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A kind of synthetic method of 1,4-butenediones

A synthetic method and technology of butenedione, applied in 1 field, can solve problems such as complex raw materials, harsh conditions, and metal participation, and achieve the effect of simple raw materials, mild reaction conditions, and no metal participation

Active Publication Date: 2015-10-28
山东博洛德生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problems of metal participation, complex raw materials and harsh conditions in the current method for synthesizing 1,4-butenediones, the present invention proposes a method for synthesizing 1,4-butenediones. The invention provides a method for synthesizing 1,4-butenediones with simple and easy-to-obtain raw materials, no metal participation, and mild reaction conditions

Method used

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  • A kind of synthetic method of 1,4-butenediones
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  • A kind of synthetic method of 1,4-butenediones

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Effect test

Embodiment 1

[0017]

[0018] 0.5mmol phenylacetylene, 10ml CH 3 CN was added to a 50ml reaction flask, and 1mmol Selectfluor and 1mmol phenol were added to the reaction flask twice with an interval of 2 hours. After the addition was completed, it was placed at 30°C and continued to stir for 20 hours. Then, two spoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate volume ratio of 10 :1 as eluent). The material was a yellow solid, 53% yield.

[0019] Characterization data: R f =0.48 (petroleum ether-EtOAc, 6:1); mp108-111°C; IR (neat, cm -1 )v: 1660 (C=O), 1620 (C=C); E: Z=12:1; 1 HNMR (CDCl 3 , 500MHz) δ: 8.07-8.05 (m, 2H), 8.07 (s, 1H), 7.65-7.61 (m, 2H), 7.54-7.51 (t, J=8Hz, 2H); 13 C NMR (CDCl 3 , 125MHz) δ: 189.8, 136.9, 135.1, 133.8, 128.86, 128.85; MS (EI, 70eV): ...

Embodiment 2

[0021]

[0022] 0.5mmol phenylacetylene, 10ml CH 3 Add CN to a 50ml reaction bottle, then add 1mmol Selectfluor and 1mmol phenol, after the addition is complete, place it at 30°C and stir for 24 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate volume ratio of 10 :1 as eluent). The material was a yellow solid, 35% yield.

Embodiment 3

[0024]

[0025] 0.5mmol phenylacetylene, 10ml CH 3 CN was added to a 50ml reaction flask, and 1mmol Selectfluor and 1mmol phenol were added to the reaction flask twice with an interval of 2 hours. After the addition was complete, it was placed at 25°C and continued to stir for 20 hours. Then, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the pure product was obtained by column chromatography separation (with petroleum ether / ethyl acetate volume ratio of 10 :1 as eluent). The material was a yellow solid, 48% yield.

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Abstract

The invention belongs to the technical field of organic compound synthesis, provides a method for synthesizing a 1,4-butene diketone compound and aims to solve the problems that metal participates, materials are complex and the conditions are harsh in the method for synthesizing the 1,4-butene diketone compound at present. The synthesizing method comprises the step of reacting for 12-48h at 25-80 DEG C by using substituted aryne and phenol as initial materials, using 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2] octane bi(tetrafluoroboric acid) salt (selectfluor) as an oxidant and using CH3CN as a solvent to prepare the 1,4-butene diketone compound. The invention provides a method for synthesizing the 1,4-butene diketone compound, which has the advantages that materials can be easily obtained, no metal participates and the reaction condition is moderate. The reaction formula is shown in the specification.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a method for synthesizing 1,4-butenedione compounds. Background technique [0002] In recent years, 1,4-butenediones have attracted much attention because they are key building blocks of steroid drugs, anticancer antibiotics and some natural products. Meanwhile, 1,4-butenediones are important organic intermediates, which can be used in cycloaddition, Michael addition and other reactions. [0003] The traditional method of synthesizing this class of compounds has the following disadvantages: (1) metals are required as catalysts (see L.Keith Woo et al. Catal Lett (2010) 137:8-15; Rai-Shung Liu et al. Chem. Eur.J.2014,20,1-6; Zhiyong Wang et al.Org.Lett.2013,15,2148-2151.Because metal generally has certain toxicity, can contaminate final product.Therefore this method is accepted by pharmaceutical industry Larger restrictions. (2) The raw materials are complex an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/45C07C45/36C07C49/796C07C49/813
CPCC07C45/28C07C45/45C07C49/796C07C49/813
Inventor 刘运奎吴德贵张剑
Owner 山东博洛德生物科技有限公司
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