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Method for synthesizing alpha-alkyl ketone

A technology of alkyl ketone and alkyl group, which is applied in the field of synthesis of α-alkyl ketone and achieves the effect of broad development prospects

Inactive Publication Date: 2016-03-30
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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  • Method for synthesizing alpha-alkyl ketone
  • Method for synthesizing alpha-alkyl ketone
  • Method for synthesizing alpha-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 HNMR (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 CNMR (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 HNMR (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 CNMR (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 HNMR (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 CNMR (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 alpha-alkyl ketone. The method comprises the following steps: adding ketone, a compound alcohol, an iridium complex catalyst, an alkali and a solvent tert-amyl alcohol in a reaction container, carrying out a refluxing reaction on the above obtained reaction mixture in air for several hours, cooling the obtained reaction product to room temperature, carrying out rotary evaporation to remove the solvent, and carrying out column separation to obtain the target compound. The meta-organic bifunctional iridium complex is used, only 0.1 equivalent carbonate is added in the reaction process, and the reaction is carried in air for 6h, so obvious advantages are displayed; and the reaction accords with green chemistry requirements, and has wide development prospect.

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