Gamma-hydroxy ketone derivatives and a synthesis method thereof

A synthetic method and technology of hydroxy ketones, applied in the field of γ-hydroxy ketone derivatives, achieving the effects of mild reaction conditions, easy availability of raw materials, and high atom economy

Active Publication Date: 2019-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of halides as radical precursors to generate free radicals for the oxyalkylation of alkenes has rarely been reported.
At present, there are two main reports, one using visible light catalysis and the other using transi

Method used

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  • Gamma-hydroxy ketone derivatives and a synthesis method thereof
  • Gamma-hydroxy ketone derivatives and a synthesis method thereof
  • Gamma-hydroxy ketone derivatives and a synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] The specific process is: in the glove box, take p-methylstyrene 2a (35mg, 0.3mmol), Ru(bpy) 3 Cl 2 ·6H 2 O (4 mg, 0.006 mmol), α-bromoacetophenone 3a (120 mg, 0.6 mmol), NaHCO 3 (25mg, 0.3mmol) was added to a 25mL tube with a branch, and acetonitrile (3mL) and water (18mg, 0.3mmol) were added under a nitrogen atmosphere and reacted at room temperature for 24h under the irradiation of a 26W white CFL lamp. After the reaction was complete, the solvent was removed by rotary evaporation under reduced pressure, and then column chromatography (petroleum ether (60-90 ℃) / ethyl acetate: 20:1, v / v) obtained a light yellow liquid product 1a (53 mg, yield 70 %). The target product was confirmed by NMR and high-resolution mass spectrometry.

Embodiment 2

[0032]

[0033] The specific process is: weigh 1a (76mg, 0.3mmol) in the glove box, add sodium azide (20mg, 0.3mmol) into a 25mL reaction tube with a branch, and 2 Under protection, 3 mL of 1,4-dioxane and boron trifluoride diethyl ether (55 mg, 0.39 mmol) were added, and reacted at 90° C. for 4 h. The solvent was spun off, column chromatography: PE(60-90°C) / EA=10 / 1, v / v. The pale yellow liquid 4a (17 mg, yield 20%) was obtained. The target product was confirmed by NMR and high-resolution mass spectrometry.

[0034] Typical Compound Characterization Data

[0035] 4-Hydroxy-1,4-diphenyl-1-butanone derivative (1a), pale yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ8.02–7.85(m,2H),7.58–7.48(m,1H),7.42(dd,J=10.6,4.7Hz, 2H),7.25(d,J=8.0Hz,2H),7.14(d ,J=7.9Hz,2H),4.77(t,J=6.3Hz,1H),3.08(t,J=7.0Hz,2H),2.56(s,1H),2.33(s,3H),2.24– 2.09(m,2H). 13 C NMR (100MHz, CDCl 3 )δ200.7(s), 141.5(s), 137.3(s), 136.9(s), 133.2(s), 129.3(s), 128.7(s), 128.2(s), 125.8(s), 73.5( s), 34.9(s), 3...

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Abstract

The invention discloses gamma-hydroxy ketone derivatives and a synthesis method thereof. Styrene adopted as a raw material and alpha-bromoacetophenone are subjected to a coupling reaction under the action of a ruthenium complex and illumination to synthesize a series of gamma-hydroxy ketone derivatives with different structures. The derivatives can be further converted into functional products. The method has the advantages of easily available raw materials, simple operation, mild reaction conditions, and diversified functional groups.

Description

technical field [0001] The invention relates to a method for preparing a gamma-hydroxy ketone derivative by visible light catalysis. Using styrene, which is easy to prepare, has a wide range of sources and is cheap, as a raw material, under the action of ruthenium complexes and under light conditions, the hydroxyalkylation reaction of alkenes is realized to generate γ-hydroxyketones in one step. Compared with the existing synthetic method of γ-hydroxy ketone, the present invention has easy-to-obtain raw materials, simple operation, mild reaction conditions, and environmental friendliness; and utilizes light energy to realize the conversion of organic matter without adding any oxidizing agent or reducing agent, and has atomic High economical characteristics. Background technique [0002] Visible light is an inexpensive and abundant natural resource. Chemists are currently widely interested in how to efficiently use visible light to realize the conversion of organic compound...

Claims

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Application Information

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IPC IPC(8): C07C45/68C07C49/83C07C247/10
Inventor 汪全南余正坤
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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