1-Ferrocenyl-aryl-3-(1-cyan-1-ethyl formate-methylene)-acetone and preparation method thereof

An ethyl formate-based, ferrocene-based technology, applied in chemical instruments and methods, metallocenes, antipyretics, etc., can solve the problems of low yield, long reaction time, large amount of solvent, etc. Simple process, short response time and low equipment requirements

Inactive Publication Date: 2015-01-28
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The preparation of existing chalcone compounds has the disadvantages of long reaction time, low yield, large solvent usage, etc.

Method used

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  • 1-Ferrocenyl-aryl-3-(1-cyan-1-ethyl formate-methylene)-acetone and preparation method thereof
  • 1-Ferrocenyl-aryl-3-(1-cyan-1-ethyl formate-methylene)-acetone and preparation method thereof
  • 1-Ferrocenyl-aryl-3-(1-cyan-1-ethyl formate-methylene)-acetone and preparation method thereof

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preparation example Construction

[0047] A preparation method of 1-ferrocenyl-3-aryl-3-(1-cyano-1-formyl ethyl-methine)-acetone, comprising the following steps:

[0048] Step 1) Amol 1-ferrocenyl-3-aryl-propenone, B mol anhydrous K 2 CO 3(or NaOH), C mol ethyl cyanoacetate was added into a dry mortar and ground rapidly at room temperature until the reaction was completed. The grinding time was 5-10 min. During the reaction, TLC was used to detect the reaction process. When 1-ferrocenyl-3-aryl When the raw material point of base-propenone disappears, it means that the raw material has completely reacted; the developer of TLC is a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:3. After the reaction is complete, the crude product is obtained.

[0049] Step 2) The crude product is washed with water and suction filtered several times. During the suction filtration, it is washed with water until the pH value of the filtrate is neutral, and the filter cake is vacuum-dried. The vacuum dry...

Embodiment 1

[0053] Weigh 0.0012mol ethyl cyanoacetate, 0.0012mol anhydrous K 2 CO 3 Put it in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-phenylpropenone, mix and grind at room temperature for 5 minutes. The mixture will start to become viscous as the reaction progresses, continue to grind until the material no longer changes, monitor the progress of the reaction using thin layer chromatography (TLC), when the starting point of 1-ferrocenyl-3-phenylpropenone disappears Indicates that the raw materials have completely reacted. After the reaction is completed, add a small amount of ethyl acetate to dissolve, filter, and concentrate the filtrate to dryness to obtain a dark red solid, which is 1-ferrocenyl-3-phenyl-3-(1-cyano- 1-Ethylcarboxy-methine)-acetone. m.p. (melting point): 62°C-63°C.

[0054] IR (KBr tablet) ν (cm-1): 2983, 2260, 1783, 1665, 1370, 1345; 1 H NMR: 7.29-7.68 (m, 5H, Ar-H), 4.39-4.94 (m, 9H, Cp), 3.63-3.96 (d, 1H, CH), 3.32-3.40 (m, 1H, CH), ...

Embodiment 2

[0056] Weigh 0.0012mol ethyl cyanoacetate, 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 at room temperature for 10 minutes. The mixture will start to become viscous as the reaction progresses, continue to grind until the substance no longer changes, use thin layer chromatography to monitor the reaction progress, when the raw material point of 1-ferrocenyl-3-(p-chlorophenyl)-propenone When it disappears, it means that the raw material has completely reacted. After the reaction is completed, add a small amount of ethyl acetate to dissolve, filter, and concentrate the filtrate to dryness to obtain a dark red solid, which is 1-ferrocenyl-3-(p-chlorophenyl)-3- (1-Cyano-1-carboxyethyl-methine)-acetone. m.p.: 75°C-76°C.

[0057] IR (KBr tablet) ν (cm -1 ): 3090, 2253, 1738, 1653, 1372, 1348, 820; 1 H NMR: 7.14-7.76 (m, 5H, Ar-H), 4.38-5.28 (m, 9H, Cp), 4.11-4.19 (d, 1H, CH), ...

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Abstract

The invention discloses 1-ferrocenyl-aryl-3-(1-cyan-1-ethyl formate-methylene)-acetone and a preparation method thereof. The structural formula of the above compound is shown in the specification. The preparation method comprises the following steps: adding 1-ferrocenyl-3-aryl-acrylketone, anhydrous K2CO3 (or NaOH) and ethyl cyanoacetate into a dry mortar, rapidly grinding, detecting the reaction process through TLC, washing with water after the reaction, carrying out pumping filtration, and carrying out vacuum drying, or dissolving by using a small amount of ethyl acetate, carrying out pumping filtration, and concentrating the obtained filtrate until dryness in order to obtain 1-ferrocenyl-aryl-3-(1-cyan-1-ethyl formate-methylene)-acetone. The method has the advantages of small dosage of raw materials, simple operation, mild reaction conditions, simple post-treatment and high yield, and the product prepared in the invention is a brand new ketone, and can be used for sterilization, bacteriostasis, pain easing, inflammation prevention and the like.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-(1-cyano-1-formyl ethyl-methine)-acetone and a preparation method thereof. Background technique [0002] In organic chemistry, the conjugated addition of carbanions to a, β-unsaturated conjugated systems (aldehydes, ketones, esters, nitriles and nitro compounds, etc.) is called Michael (Michael) addition reaction. Usually, the compound that can form nucleophilic carbanion is called donor, and the electrophilic α, β-unsaturated conjugated system is called acceptor. Generally expressed by the following formula: [0003] [0004] Among them, y represents an electron-withdrawing group that can be conjugated with C=C, such as -CHO, -COR, -COOR, -CN and -NO2, etc.; HR represents a compound containing active hydrogen, which is a donor, including Lewis protonic acid , aldehydes, ketones or esters containing a-H and substances with electron-withdrawi...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61P29/00A61P31/00
CPCC07F17/02
Inventor 尹大伟宋思梦刘玉婷靖春燕杨阿宁王金玉刘蓓蓓
Owner SHAANXI UNIV OF SCI & TECH
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