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One-step synthesis method for polysubstituted 2-cyclohexen-1-one

A synthetic method and multi-substitution technology, applied in the field of biomedicine, can solve the problems of limited types of cyclohex-2-enone derivatives, reaction failure, corrosion, etc., and achieve a wide range of substrates, easy operation, and cheap raw materials Effect

Active Publication Date: 2020-11-24
GUANGDONG UNIV OF PETROCHEMICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this one-step reaction greatly simplifies the synthesis steps, it needs to consume precious metal rhodium catalyst and stoichiometric silver, and the corrosion of acetone to the sealing ring of the equipment under high temperature and high pressure reaction conditions often leads to reaction failure.
This method generally involves two reactants, and the types of cyclohex-2-enone derivatives synthesized are limited, and the applicable range of substrates is also narrow.

Method used

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  • One-step synthesis method for polysubstituted 2-cyclohexen-1-one
  • One-step synthesis method for polysubstituted 2-cyclohexen-1-one
  • One-step synthesis method for polysubstituted 2-cyclohexen-1-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of 5-Benzyl-3-phenylcyclohex-2-enone

[0038]

[0039] Add phenylacetylene (102mg, 1.0mmol), acetophenone (144mg, 1.2mmol), sodium tert-butoxide (144mg, 1.5mmol), and dimethyl sulfoxide (3mL) into the reaction flask in sequence, and heat up to 100°C while stirring , keep stirring for 30 minutes. Then add ethyl acetoacetate (156mg, 1.2mmol) in reaction bottle, after insulation reaction for 5 hours, TLC spot plate, raw material point disappears, promptly reacts completely, stops stirring. Extract twice with ethyl acetate and distilled water, then wash with saturated NaCl solution, combine the organic phases, dry the organic phase with anhydrous magnesium sulfate, filter to remove magnesium sulfate, remove the solvent ethyl acetate by rotary evaporation, and purify by column chromatography to obtain colorless Oily 5-benzyl-3-phenylcyclohex-2-enone (217 mg, 83% yield). product by 1 H NMR and 13 C NMR confirmed the following: 1 HNMR (400MHz, CDCl 3 ), δ×...

Embodiment 2

[0041] Preparation of 5-Benzyl-3-phenylcyclohex-2-enone

[0042]

[0043]Phenylacetylene (102mg, 1.0mmol), acetophenone (132mg, 1.1mmol), potassium tert-butoxide (134mg, 1.2mmol), and dimethyl sulfoxide (3mL) were sequentially added to the reaction flask, and the temperature was raised to 110°C under stirring. , keep stirring for 40 minutes. Then add ethyl acetoacetate (143mg, 1.1mmol) in reaction bottle, after insulation reaction for 6 hours, TLC plate, raw material spot disappears, promptly reacts completely, stops stirring. Distilled water was added, extracted twice with ethyl acetate, and the organic phases were combined. Then wash with saturated NaCl solution, dry the organic phase with anhydrous magnesium sulfate, filter to remove magnesium sulfate, remove the solvent by rotary evaporation, and purify by column chromatography to obtain 5-benzyl-3-phenylcyclohex-2-ene as a colorless oil Ketone (212 mg, 81% yield). The product was identified by 1H NMR and 13C NMR as ...

Embodiment 3

[0045] Preparation of 4-benzyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one

[0046]

[0047] Add phenylacetylene (102mg, 1.0mmol), cyclohexanone (118mg, 1.2mmol), sodium tert-butoxide (144mg, 1.5mmol), and DMSO (3mL) into the reaction flask in turn, heat up to 100°C while stirring, and keep stirring 30 minutes. Then add ethyl acetoacetate (156mg, 1.2mmol) in the reaction bottle, after insulation reaction for 7 hours, TLC spot plate, raw material spot disappears, promptly reaction is complete, stop stirring. Distilled water was added, extracted twice with ethyl acetate, and the organic phases were combined. Then wash with saturated NaCl solution, dry the organic phase with anhydrous magnesium sulfate, filter to remove magnesium sulfate, remove the solvent ethyl acetate by rotary evaporation, and purify by column chromatography to obtain colorless oil 4-benzyl-4,4a,5,6 , 7,8-Hexahydronaphthalene-2(3H)-one (206 mg, 86% yield). product by 1 H NMR and 13 C NMR confirmed the ...

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Abstract

The invention relates to the field of biological medicines, and discloses a one-step synthesis method of polysubstituted 2-cyclohexen-1-one. The method comprises the following step: with terminal alkyne, ketone and ethyl acetoacetate as reaction raw materials, conducting a reaction in an aprotic polar solvent in the presence of strong alkali to obtain polysubstituted 2-cyclohexen-1-one. Accordingto the method, the adopted raw materials are cheap, a noble metal catalyst is not needed in reaction process, operation is simple and convenient, time is short, the range of applicable substrates is wide, and substituent groups at the positions 3, 4 and 5 of 2-cyclohexen-1-one can be freely adjusted through the types of alkyne and ketone.

Description

technical field [0001] The invention relates to the field of biomedicine, more specifically, to a one-step synthesis method of multi-substituted cyclohex-2-enones. Background technique [0002] The preparation of cyclohex-2-enone derivatives is an important means of constructing carbocyclic skeletons. This type of compound also plays an important role in the synthesis of some physiologically active natural products and drug molecules. It is also the preparation of some special structures Phenols, such as raw materials for meta-substituted phenols (Liang Y.; Song S.; Ai L.; Lia X.; Jiao N. Green Chem., 2016, 18, 6462–6467). Cyclohex-2-enone derivatives can be prepared from 3-hydroxycyclohexanone dicarboxylate by dehydration and decarboxylation in a mixed solvent of concentrated hydrochloric acid and glacial acetic acid for a long time (Kmatchi, S.; Mohan, S. ; Gomathi, R. et al. K. Indian Journal of Chemistry: Section B, 2009, 48B, 553-562). However, the raw materials of th...

Claims

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Application Information

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IPC IPC(8): C07C49/657C07C49/67C07C49/697C07C49/753C07C45/74
CPCC07C45/74C07C2601/16C07C2602/28C07C2601/02C07C49/657C07C49/67C07C49/697C07C49/753
Inventor 蒋达洪张志华李磊孙婧王煦张桂禧鲍琳
Owner GUANGDONG UNIV OF PETROCHEMICAL TECH
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