1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone and preparation method thereof

A ferrocene-based and cyclopentanone-based technology, which is applied to chemical instruments and methods, metallocenes, and organic iron compounds, can solve the problems of large solvent usage, low yield, and long reaction time, and achieve the goal of reaction The effect of short time, simple reaction process and low equipment requirements

Inactive Publication Date: 2015-03-25
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-(2-cyclopentanon)-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Weigh 0.0012mol cyclopentanone, 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 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, which is 1-2 Ferrocenyl-3-phenyl-3-(2-cyclopentanonyl)-propanone. Yield 85%, m.p. 115°C-116°C.

[0055] IR (KBr tablet, v / cm -1 ):2920, 1724, 1654, 1595, 1528, 1486, 1384;

[0056] 1 H-NMR: 7.14-7.85 (m, 5H, Ar-H), 4.87 (s, 2H, C 5 h 4 ), 4.50(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 3.20-3.65 (m, 2H, CH 2 CH 2 ), 2.03(d,2H,-COCH 2 ), 1.27(m, 1H, -CH);

[0057] 13 C-NMR: 192.5, 140.4, 134.2, 126.3, 125.6, 122.5, 43.6, 40.0, 38.4, 27.8, 27.0.

Embodiment 2

[0059] Weigh 0.0012mol cyclopentanone, 0.0012mol anhydrous K 2 CO 3 Put it in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-(p-chlorophenyl)-propenone, mix and grind. The mixture will 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-(2-cyclopentanonyl)-propanone. Yield 82%, m.p. 111°C-112°C.

[0060] IR (KBr tablet, v / cm -1 ):2923, 1728, 1663, 1591, 1521, 1448, 1387;

[0061] 1 H-NMR: 7.28-7.78 (m, 4H, Ar-H), 4.90 (s, 2H, C 5 h 4 ), 4.50(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 3.15-3.99 (m, 2H, CH 2 CH 2 ), 2.02(d, 2H, -COCH 2 ), 1.27(m, 1H, -CH);

[0062] 13 C-NMR: 192.3, 142.1, 140.9, 129.6, 129.4, 128.9, 128.1, 51.8, 40.2, 38.4, 28.7, 27.6.

Embodiment 3

[0064] Weigh 0.0012mol cyclopentanone, 0.0012mol anhydrous K 2 CO 3 Place in a mortar and mix quickly and uniformly, then add 0.001mol 1-ferrocenyl-3-(p-bromophenyl)-propenone, mix and grind. The mixture will 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-(2-cyclopentanonyl)-propanone. Yield 80%, m.p. 108°C-109°C.

[0065] IR (KBr tablet, v / cm -1 ):2929, 1729, 1663, 1591, 1518, 1490, 1401;

[0066] 1 H-NMR: 7.03-7.49 (m, 4H, Ar-H), 4.85 (s, 2H, C 5 h 4 ), 4.52(s, 2H, C 5 h 4 ), 4.25(s, 5H, C 5 h 5 ), 3.14-3.62 (m, 2H, CH 2 CH 2 ), 2.02(d, 2H, -COCH 2 ), 1.27(m, 1H, -CH);

[0067] 13 C-NMR: 192.8, 140.2, 138.7, 136.5, 130.9, 129.8, 129.7, 52.1, 43.2, 38.6, 29.7, 27.1.

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Abstract

The invention discloses 1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone and a preparation method thereof. The structural formula of the 1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone is shown in the specification. The preparation method of the 1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone comprises the following steps: adding A mol of 1-ferrocenyl-3-aryl-acrylketone, B mol of anhydrous K2CO3 (or NaOH) and C mol of cyclopentanone into a dry mortar to quickly grind; performing TLC (Thin Layer Chromatography) monitoring until the reaction is complete; then washing, performing extraction filtration and drying to obtain the 1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone. The invention provides the1-ferrocenyl-3-aryl-3-(2-cyclopentanon)-acetone and the preparation method thereof. The method has the advantages of short reaction time, no need of solvent, environment friendliness, economy, easiness in operation, mild reaction condition, easiness in post-treatment and high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-(2-cyclopentanonyl)-acetone and a preparation method thereof. Background technique [0002] The traditional Michael addition reaction uses a solvent method, the reaction time is long and the amount of solvent is large, which greatly increases the reaction cost; in recent years, microwave radiation, ultrasonic radiation, and solid-phase synthesis have been used in Michael addition reaction. In recent years, environmental protection has attracted more and more attention, and green synthesis has become the first choice for organic synthesis. Among them, solid-phase organic synthesis is favored by researchers because it avoids the use of organic solvents, has short reaction time and good selectivity, and is an ideal organic synthesis method. [0003] Based on this, there is no literature report on the synthesis of a series of Michael addition produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02
CPCC07F17/02
Inventor 尹大伟宋思梦刘玉婷尹静怡杨阿宁王金玉刘蓓蓓王雨薇
Owner SHAANXI UNIV OF SCI & TECH
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