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4-methyl-4-phenylcyclopentenone compound and preparation method thereof

A technology of phenylcyclopentenone and compound, applied in the field of 4-methyl-4-phenylcyclopentenone compound and preparation thereof, can solve problems such as transition metal activation, achieve mild reaction conditions and simple process conditions , the effect of good substrate suitability and functional group tolerance

Active Publication Date: 2020-02-07
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The object of the present invention is to provide a 4-methyl-4-phenylcyclopentenone compound and a preparation method thereof, aiming to solve the problem that the existing method uses a transition metal to activate the carbon-carbon triple bond

Method used

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  • 4-methyl-4-phenylcyclopentenone compound and preparation method thereof
  • 4-methyl-4-phenylcyclopentenone compound and preparation method thereof
  • 4-methyl-4-phenylcyclopentenone compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0031] (1) Under an inert gas atmosphere, add tetrahydrofuran (1.0ml, concentration 5mol / L) of acetaldehyde into a low-temperature reactor at -30°C, and add a tetrahydrofuran solution of ethynylmagnesium bromide dropwise under stirring (12ml , concentration 0.5mol / L, titration rate 1.0ml / min); after the reaction finishes, add excess saturated ammonium chloride solution to quench, and extract with ethyl acetate;

[0032] (2) Drying the extract, vacuum distillation, and silica gel column separation in sequence to obtain methyl acetylenone.

Embodiment 2

[0034] (1) Add acetophenone (the amount of acetophenone substance 10mmol, quality 1201.5mg, volume 1.166.5ml) to the methanol solution (20ml) of p-toluenesulfonyl hydrazide at one time, and react at 60°C under stirring conditions to A large amount of white solid appeared in the solution; the solid precipitate was washed with petroleum ether to obtain p-toluenesulfonyl hydrazone.

Embodiment 3

[0036] (1) Under argon atmosphere and stirring conditions, mix 0.2mmol methyl acetylenone, 0.4mmol p-toluenesulfonylhydrazone, 0.02mmol copper hydroxide and 1.0mmol lithium methoxide, add 4mL solvent toluene and 3.6 μL of water to obtain a reaction solution, and raise the temperature to 100°C for 12 to 24 hours;

[0037] (2) After the reaction is finished, remove insoluble solids by filtration, use a rotary evaporator for vacuum distillation, pressure 150hPa, water bath temperature 40°C, evaporation time 18-22min; use chromatography column chromatography separation technology for concentration and separation, silica gel 200-300 mesh , Developing agent polar ethyl acetate / petroleum ether=1 / 49 (v / v), to obtain the target product 4,4-disubstituted cyclopentenone.

[0038] The obtained target product was detected, and the results were as follows: figure 1 , 2 as shown, figure 1 for 4-methyl-4-phenylcyclopentenone 1 H NMR spectrum, figure 2 for 4-methyl-4-phenylcyclopentenone...

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Abstract

The invention discloses a 4-methyl-4-phenylcyclopentenone compound and a preparation method thereof. The preparation method comprise the following steps: under an inert gas atmosphere and stirring conditions, mixing 0.18-0.22 mmol of methyl ethynyl ketone, 0.38-0.42 mmol of p-toluenesulfonylhydrazone, 0.018-0.022 mmol of copper hydroxide, and 0.8-1.2 mmol of lithium methoxide, adding 3-5 mL of toluene and 3.5-3.8 [mu]L of water into the mixed solution to obtain a reaction solution, performing heating to 95-105 DEG C and carrying out a reaction for 12-24 h, removing an insoluble solid by filtration after the reaction is completed, and performing vacuum distillation and concentration separation on the obtained solution to obtain the target product 4,4-disubstituted cyclopentenone. The preparation method has simple required process conditions and mild reaction conditions, 4,4-disubstituted cyclopentenone derivatives can be effectively obtained, and the reaction has relatively good substrate applicability and functional group tolerance. At the same time, the carbon-carbon triple bond insertion cleavage method is used for the first time to prepare 4-methyl-4-phenylcyclopentenone.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis methodology, and in particular relates to a 4-methyl-4-phenylcyclopentenone compound and a preparation method thereof. Background technique [0002] The research on the activation reaction of carbon-carbon triple bond has a long history, which can be traced back to the early nineteenth century. Most of the early studies focused on the hydration of alkynes to ketones and the addition of triple bonds. Later, a variety of catalytic systems emerged, such as [Pd]-catalyzed Wacker oxidation to give o-diketones. Cyclization reactions of triple bonds (such as click chemistry) are widely used in medicine, materials, supramolecular chemistry, polymerization and biotechnology. In addition, the Sonogashira coupling reaction of terminal alkynes can construct carbon-carbon single bonds between unsaturated carbons. [0003] The scission reaction of carbon-carbon bond has a very wide application in o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45C07C49/683
CPCC07C45/45C07C303/40C07C2601/10C07C49/207C07C49/683C07C311/49
Inventor 姜耀甲荣家信李昊文吴荣
Owner NANJING UNIV OF TECH
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