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1-Ferrocenyl-3-aryl-3-diacetylmethylene-acetone and preparation method thereof

A technology of diacetylmethine and ferrocenyl, which is applied in the field of chemical synthesis, can solve the problems of low yield, long reaction time, and large amount of solvent used, and achieve simple reaction process, short reaction time, and equipment less demanding effect

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

AI Technical Summary

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-3-aryl-3-diacetylmethylene-acetone and preparation method thereof
  • 1-Ferrocenyl-3-aryl-3-diacetylmethylene-acetone and preparation method thereof
  • 1-Ferrocenyl-3-aryl-3-diacetylmethylene-acetone and preparation method thereof

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preparation example Construction

[0043] A preparation method of 1-ferrocenyl-3-aryl-3-diacetylmethine-acetone, comprising the following steps:

[0044] Step 1) A mol1-ferrocenyl-3-aryl-propenone, B mol anhydrous K 2 CO 3 (or NaOH), C mol acetylacetone was added into a dry mortar and ground rapidly at room temperature until the reaction was completed, the grinding time was 5-10min, and TLC was used to detect the reaction process during the reaction. When 1-ferrocenyl-3-aryl- When the raw material point of acryl ketone 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.

[0045] Step 2) The crude product was washed with water and suction filtered several times, and was washed with water until the pH value of the filtrate was neutral, and the filter cake was vacuum-dried at a temperature of 20-30° C. for 20-30 hours to obtain 1-dim...

Embodiment 1

[0049] Weigh 0.0012mol acetylacetone, 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 at room temperature for 9 minutes. The mixture will start to become viscous as the reaction proceeds, 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-phenyl-propenone disappears, it indicates that the raw material Complete reaction, after the reaction is completed, wash and filter with pure water several times, wash with water until the pH value of the filtrate is neutral, vacuum dry, vacuum dry, vacuum drying temperature is 25 ° C, time 24h, to obtain a reddish-brown solid, namely 1-Ferrocenyl-3-phenyl-3-diacetylmethine-acetone was obtained. The m.p. is 106°C-108°C.

[0050] IR (KBr tablet) ν (cm -1 ): 3100, 2937, 2869, 1712, 1391; 1 H NMR: 7.09-8.01 (m, 5H, Ar-H), 4.45-4.93 (m, ...

Embodiment 2

[0052] Weigh 0.0012mol acetylacetone, 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 8 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 materials are completely reacted. After the reaction is completed, wash and filter with pure water for many times. When filtering, wash with water until the pH value of the filtrate is neutral. Then vacuum dry. The vacuum drying temperature is 25 ° C and the time is 24 hours. Red solid, that is, 1-ferrocenyl-3-(p-chlorophenyl)-3-diacetylmethine-acetone. The m.p. is 147°C-150°C.

[0053] IR (KBr tablet) ν (cm -1 ): 3150, 2971, 2839, 1647, 1374, 825; 1 H N...

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Abstract

The invention discloses 1-ferrocenyl-3-aryl-3-diacetylmethylene-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 acetylacetone 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 to obtain 1-ferrocenyl-3-aryl-3-diacetylmethylene-acetone. The method has the advantages of 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 in the fields of pesticides and medicines.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 1-ferrocenyl-3-aryl-3-diacetylmethine-acetone and a preparation method thereof. Background technique [0002] Traditional organic synthesis methods have disadvantages such as high energy consumption, low yield, and serious environmental pollution, which do not meet people's requirements for "green chemistry" in recent years. Michael addition is one of the important reactions for building carbon-carbon bonds in organic synthesis, so it has always been a research topic of interest to organic synthetic chemists. In recent years, organocatalytic asymmetric Michael addition reactions have developed rapidly and become a new hotspot in the field of asymmetric catalysis research. [0003] Chalcones are a class of unsaturated carbonyl compounds with aromatic rings at both ends. The variability of the aromatic groups at both ends endows this type of compound with the character...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61P31/00A01P1/00A01P3/00
CPCC07F17/02
Inventor 尹大伟宋思梦刘玉婷田丹杨阿宁王金玉刘蓓蓓
Owner SHAANXI UNIV OF SCI & TECH
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