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A kind of method of synthesizing α-alkyl ketone

A synthesis method and technology of alkyl ketones are applied in the field of synthesis of α-alkyl ketones to achieve the effect of broad development prospects

Inactive Publication Date: 2018-02-13
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the use of these known transition metal catalysts to catalyze the α-alkylation of ketones still requires the use of N 2 Carry out under the protection of, and use a large amount of inorganic strong base (especially KOH)

Method used

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  • A kind of method of synthesizing α-alkyl ketone
  • A kind of method of synthesizing α-alkyl ketone
  • A kind of method of synthesizing α-alkyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: 1,3-diphenyl-1-propanone

[0026] 1,3-diphenylpropan-1-one

[0027]

[0028] Acetophenone (120mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), benzyl alcohol (120mg, 1.1mmol) and tert-amyl alcohol ( 1ml) into a 5mL round bottom flask in turn. The reaction mixture was refluxed in air for 6 hours and then cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 92%

[0029] 1 H NMR (500MHz, CDCl 3 )δ7.96(d, J=7.2Hz, 2H, ArH), 7.55(t, J=6.9Hz, 1H, ArH), 7.45(t, J=6.9Hz, 2H, ArH), 7.34-7.23(m ,4H,ArH),7.20(t,J=6.7Hz,1H,ArH),3.30(t,J=7.3Hz,2H,CH 2 ), 3.07(t, J=7.3Hz, 2H, CH 2 ); 13 C NMR (125MHz, CDCl 3 )δ 199.2, 141.3, 136.9, 133.0, 128.6, 128.5, 128.4, 128.0, 126.1, 40.4, 30.1.

Embodiment 2

[0030] Example 2: 3-(4-methylphenyl)-1-phenyl-1-propanone

[0031] 1-phenyl-3-p-tolylpropan-1-one

[0032]

[0033] Acetophenone (120mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), 4-methylbenzyl alcohol (135mg, 1.1mmol) and Tert-amyl alcohol (1 mL) was sequentially added to a 5 mL round bottom flask. The reaction mixture was refluxed in air for 6 hours and then cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 88%

[0034] 1 H NMR (500MHz, CDCl 3 )δ7.96(d, J=6.4Hz, 2H, ArH), 7.55(t, J=7.1Hz, 1H, ArH), 7.45(t, J=7.4Hz, 2H, ArH), 7.21-7.05(m ,4H,ArH),3.28(t,J=7.2Hz,2H,CH 2 ), 3.03(t, J=7.2Hz, 2H, CH 2 ),2.32(s,3H,CH 3 ); 13 C NMR (125MHz, CDCl 3 )δ 199.3, 138.2, 136.9, 135.6, 133.0, 129.2, 128.6, 128.3, 128.0, 40.6, 29.7, 21.0.

Embodiment 3

[0035] Example 3: 3-(4-methoxyphenyl)-1-phenyl-1-propanone

[0036]3-(4-methoxyphenyl)-1-phenylpropan-1-one

[0037]

[0038] Acetophenone (120mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol, 0.1equiv.), 4-methoxybenzyl alcohol (152mg, 1.1mmol ) and tert-amyl alcohol (1 mL) were sequentially added to a 5 mL round bottom flask. The reaction mixture was refluxed in air for 6 hours and then cooled to room temperature. Rotary evaporation removes solvent, then obtains pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 90%

[0039] 1 H NMR (500MHz, CDCl 3 )δ7.96(d, J=7.5Hz, 2H, ArH), 7.55(t, J=7.1Hz, 1H, ArH), 7.45(t, J=7.4Hz, 2H, ArH), 7.17(d, J =8.0Hz,2H,ArH),6.84(d,J=8.0Hz,2H,ArH),3.79(s,3H,CH 3 )3.27(t, J=7.5Hz, 2H, CH 2 ), 3.01(t, J=7.5Hz, 2H, CH 2 ); 13 C NMR (125MHz, CDCl 3 )δ199.3, 157.9, 136.8, 133.3, 133.0, 129.3, 128.5, 128.0, 113.9, 55.2, 40.7, 29.2.

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Abstract

The invention discloses a method for synthesizing α-alkyl ketone. In the reaction vessel, add ketone, compound alcohol, iridium complex catalyst, base and solvent tert-amyl alcohol, after the reaction mixture is refluxed in the air for several hours, it is cooled to room temperature, the solvent is removed by rotary evaporation, and then separated by column to obtain target compound. The present invention uses a metal-organic bifunctional iridium complex, the reaction only needs to add 0.1 equivalent of carbonate, carried out in the air, and the reaction only needs 6 hours, showing obvious advantages; therefore, the reaction meets the requirements of The requirements of green chemistry have broad prospects for development.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing α-alkyl ketones. Background technique [0002] α-Alkyl ketones are a very important class of compounds, exhibiting a wide range of physiological and pharmacological activities. For example, such compounds are used as reversible ketoheterocyclic inhibitors of fatty acid amide hydrolase (OL-135), inhibitors of thyroid receptor coactivator binding, orally bioavailable phthalazinone bradykinin B1 receptors, body antagonists and 5-HT 7 receptor ligands, etc. (a) D. L. Boger, H. Miyauchi, W. Du, C. Hardouin, R. A. Fecik, H. Cheng, I. Hwang, M. P. Hedrick, D. Leung, O. Acevedo, C. R. W. W.L.Jorgensen, B.F.Cravatt, J.Med.Chem.2005,48,1849-1856; b) J.Y.Hwang, L.A.Arnold, F.Zhu, A.Kosinski, T.J.Mangano, V.Setola, B.L.Roth, R.K.Guy, J. .Med.Chem.2009, 52, 3892-3901; c) K.Biswas, T.A.N.Peterkin, M.C.Bryan, L.Arik, S.G.Lehto, H.Su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/04C07C45/71C07C49/782C07C49/84C07C49/813C07C49/80C07C49/76C07C49/792C07C49/788C07C49/67C07C49/213C07C49/313C07D307/46C07F17/02C07D333/22
Inventor 李峰马娟陆磊
Owner NANJING UNIV OF SCI & TECH