1-ferrocenyl-3-aryl-3-cyano-methylene-acetone and preparation method thereof

A technology based on nitrile methylene and ferrocenyl, applied in chemical instruments and methods, metallocenes, chemicals for biological control, etc., can solve the problem of large solvent usage, low yield and long reaction time and other problems, to achieve the effect of short reaction time, simple reaction process and low equipment requirements

Inactive Publication Date: 2015-04-01
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, the preparation of existing ketone compounds is mostly based on the liquid phase reflux method, which has the disadvantages of long reaction time, low yield, and large solvent usage.

Method used

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  • 1-ferrocenyl-3-aryl-3-cyano-methylene-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-cyano-methylene-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-cyano-methylene-acetone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Weigh 0.0012mol acetonitrile, 0.0012mol anhydrous K 2 CO 3Put it in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-phenyl-propenone, mix and grind. The mixture will start to become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin layer chromatography to monitor the reaction progress. After the reaction is completed, wash with pure water several times and filter to obtain a reddish-brown solid, that is, 1-2 Ferrocenyl-3-phenyl-3-cyanomethylene-acetone. m.p.128℃~130℃.

[0058] IR (KBr tablet, v / cm -1 ):2919, 2245, 1782, 1647, 1592, 1450;

[0059] 1 H-NMR: 7.17-7.83 (m, 5H, Ar-H), 4.96 (s, 2H, C 5 h 4 ), 4.54(s, 2H, C 5 h 4 ), 4.26(s, 5H, C 5 h 5 ), 2.04(d, 2H, COCH 2 ), 1.68 (d, 2H, CH 2 );

[0060] 13 CNMR: 192.3, 140.4, 135.8, 129.7, 128.5, 127.8, 122.5, 43.4, 35.4.

Embodiment 2

[0062] Weigh 0.0012mol acetonitrile, 0.0012mol anhydrous K 2 CO 3 Place in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-(p-chlorophenyl)-propenone, mix and grind. The mixture will start to become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-(p-chlorophenyl)-3-cyanomethylene-acetone. m.p.149℃~150℃.

[0063] IR (KBr tablet, v / cm -1 ):2917, 2245, 1784, 1649, 1588, 1451;

[0064] 1 H-NMR: 7.09-7.78 (m, 4H, Ar-H), 4.94 (s, 2H, C 5 h 4 ), 4.63 (s, 2H, C 5 h 4 ), 4.24(s, 5H, C 5 h 5 ), 3.06 (d, 2H, COCH 2 ), 2.43 (d, 2H, CH 2 );

[0065] 13 CNMR: 201.9, 149.7, 138.6, 136.4, 126.1, 125.1, 30.7, 30.0.

Embodiment 3

[0067] Weigh 0.0012mol acetonitrile, 0.0012mol anhydrous K 2 CO 3 Place in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-(p-bromophenyl)-propenone, mix and grind. The mixture will start to become viscous as the reaction proceeds. Continue to grind until the substance does not change. Use thin-layer chromatography to monitor the reaction progress. After the reaction is completed, wash with pure water several times and filter to obtain a dark red solid, which is 1-2 Ferrocenyl-3-(p-bromophenyl)-3-cyanomethylene-acetone. m.p.160℃~162℃.

[0068] IR (KBr tablet, v / cm -1 ):2917, 2243, 1786, 1649, 1587, 1450;

[0069] 1 H-NMR: 7.12-7.77 (m, 4H, Ar-H), 4.94 (s, 2H, C 5 h 4 ), 4.64(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 2.06(d, 2H, COCH 2 ), 1.69 (d, 2H, CH 2 );

[0070] 13 CNMR: 192.3, 138.9, 133.6, 131.7, 129.2, 123.0, 43.6, 35.2.

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Abstract

The invention discloses 1-ferrocenyl-3-aryl-3-cyano-methylene-acetone and a preparation method thereof. 1-ferrocenyl-3-aryl-3-cyano-methylene-acetone has a structural formula described in the description. The preparation method comprises the following steps: adding A mol of 1-ferrocenyl-3-aryl-acrylketone, B mol of anhydrous K2CO3 (or NaOH) and C mol of acetonitrile into a dried mortar, quickly grinding, performing TLC (Thin Layer Chromatography) detection until complete reaction, washing with water, performing suction filtration, and drying to obtain 1-ferrocenyl-3-aryl-3-cyano-methylene-acetone. The preparation method has the advantages of being short in reaction time, free of solvent, environment friendly, good in economic property, simple in operation, mild in reaction conditions, simple in after-treatment and high in yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-nitrile methylene-acetone and a preparation method thereof. Background technique [0002] The Michael addition reaction is a typical nucleophilic addition reaction. In the reaction process, an active H is first taken away to generate a carbanion, and then the carbanion attacks the carbon atom in the α, β-unsaturated carbonyl compound for nucleophilic addition. into a reaction. The compounds that can form nucleophilic carbanions are called donors, and the electrophilic α,β-unsaturated conjugated systems are called acceptors. [0003] In recent years, green chemistry has been widely concerned by the chemical community, and green synthesis has also become the first choice for organic synthesis workers. Solid-phase organic synthesis is an important part of green synthesis, because it does not use solvents in the reaction process, avoids the danger a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A01P1/00A01P3/00A01P13/00
CPCC07F17/02
Inventor 刘玉婷宋思梦尹大伟尹静怡杨阿宁王金玉刘蓓蓓吴倩倩
Owner SHAANXI UNIV OF SCI & TECH
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