1-ferrocenyl-3-aryl-3-nitromethylene-acetone and preparation method thereof

A nitromethylene and ferrocene-based technology, 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: 2015-01-07
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-nitromethylene-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-nitromethylene-acetone and preparation method thereof
  • 1-ferrocenyl-3-aryl-3-nitromethylene-acetone and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0043] A preparation method of 1-ferrocenyl-3-aryl-3-nitromethylene-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 nitromethane is added into a dry mortar and ground rapidly at room temperature until the reaction is completed, the grinding time is 5-10min, and TLC is used to detect the reaction process during the reflection. 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, and the crude product will be obtained after the reaction is complete.

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

Embodiment 1

[0049] Weigh 0.0012mol nitromethane, 0.0012mol anhydrous K 2 CO 3 Place in a mortar and mix quickly and evenly, then add 0.001mol 1-ferrocenyl-3-phenyl-propenone, mix and grind at room temperature for 10 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, and dry in vacuum at 25°C for 24 hours to obtain a dark red solid, namely 1- Ferrocenyl-3-phenyl-3-nitromethylene-acetone. The m.p. is 129°C-130°C.

[0050] IR (KBr tablet) ν (cm -1 ): 3089, 1684, 1452, 1375, 1340; 1 H NMR: 7.14-7.85 (m, 5H, Ar-H), 4.62-4.94 (m, 9H, Cp), 4.14-4.24 (d, 1H, CH), 2.42-2.50 (m, 1H, ...

Embodiment 2

[0052] Weigh 0.0012mol nitromethane, 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 5 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 is 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, and then vacuum dry. The vacuum drying temperature is 25 ° C and the time is 24 hours. That is, 1-ferrocenyl-3-(p-chlorophenyl)-3-nitromethylene-acetone was obtained. The m.p. is 86°C-87°C.

[0053] IR (KBr tablet) ν (cm -1 ): 3086, 1652, 1449, 1370, 1342, 819; 1 H N...

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Abstract

The invention discloses a 1-ferrocenyl-3-aryl-3-nitromethylene-acetone and a preparation method thereof. The structural formula of the compound is disclosed in the specification. The preparation method comprises the following steps: quickly grinding 1-ferrocenyl-3-aryl-propenylketone, anhydrous K2CO3 (or NaOH) and nitromethane in a dry mortar, and detecting the reaction progress by TLC (thin layer chromatography); and after the reaction is completely finished, washing with water, carrying out vacuum filtration and vacuum drying to obtain the 1-ferrocenyl-3-aryl-3-nitromethylene-acetone. The invention provides the 1-ferrocenyl-3-aryl-3-nitromethylene-acetone and the preparation method thereof. The method is simple to operate, and has the advantages of mild reaction conditions, simple after-treatment, no need of solvent, high economy and high yield; and the prepared product is a brand-new ketone and can be used in the fields of pesticides, medicines 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-nitromethylene-acetone and a preparation method thereof. Background technique [0002] Michael addition is a nucleophilic addition reaction of an enolate (or similar) anion to a, β-unsaturated ketone, aldehyde, ester or carboxylic acid derivative carbon-carbon double bond, and is also an active methylene compound A method of alkylation reaction, which is a classic organic reaction. With the development of organic synthesis methods, heteronuclear Michael addition with nucleophiles such as nitrogen, sulfur, and oxygen as donors can also be realized, and Michael addition has become one of the important methods for the synthesis of C-C, C-O, C-N, and C-S bonds. During the Michael addition reaction, the addition of the nucleophile (donor) to the β-position of the acceptor converts the β-carbon from the sp 2 hybridization to sp 3 Hybridization, in p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A01P1/00A61P31/00A61P29/00
CPCC07F17/02
Inventor 刘玉婷宋思梦尹大伟杨阿宁王金玉刘蓓蓓
Owner SHAANXI UNIV OF SCI & TECH
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