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Method for preparing alpha-acyloxy ketone compound

A technology for acyloxyketones and compounds, which is applied in the field of preparation of α-acyloxyketone compounds, can solve the problems of restricting wide application, and achieve the effects of high atom economy, high yield and wide substrate adaptability

Active Publication Date: 2017-03-22
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned synthetic methods still either use some toxic metal catalysts or use dangerous peroxides as oxidants, which limits their wide application in the fields of organic synthesis and medicinal chemistry. Therefore, to study a simple , safe and efficient synthetic methods are urgently needed

Method used

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  • Method for preparing alpha-acyloxy ketone compound
  • Method for preparing alpha-acyloxy ketone compound
  • Method for preparing alpha-acyloxy ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] At room temperature, 1-phenylpropanol (0.136 g, 1 mmol), benzoic acid (0.183 g, 1.5 mmol), NBS (0.356 g, 2 mmol) and 1,4-dioxo Hexacyclic (2 mL). Stir at 60°C for 1 hour, then add DBU (0.304 g, 2 mmol) and continue the reaction for 2 hours (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product α-acyloxyketone compound (yellow solid 0.251 g, yield 99%).

[0042] 1 H NMR (CDCl 3 , 400 MHz, ppm): δ8.12 (d, J = 7.1 Hz, 2H), 8.03 (d, J =7.1 Hz, 2H), 7.63-7.58 (m, 2H), 7.53-7.45 (m, 4H), 6.24 (q, J = 7.0 Hz, 3H), 1.70 (d, J = 7.0 Hz, 3H); 13 C NMR (CDCl 3 , 100 MHz, ppm): δ196.7, 166.0, 134.5,133.6, 133.3, 129.9, 129.5, 128.8, 128.5, 128.4, 71.9, 17.2; HRMS calc. 16 h 14 o 3 Na (M+Na) + , 277.0841; found, 277.084...

Embodiment 2

[0044]

[0045] At room temperature, 4-methyl-1-phenylpropanol (0.15 g, 1 mmol), benzoic acid (0.183 g, 1.5 mmol), NBS (0.356 g, 2 mmol) and 1 , 4-dioxane (2 mL). Stir at 60°C for 1 hour, then add DBU (0.304 g, 2 mmol) and continue the reaction for 4 hours (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product α-acyloxyketone compound (white solid 0.239g, yield 89%).

[0046] 1 H NMR (CDCl 3 , 400 MHz, ppm): δ8.11 (d, J = 7.0 Hz, 2H), 7.93 (d, J =8.2 Hz, 2H), 7.60 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.9 Hz, 2H), 7.31 (d, J =8.0 Hz,2H), 6.22 (q, J = 7.0 Hz, 1H), 2.44 (s, 3H), 1.69 (d, J = 7.0 Hz, 3H); 13 C NMR (CDCl 3 for C 17 h 16 o 3 Na (M+Na) + , 291.0997; found, 291.0999.

Embodiment 3

[0048]

[0049] At room temperature, 1-phenylethanol (0.122 g, 1 mmol), benzoic acid (0.183 g, 1.5 mmol), NBS (0.356 g, 2 mmol) and 1,4-dioxane were sequentially added to a 50 mL round bottom flask ring (2 mL). Stir at 60°C for 1 hour, then add DBU (0.304 g, 2 mmol) and continue the reaction for 4 hours (reaction detected by TLC). Then, the reaction was stopped and concentrated under reduced pressure to obtain a crude product. Finally, it was washed with a mixed eluent of petroleum ether and ethyl acetate, and flash column chromatography (silica gel column) obtained the corresponding product α-acyloxyketone compound (white solid 0.211g, yield 88%).

[0050] 1 H NMR (CDCl 3 , 400 MHz, ppm): δ8.17 (d, J = 7.1 Hz, 2H), 8.00 (d, J =7.1 Hz, 2H), 7.66-7.61 (m, 2H), 7.56-7.48 (m, 4H), 5.61 (s, 2H); 13 C NMR (CDCl 3 , 100 MHz, ppm): δ192.3, 166.0, 134.4, 133.9, 133.3, 130.0, 128.9,128.5, 127.9, 66.5; HRMS calc. for C 15 h 12 o 3 Na (M+Na) + , 263.0684; found, 263.0685....

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Abstract

The invention discloses a method for preparing an alpha-acyloxy ketone compound. According to the invention, simple and easily available alcohol and carboxylic acid are taken as the raw materials, under mediation of NBS(N-bromo-succinimide) and DBU(1,8-diazabicyclo(5.4.0)undec-7-alkene), the alpha-acyloxy ketone is prepared by a one-pot reaction. The method has the advantages of mild reaction condition, simple and easily available raw materials, wide substrate adaptation scope, no requirement of rigorous reaction conditions such as any metal catalyst, peroxy compounds, low or high temperature and water-free and oxygen-free conditions, metal pollution is avoided; and the method also has the advantages of stable technical condition, simple and safe operation, and easy purifying of the product.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, and relates to a preparation method of α-acyloxyketone compounds, in particular to a method for directly synthesizing α-acyloxyketone compounds by reacting alcohol and carboxylic acid mediated by NBS / DBU. Background technique [0002] α-acyloxyketones (α-acyloxyketones) compounds are of great significance in practical applications such as chemical research, chemical engineering, functional materials and drug development. The structural fragments of α-acyloxyketone compounds widely exist in natural products and often serve as the key structural skeletons of physiologically active molecules and drug molecules. α-Acyloxyketones are important scaffolds in organic complexes. Studies have shown that substances containing this structural fragment have many biological activities, such as antibacterial, anti-inflammatory, anti-tuberculosis, anti-convulsant, anti-tumor, etc. [0003] The tradit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/00C07C69/78C07C69/76C07C69/92C07C201/12C07C205/57C07C69/612C07C69/14C07C69/24C07C69/606C07C69/56C07B41/12
CPCC07B41/12C07C67/00C07C201/12C07C69/78C07C69/76C07C69/92C07C205/57C07C69/612C07C69/14C07C69/24C07C69/606C07C69/56
Inventor 王桦魏伟朱明慧崔环环
Owner QUFU NORMAL UNIV
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