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Synthesis method of (E)-1-styrylcyclohexane-1-nitrile compound

The technology of a styryl group and a synthesis method is applied in the synthesis field of alkene nitrile compounds, can solve the problems of low product yield, low atom utilization rate, unfriendly environment, etc., achieves high atom utilization rate and avoids waste of metal catalysts the effect of avoiding the use of toxic solvents

Active Publication Date: 2020-08-07
新疆普禾粟新型环保材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these azodinitrile-based reactions mainly rely on metal salt catalysis, and the solvents in the reaction (such as pyridine or xylene, etc.) are not environmentally friendly, and the product yield is not high, and the atom utilization rate is low. Therefore, the metal-catalyzed addition cyanation of alkynes and the decarboxylation cyanation of unsaturated acids are not ideal for the synthesis of acrylonitrile compounds.

Method used

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  • Synthesis method of (E)-1-styrylcyclohexane-1-nitrile compound
  • Synthesis method of (E)-1-styrylcyclohexane-1-nitrile compound
  • Synthesis method of (E)-1-styrylcyclohexane-1-nitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Raw materials: styrene;

[0047] Product: (E)-1-styrylcyclohexane-1-carbonitrile

[0048]

[0049] Eluent PE / EA=60:1. 87mg of light yellow oily liquid product was obtained, the yield was 82%.

[0050] 1 H NMR (400MHz, CDCl 3 )δ7.38(d, J=7.3Hz, 2H), 7.33(t, J=7.1Hz, 2H), 7.27(d, J=7.6Hz, 1H), 6.80(d, J=16.0Hz, 1H) ,6.01(d,J=16.0Hz,1H),2.03(d,J=11.9Hz,2H),1.85–1.67(m,4H),1.72(d,J=12.9Hz,2H),1.52(t, J=12.5Hz, 2H). 13 C NMR (101MHz, CDCl 3 )δ135.97, 130.28, 130.16, 128.64, 128.03, 126.50, 122.07, 41.62, 36.35, 24.86, 22.85. m / z=211.

Embodiment 2

[0052] Raw material: 4-methylstyrene;

[0053] Product: (E)-1-(4-methylstyryl)cyclohexane-1-carbonitrile

[0054]

[0055] Eluent PE / EA=60:1. 94 mg of bright yellow oily liquid product was obtained, with a yield of 84%.

[0056] 1 H NMR (400MHz, CDCl 3 )δ7.30(d, J=7.6Hz, 2H), 7.16(d, J=7.6Hz, 2H), 6.79(d, J=16.0Hz, 1H), 5.99(d, J=16.0Hz, 1H) ,2.36(s,3H),2.04(d,J=13.1Hz,2H),1.74(dd,J=26.8,13.2Hz,5H),1.53(t,J=12.3Hz,2H),1.40–1.06( m,1H). 13 C NMR (101MHz, CDCl 3 )δ137.76, 133.08, 129.85, 129.18 (d, J=3.8Hz), 126.28, 122.01, 41.42, 36.25, 24.75, 22.75, 21.04.m / z=225.

Embodiment 3

[0058] Raw material: 4-chlorostyrene;

[0059] Product: (E)-1-(4-chlorostyryl)cyclohexane-1-carbonitrile

[0060]

[0061] Eluent PE / EA=60:1. 106 mg of dark yellow oily liquid product was obtained with a yield of 87%.

[0062] 1 H NMR (400MHz, CDCl 3 )δ7.29(s,4H),6.75(d,J=16.0Hz,1H),5.99(d,J=16.0Hz,1H),2.02(d,J=13.1Hz,2H),1.87–1.62( m,5H), 1.52(t,J=12.5Hz,2H),1.35–0.97(m,1H). 13 C NMR (101MHz, CDCl 3 )δ134.47, 133.67, 130.93, 129.00, 128.76, 127.70, 121.83, 41.62, 36.28, 24.81, 22.80. m / z=245.

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Abstract

The invention discloses a synthesis method of (E)-1-styrylcyclohexane-1-nitrile compounds, wherein the synthesis method comprises the step: carrying out one-pot reaction on styrene compounds and ACCNin a DMSO solvent system under the catalysis of elemental iodine to obtain the (E)-1-styrylcyclohexane-1-nitrile compound. The method does not need to adopt a metal catalyst and a toxic solvent, is beneficial to environmental protection, mild in reaction condition, simple in step, high in target product yield, high in atom utilization rate and beneficial to industrial production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of alkene nitrile compound, particularly relate to a kind of (E)-1-styryl cyclohexane-1- A method for nitrile compounds belongs to the field of organic synthesis. Background technique [0002] Acrylonitrile compounds are important compounds widely present in pharmaceutical products, such as vitamin D receptors, pesticides and anti-HIV drugs, etc. In addition, since the cyano groups in acrylonitrile compounds can be easily converted into functional groups such as amines, amides and carboxylic acids through chemical reactions such as addition, hydrolysis, and reduction, acrylonitrile compounds and other cyano groups ( CN) compounds have been widely used as universal intermediates for the introduction of modified functional groups such as amines, amides and carboxylic acids. Therefore, the attention of chemists on acrylonitrile compounds remains high. [0003] Over the past few decades, effort...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/46C07B60/00
CPCC07C253/30C07B61/02C07C2601/14C07B2200/03C07C255/46
Inventor 郭灿城曹仲重郭欣
Owner 新疆普禾粟新型环保材料有限公司
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