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Method for preparing chalcone compound by catalyzing selective hydrogenation reduction of acetylenic ketone with Ti (III) complex

A technology for chalcones and catalyzing alkynones, which is used in organic compound/hydride/coordination complex catalysts, preparation of organic compounds, preparation of carbon-based compounds, etc., to achieve a wide range of biological activity and medicinal value, reaction products Single, mild reaction conditions for effect

Active Publication Date: 2021-09-24
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the shortcomings of a single titanocene catalyst ligand catalysis, to provide a method for preparing chalcones with mild conditions, simple operation, short reaction time, single reaction product, good substrate applicability and high efficiency

Method used

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  • Method for preparing chalcone compound by catalyzing selective hydrogenation reduction of acetylenic ketone with Ti (III) complex
  • Method for preparing chalcone compound by catalyzing selective hydrogenation reduction of acetylenic ketone with Ti (III) complex
  • Method for preparing chalcone compound by catalyzing selective hydrogenation reduction of acetylenic ketone with Ti (III) complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Preparation of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one of the following structural formula:

[0016]

[0017] Add 0.103g (0.75mmol) Et to 20mL Shrek in the glove box 3 NHCl, 40mg (2.5eq) zinc powder, 0.0045g (5%mol) Cp * 2 TiCl 2 , 3mL of dichloromethane, stirred and reacted at room temperature for 10 minutes to prepare a trivalent titanium system, and dissolved 1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-one in 2mL Dichloromethane was then added to the trivalent titanium system, reacted at room temperature for 6h, and the dichloromethane was removed by rotary evaporation, separated with a silica gel column (the eluent was a mixture of ethyl acetate and petroleum ether with a volume ratio of 1:400), (E)-1-(4-Methoxyphenyl)-3-phenylprop-2-en-1-one was obtained in 86% yield.

[0018] The resulting product is characterized by a 400MHz nuclear magnetic resonance spectrometer (JEOL), and the characterization data are: 1 H NMR (400MHz, CDCl 3 )δ8.20(d, J=8.8Hz, 2...

Embodiment 2

[0020] Preparation of (E)-1-(4-methoxyphenyl)-3-(p-tolyl)propyl-2-en-1-one of the following structural formula:

[0021]

[0022] In Example 1, the 1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-one used was used with equimolar 1-(4-methoxyphenyl)-3- (P-tolyl) prop-2-yne-1-ketone replacement, other steps are the same as in Example 1, to obtain (E)-1-(4-methoxyphenyl)-3-(p-tolyl)propyl- 2-en-1-one in 80% yield.

[0023] The resulting product is characterized by a 400MHz nuclear magnetic resonance spectrometer (JEOL), and the characterization data are: 1 H NMRδ8.04(d, J=8.9Hz, 2H), 7.79(d, J=15.6Hz, 1H), 7.59-7.47(m, 3H), 7.22(d, J=8.0Hz, 2H), 6.98( d,J=8.9Hz,2H),3.89(s,3H),2.39(s,3H); 13 C NMR (101MHz, Chloroform-d) δ187.8, 162.3, 143.0, 139.8, 131.3, 130.2, 129.7, 128.6, 127.4, 119.8, 112.8, 54.5, 20.5.

Embodiment 3

[0025] Preparation of (E)-3-(4-bromophenyl)-1-(4-methoxyphenyl)propyl-2-en-1-one of the following structure:

[0026]

[0027] In Example 1, the 1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-one used was mixed with equimolar 3-(4-bromophenyl)-1-(4 -Methoxyphenyl propane)-2-yn-1-ketone replacement, other steps are the same as in Example 1, to obtain (E)-3-(4-bromophenyl)-1-(4-methoxybenzene base) propyl-2-en-1-one in 88% yield.

[0028] The resulting product is characterized by a 400MHz nuclear magnetic resonance spectrometer (JEOL), and the characterization data are: 1 H NMR (400MHz, Chloroform-d) δ8.08-7.97 (m, 2H), 7.72 (d, J = 15.7Hz, 1H), 7.57-7.45 (m, 5H), 7.02-6.93 (m, 2H), 3.88(s,3H); 13 C NMR (101MHz, Chloroform-d) δ187.3, 162.5, 141.5, 133.0, 131.1, 129.8 (d, J=4.5Hz), 128.7, 123.5, 121.3, 112.9, 54.5.

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Abstract

The invention discloses a method for preparing a chalcone compound by catalyzing selective hydrogenation reduction of acetylenic ketone with a Ti(III) complex.The method comprises the following steps: taking pentamethyl titanocene dichloride as a catalyst, zinc powder as a reducing agent and triethylamine hydrochloride as a proton source, and carrying out free radical selective addition reaction on acetylenic ketone and the triethylamine hydrochloride under the protection of inert gas to generate the chalcone compound. The method is mild in reaction conditions, simple to operate, short in reaction time, single in reaction product and high in atom economy, and only the product needs to be subjected to simple column chromatography separation after the reaction is finished. The obtained chalcone compound has wide biological activity and medicinal value.

Description

technical field [0001] The invention belongs to the technical field of free radical catalysis, and in particular relates to a method for preparing chalcone compounds through the selective hydrogenation of acetylene ketones catalyzed by a Ti(III) complex. Background technique [0002] Compounds containing α,β-enone structural units not only widely exist in natural products, medicines, and fine chemicals, but also play a variety of important roles, such as reducing uric acid, antibacterial, anti-inflammatory, anti-allergic, anti-cancer, etc. Biological activity can be used as a marker for disease detection, etc. In addition, compounds containing α,β-enone structural units are also an important class of synthetic intermediates, which are widely involved in a variety of organic transformation processes: they can undergo Michael addition reactions with various nucleophiles, or they can be connected in series The important intermediate of the reaction can also participate in the ...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/62C07D333/22B01J31/22
CPCC07C45/62C07D333/22B01J31/2295B01J2231/32B01J2531/0225B01J2531/46C07C49/84Y02P20/584
Inventor 高子伟郭应应杨明明简亚军孙华明
Owner SHAANXI NORMAL UNIV
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