR and 13 C NMR data are as follows.

[0035] 1 H NMR (500MHz, Chloroform-d) δ8.23 (d, J = 8.0Hz, 1H), 7.88 (d, J = 0.9Hz, 1H), 7.70-7.56 (m, 3H), 7.41 (dd, J = 9.7,8.2Hz...

Embodiment 3

[0038] This embodiment is basically the same as Embodiment 1, the only difference is that the reaction temperature is 60°C. The yield was 68%.

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Abstract

The invention discloses a method for synthesizing an alpha-seleno-alpha, beta-unsaturated carbonyl compound from organic sodium selenosulfate. According to the method, an alpha, beta-unsaturated carbonyl compound and organic sodium selenosulfate are taken as raw materials, dimethyl sulfoxide is taken as a solvent under the catalysis of iodine, and the alpha-seleno-alpha, beta-unsaturated carbonyl compound is prepared through full reaction at the temperature of 60-80 DEG C. The method is reasonable in process condition and simple and safe to operate; and raw materials such as selenol with unpleasant smell are avoided, a metal catalyst is not needed, and the method is environment-friendly.

Description

technical field [0001] The invention relates to the field of organic synthesis, and relates to a method for synthesizing α-seleno-α, β-unsaturated carbonyl compounds from organic sodium selenosulfate. Background technique [0002] α-selenyl-α, β-unsaturated carbonyl compound is an important synthetic intermediate in the field of organic synthesis. It can form the corresponding 1,3-diene through Wittig reaction, and then carry out the allyl group of selenoyl[2 ,3]-σ rearrangement can generate the corresponding α-propadiene, α-propadiene amine or α-propadiene chloride, or directly as a conjugated diene and alkene to undergo a heteroatom Diels-Alder reaction to generate The corresponding dihydropyrans. In addition, α-selenyl-α,β-unsaturated carbonyl compounds can also participate in subsequent reactions as Z-allyl precursors to maintain configuration. Therefore, the synthesis of α-seleno-α,β-unsaturated carbonyl compounds is an important topic in organic synthesis. Many synt...

Claims

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Application Information

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IPC IPC(8): C07C391/00C07D311/22
CPCC07C391/00C07D311/22
Inventor 仇晃耀张志国易文斌刘帆敏赫五卷
Owner NANJING UNIV OF SCI & TECH
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