A kind of synthetic method of α-position cycloalkyl substituted ketone compound

A technology of ketone compounds and synthetic methods, which is applied in the direction of carbon-based compound preparation, organic compound preparation, chemical instruments and methods, etc., can solve the problems of low reactivity of enamine intermediates and affect practical value, etc., and achieve short reaction time , Improved atom economy, high effect of atom economy

Inactive Publication Date: 2020-12-01
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method is relatively effective, it requires the use of a stoichiometric strong base and generates by-product metal halides, which to some extent affects its practical value
Another classic way to achieve the α-alkylation of ketones is the stoxenamine reaction. The advantage of this reaction is that it can specifically obtain monosubstituted alkylated products, but the disadvantage is that the generated enamine intermediates have relatively low reactivity. Low, thus requiring highly reactive halohydrocarbons or electron-deficient alkenes as alkylating agents

Method used

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  • A kind of synthetic method of α-position cycloalkyl substituted ketone compound
  • A kind of synthetic method of α-position cycloalkyl substituted ketone compound
  • A kind of synthetic method of α-position cycloalkyl substituted ketone compound

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Effect test

Embodiment 1

[0012]

[0013] Add propiophenone (1a, 0.5mmol, 67mg), cyclohexane (2a, 5mL) and di-tert-butyl peroxide (2mmol, 380μL) into a 25mL pressure-resistant tube, vacuumize and fill with nitrogen, and then put the pressure-resistant tube Seal it and place it in a microwave reactor, and stir and react at 160° C. for 1 hour. After the reaction, the unreacted cyclohexane was recovered by distillation under reduced pressure, and the residue was separated through a silica gel column (petroleum ether / dichloromethane=6 / 1) to obtain a colorless oily product 3a (67 mg, 62%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ:0.95-1.11(m,2H),1.15(d,J=7.2Hz,3H),1.17-1.27(m,3H),1.63-1.68(m,3H),1.73-1.77(m,3H) ,3.33(quint,J=6.8Hz,1H),7.46-7.50(m,2H),7.55-7.57(m,1H),7.95-7.97(m,2H). 13 C NMR (100MHz, CDCl 3 )δ: 14.0, 26.3, 26.4, 26.5, 29.2, 32.1, 40.7, 46.1, 128.2, 128.6, 132.8, 137.5, 205.1. HRMS calcd for C 15 h 21 O:217.1587[M+H] + ,found: 217.1589. ...

Embodiment 2

[0015] Add propiophenone (1a, 0.5mmol, 67mg), cyclohexane (2a, 5mL) and di-tert-butyl peroxide (1mmol, 190μL) into a 25mL pressure-resistant tube, vacuumize and fill with nitrogen, and then put the pressure-resistant tube Seal it and place it in a microwave reactor, and stir and react at 140° C. for 1 hour. After the reaction, the unreacted cyclohexane was recovered by distillation under reduced pressure, and the residue was separated through a silica gel column (petroleum ether / dichloromethane=6 / 1) to obtain a colorless oily product 3a (28 mg, 26%).

Embodiment 3

[0017] Add propiophenone (1a, 0.5mmol, 67mg), cyclohexane (2a, 5mL) and di-tert-butyl peroxide (1mmol, 190μL) into a 25mL pressure-resistant tube, vacuumize and fill with nitrogen, and then put the pressure-resistant tube Seal it and place it in a microwave reactor, and stir and react at 160° C. for 1 hour. After the reaction, the unreacted cyclohexane was recovered by distillation under reduced pressure, and the residue was separated through a silica gel column (petroleum ether / dichloromethane=6 / 1) to obtain a colorless oily product 3a (37 mg, 34%).

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Abstract

The invention discloses a synthetic method for an Alpha-bit naphthenic-substituted ketone compound, and belongs to the technical field of the organic synthesis. The technical solution of the synthetic method comprises the following steps: mixing a ketone compound and naphthenic hydrocarbon or dissolving in an organic solvent, reacting in the existence of microwave radiation and a radical initiator in 140-170 DEG C of the temperature, to obtain a target product of the Alpha-bit naphthenic-substituted ketone compound. According to the synthetic method, the ketone compound and the simple naphthenic hydrocarbon are used as the raw materials, and the Alpha-bit naphthenic-substituted ketone compound is obtained by a cross dehydrogenation coupled reaction. The method has the advantages of cheap and simple raw materials, short reaction time, no metal catalysis, environmental protection and high atom economy, and is suitable for the industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing α-position cycloalkyl substituted ketone compounds. Background technique [0002] The α-alkylation of ketones is an important method to construct carbon-carbon bonds, and it is also one of the common methods for the synthesis of ketone derivatives. This kind of alkylation reaction is usually realized by using halogenated alkanes as alkylating agents under the action of strong base. Although this method is relatively effective, it requires the use of a stoichiometric strong base and produces metal halides as by-products, which to some extent affects its practical value. Another classic way to achieve α-alkylation of ketones is the stoxenamine reaction. The advantage of this reaction is that it can specifically obtain monosubstituted alkylated products, but the disadvantage is that the generated enamine intermediates have relatively ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/67C07C49/792C07C49/84C07C49/813C07C49/237C07B60/00
CPCC07B61/02C07C45/002C07C45/673C07C49/792C07C49/84C07C49/813C07C49/237
Inventor 张新迎王倩倩范学森王章欣
Owner HENAN NORMAL UNIV
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