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Fluorine-containing alpha, beta-unsaturated ketone and synthetic method thereof

A synthetic method and unsaturated technology, applied in the field of fluorine-containing α, can solve the problems of inconvenient operation, average yield, and expensive raw materials, and achieve the effects of high selectivity, less by-products, and less pollution

Inactive Publication Date: 2008-01-16
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] In summary, there are many methods for preparing fluorine-containing α, β-unsaturated ketones, but some raw materials are more expensive, some operations are not easy enough, and the yield is average.

Method used

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  • Fluorine-containing alpha, beta-unsaturated ketone and synthetic method thereof
  • Fluorine-containing alpha, beta-unsaturated ketone and synthetic method thereof
  • Fluorine-containing alpha, beta-unsaturated ketone and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0027] Example 1: Preparation of 1,1,1-trifluoro-4-(4-methyl-phenyl)-but-3-en-2-one

[0028] Add 1,1,1,5,5,5-hexafluoro-3-(4-methyl-styryl)-pentane-2,4-dione (310mg, 1mmol) in a 5ml eggplant-shaped bottle, Tetrahydrofuran (2ml), K 3 PO 4 ·3H 2 O (399mg, 1-5mmol), add a magnetic stirrer, under stirring, react at room temperature to 1,1,1,5,5,5-hexafluoro-3-(4-methyl-styryl)- Pentane-2,4-dione reacted completely, separated by column chromatography (developing solvent: ethyl acetate:petroleum ether=4:1), to obtain 1,1,1-trifluoro-4-(4- Methyl-phenyl)-but-3-en-2-one, the structure of the compound is:

[0029]

[0030] Molecular formula: C 11 h 9 f 3 o

[0031] Chinese name: 1,1,1-trifluoro-4-p-methylphenyl-3-en-2-one

[0032] English name: 1,1,1-trifluoro-4-p-tolybut-3-en-2-one

[0033] Molecular weight: 214.06

[0034] Appearance: light yellow liquid

[0035] Proton NMR spectrum (500MHz, CDCl 3 , internal standard: TMS): 2.42 (s, 3H, CH 3 ), 6.98 (d, J=16, 1H, CH...

example 2

[0037] Example 2: Preparation of 1,1,1-trifluoro-4-(4-methoxy-phenyl)-but-3-en-2-one

[0038] Add 1,1,1,5,5,5-hexafluoro-3-(4-methoxy-styryl)-pentane-2,4-dione (326mg, 1mmol) in a 5ml eggplant-shaped flask , tetrahydrofuran (2ml), K 3 PO 4 ·3H 2 O (532mg, 2mmol), add a magnetic stirrer, under stirring, react at room temperature to 1,1,1,5,5,5-hexafluoro-3-(4-methoxy-styryl)-pentane The reaction of alkane-2,4-dione was complete, and it was separated by column chromatography (developing solvent: ethyl acetate:petroleum ether=4:1) to obtain 1,1,1-trifluoro-4-(4-methoxy Base-phenyl)-but-3-en-2-one, the structure of the compound is:

[0039]

[0040] Molecular formula: C 11 h 9 f 3 o 2

[0041] Chinese name: 1,1,1-trifluoro-4-p-methoxyphenyl-3-en-2-one

[0042] English name: 1,1,1-trifluoro-4-(4-methoxyphenyl)but-3-en-2-one

[0043] Molecular weight: 230.06

[0044] Appearance: light yellow liquid

[0045] Proton NMR spectrum (500MHz, CDCl 3 , internal standard: TM...

example 3

[0047] Example 3: Preparation of 1,1,1-trifluoro-4-(2-furyl)-but-3-en-2-one

[0048] Add 1,1,1,5,5,5-hexafluoro-3-(2-furyl-vinyl)-pentane-2,4-dione (286mg, 1mmol), tetrahydrofuran into a 5ml eggplant-shaped bottle (2ml), K 3 PO 4 ·3H 2 O (798mg, 3mmol), add a magnetic stirrer, under stirring, react at room temperature to 1,1,1,5,5,5-hexafluoro-3-(2-furyl-vinyl)-pentane- The reaction of 2,4-diketone was complete, and it was separated by column chromatography (developing solvent: ethyl acetate:petroleum ether=4:1) to obtain 1,1,1-trifluoro-4-(4-methyl-benzene Base)-but-3-en-2-one, the structure of the compound is:

[0049]

[0050] Molecular formula: C 8 h 5 f 3 o 2

[0051] Chinese name: 1,1,1-trifluoro-4-(2-furyl)-3-en-2-one

[0052] English name: 1,1,1-trifluoro-4-(furan-2-yl)but-3-en-2-one

[0053] Molecular weight: 190.02

[0054] Appearance: light yellow liquid

[0055] Proton NMR spectrum (500MHz, CDCl 3 , internal standard: TMS): 6.57 (m, J=1.5, 3.5, 1H, f...

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Abstract

The invention relates to alpha, beta-unsaturated trifluoromethyl ketones and synthesis method thereof. The structure of the compound is showed in the right. Substituents Ar are 4- methyl-phenyl, 4-methoxyphenyl and 2-furan group. The steps of the method are that: dissolve beta, beta-erythrene (trifluoroacetyl group) derivatives and alkali K3PO4-3H2O in tetrahydrofuran according to a mol ratio of 1:1.5-3; stir the mixed solution under room temperature until the beta, beta-erythrene( trifluoroacetyl group) derivatives completely dissolve and then column-chromatograph the solution, in this way, pure alpha and beta-unsaturated trifluoromethyl ketones can be obtained. The invention takes simple alkali and beta, beta-erythrene (trifluoroacetyl group) derivatives which are easy to get as raw materials, reaction effect is good and side product is little with little pollution and high selectivity, thereby the method is an important way to synthesize alpha, beta-unsaturated trifluoromethyl ketones.

Description

technical field [0001] The invention relates to a fluorine-containing α, β-unsaturated ketone and a synthesis method thereof. Background technique [0002] Fluorinated organic compounds are potentially active substances used in pharmaceuticals and pesticides. In recent years, organofluorine chemistry has attracted extensive attention of scientists, especially the synthesis of simple and synthetically valuable fluorine-containing building blocks. Fluorine-containing unsaturated ketones are not only important intermediates in the synthesis of cyclic compounds, but also have pharmaceutical value in themselves. [0003] Generally speaking, after the fluorine atom is introduced into the compound, its physical, chemical properties and physiological activities will have great changes due to the pseudo-imitation effect and the blocking effect in the metabolic process. After introducing fluorine atoms or fluorine-containing groups into many drug molecules, many unexpected changes w...

Claims

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Application Information

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IPC IPC(8): C07C49/235C07C49/255C07C45/67C07D307/46
Inventor 钱嘉贤曹卫国张慧任仲皎陈杰
Owner SHANGHAI UNIV
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