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Method for selectively reducing alpha, beta-unsaturated ketone

An unsaturated and selective technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of long reaction time and low reaction conversion rate, and achieve easy operation, simplified experimental operation process, and production high rate effect

Pending Publication Date: 2020-11-13
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are disadvantages such as the use of noble metal catalysts, low reaction conversion rate, and long reaction time.

Method used

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  • Method for selectively reducing alpha, beta-unsaturated ketone
  • Method for selectively reducing alpha, beta-unsaturated ketone
  • Method for selectively reducing alpha, beta-unsaturated ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] 1 mmol chalcone was added to a 10 mL reaction test tube, a protic solvent was added to dissolve it completely, then 5% mol of Lews acid, 0.02 mmol of TMSCl and 1.0 mmol of triethylsilane were sequentially added, and the reaction was stirred at room temperature. When the reaction is complete, it is quenched and extracted with saturated sodium bicarbonate solution, and the organic layer is collected. Then, the solvent is removed by distillation under reduced pressure, and then dihydrochalcone can be obtained by recrystallization (petroleum ether:ethyl acetate=20:1 mixed solvent).

[0036] Characterization data

[0037] Dihydrochalcone: 1 H NMR (400 MHz, CDCl 3 ) δ 7.97 (m, 2H), 7.56 (m, 1H), 7.46 (m, 1H), 7.29 (m, 2H), 7.22 (m, 4H), 3.32 (m, 2H), 3.08 (m, 2H) ; 13 C NMR (101MHz, CDCl 3 ) δ 199.3, 141.3, 136.8, 133.1, 128.6, 128.1, 126.2, 40.5, 30.1.

Embodiment 2

[0039] Put 1mmol of 4'-hydroxy-2,4-dimethoxychalcone in a 10mL reaction test tube, add a protic solvent to dissolve it completely, then add 5% mol Lews acid, 0.02mmol TMSCl and 1.0mmol triethyl in turn silane, and the reaction was stirred at room temperature. When the reaction is complete, it is quenched with saturated sodium bicarbonate solution, and the organic layer is extracted and collected. Then, the solvent is removed by distillation under reduced pressure, and then recrystallized (petroleum ether: ethyl acetate = 3:1 mixed solvent) to obtain 4'-hydroxy-2,4-dimethoxydihydrochalcone (dragon's blood). prime A).

[0040] Characterization data

[0041] 4'-Hydroxy-2,4-dimethoxydihydrochalcone: 1 H NMR (400 MHz, CDCl 3 ) δ 7.92 (m, 2H), 7.08 (d, J = 8.1 Hz, 1H), 6.88 (m, 2H), 6.42 (m, 2H), 3.78 (d, J = 7.0 Hz, 6H), 3.17 (m , 2H), 2.96 (m, 2H); 13 C NMR (101 MHz, CDCl 3 ) δ 194.4, 155.3, 154.2, 153.1, 125.5, 125.1, 116.7, 110.1, 98.7, 93.4, 50.2, 50.00, 33.7, 20.2.

Embodiment 3

[0043] Put 1mmol of 1-(naphthalen-2-yl)-3-phenylpropen-2-en-1-one in a 10mL reaction test tube, add a protic solvent to make it completely dissolved, and then add 5% mol Lews acid, 0.02 mmol TMSCl and 1.0 mmol triethylsilane, and the reaction was stirred at room temperature. When the reaction is complete, it is quenched with saturated sodium bicarbonate solution, and the organic layer is extracted and collected. Then, the solvent is removed by distillation under reduced pressure, and the compound 1-(naphthalen-2-yl)-3-phenylpropan-1-one can be obtained by recrystallization (petroleum ether:ethyl acetate=15:1 mixed solvent).

[0044] Characterization data

[0045] 1-(Naphthalen-2-yl)-3-phenylpropan-1-one: 1 H NMR (400 MHz, CDCl 3 ) 8.38 (s, 1H), 7.96 (m, 1H), 7.87 – 7.77 (m, 3H), 7.49 (m, 2H), 7.23 (t, J = 4.3 Hz, 4H), 7.16 (d, J= 11.5 Hz, 1H), 3.36 (m, 2H), 3.11 – 2.97 (m, 2H); 13 C NMR (101 MHz, CDCl 3) δ198.2, 140.3, 134.5, 133.1, 131.5, 128.7, 128.5, 127.5, 127.4, 126...

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Abstract

The invention relates to the technical field of catalysts, in particular to a catalytic system for reducing alpha, beta-unsaturated ketone, and aims to selectively reducing alpha, beta-unsaturated ketone compounds under simple and mild conditions. The preparation method of the catalytic system is simple, TESH serves as a cheap, safe and environment-friendly hydrogen donor, Lewis acid / TMSCl servesas a reduction catalyst, a chemical selective hydrosilylation reaction is conducted on alpha, beta-unsaturated ketone compounds, and natural products such as loureirin A and loureirin B can be synthesized. The catalytic system has the characteristics of mild conditions, no use of strong acid or strong alkali, safety, high reaction conversion rate, and simple and convenient operation.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a method for selectively reducing α,β-unsaturated ketones. Background technique [0002] The selective reduction of α,β-unsaturated ketones is of great application and challenging. Since both carbon-carbon double bonds and carbonyl groups are prone to reduction reactions, the selective reduction of conjugated carbon-carbon double bonds in α,β-unsaturated ketone compounds still has certain limitations. The reduction reaction occurs simultaneously, so that the conversion of the reaction is not high. [0003] At the same time, the method for selectively reducing α,β-unsaturated ketone compounds has problems such as high price, harsh reaction conditions, and easy environmental pollution, and there is still room for improvement in the synthesis method thereof. The traditional method of reducing α, β-unsaturated ketones generally introduces hydrogen as a reducing agent, and obtains...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/62C07C49/784C07C49/84C07C49/796
CPCC07C45/62C07C49/784C07C49/84C07C49/796
Inventor 黄超林俊洁王爽杨丽娟
Owner YUNNAN MINZU UNIV
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