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Synthesis method for beta-hydroxy-ketone compound

A synthetic method and compound technology, applied in the field of synthesizing β-hydroxy ketone compounds, can solve the problems of unfavorable practical application and restriction of wide application, and achieve the effects of good substrate adaptability, simple reaction operation, and avoiding residues

Inactive Publication Date: 2015-10-28
上海汉亭化学有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method inevitably produces by-products, such as its own condensation reaction, polycondensation reaction, Michael addition, etc., which is not conducive to practical application.
In recent years, some other methods for synthesizing compounds containing β-hydroxy ketone structural units have also been reported, but the problem of using metal catalysts cannot be avoided in these synthetic methods, which greatly limits the wide application of these methods in the field of medicine

Method used

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  • Synthesis method for beta-hydroxy-ketone compound
  • Synthesis method for beta-hydroxy-ketone compound
  • Synthesis method for beta-hydroxy-ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] 1-Phenylvinyl acetate (81mg, 0.5mmol), isopropanol (2mL, 26.2mmol) and tert-butyl hydroperoxide (257.2mg, 2.0mmol, 70% aqueous solution) were added to the flask, at 100 °C for 10 hours. After the reaction was detected by TLC, it was separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 6:1) to obtain 3-hydroxyl-3-methyl-1-phenylbutan-1-one (Compound 1) 56.1 mg, yield 63%.

[0036] Product characterization: pale yellow liquid; 1 H NMR (500MHz, CDCl 3 )δ7.96(dt,J=8.5,1.5Hz,2H),7.63–7.56(m,1H),7.51–7.46(m,2H),3.16(s,2H),1.35(s,6H).13C NMR (125MHz, CDCl 3 )δ200.7, 136.5, 132.5, 127.7, 127.1, 68.9, 47.7, 28.6.

Embodiment 2

[0038]

[0039] 1-(p-Methylphenyl) vinyl acetate (88 mg, 0.5 mmol), isopropanol (2 mL, 26.2 mmol) and tert-butyl hydroperoxide (257.2 mg, 2.0 mmol, 70% aqueous solution) were added to In the flask, the reaction was carried out at 100° C. for 12 hours. After the reaction was detected by TLC, it was separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 6:1) to obtain 3-hydroxyl-3-methyl-1-p-methylphenylbutane- 1-ketone (compound 2) 51 mg, yield 53%.

[0040] Product characterization: pale yellow liquid; 1 H NMR (500MHz, CDCl 3 )δ7.85(d, J=8.2Hz, 2H), 7.27(d, J=8.6Hz, 2H), 3.12(s, 2H), 2.42(s, 3H), 1.34(s, 6H). 13 C NMR (125MHz, CDCl 3 )δ201.5, 144.6, 134.8, 129.4, 128.2, 69.9, 48.4, 29.6, 21.7.

Embodiment 3

[0042]

[0043] 1-(4-Chlorophenyl)vinyl acetate (98 mg, 0.5 mmol), isopropanol (2 mL, 26.2 mmol) and tert-butyl hydroperoxide (257.2 mg, 2.0 mmol, 70% aqueous solution) were added to In the flask, the reaction was carried out at 100° C. for 6 hours. After the reaction was detected by TLC, it was separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 6:1) to obtain 3-hydroxyl-1-(3-methoxyphenyl)-3-methanol Butan-1-one (compound 3) 61 mg, yield 58%.

[0044] Product characterization: pale yellow liquid; 1 H NMR (500MHz, CDCl 3 )δ7.92–7.87(m,2H),7.48–7.42(m,2H),3.91(s,1H),3.12(s,2H),1.35(s,6H). 13 C NMR (125MHz, CDCl 3 )δ200.3, 140.1, 135.6, 129.5, 129.0, 69.8, 48.7, 29.5.

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Abstract

The invention provides a synthesis method for a beta-hydroxy-ketone compound shown in a formula (III). The method comprises the steps that substitute vinyl acetate shown in a formula (I), a substitute alcohol compound shown in a formula (II) and an oxidizing agent are mixed to obtain reaction liquid, and the reaction liquid reacts for 2-12 hours at the temperature of 20 DEG C-120 DEG C, and then is treated to obtain the beta-hydroxy-ketone compound. The method is safe and environmentally friendly, and is a new path for synthesizing the beta-hydroxy-ketone compound containing various substituents, the substrate adaptability is good, and the reaction operation is easy.

Description

(1) Technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing β-hydroxy ketones. (2) Background technology [0002] β-Hydroxyketone is a very important structural unit, which widely exists in nature and drug molecules. For example, the compound erythromycin A is a secondary metabolite produced by Streptomyces erythromycin, which is similar to penicillin in medicine and can be used as an antibiotic for some patients who are allergic to penicillin; such as the compound tacromol Division, is an immunosuppressive drug, can prevent rejection in organ transplantation. Therefore, β-hydroxyketones, as versatile structural units, have attracted extensive attention in the field of chemical research. [0003] In general, the main synthetic method of β-hydroxyketones is through the aldol reaction. This method is to convert a certain carbonyl compound into the corresponding enolate under the action of a strong ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/82C07C49/84C07C49/83C07C49/17C07C45/45C07C45/51
CPCC07C45/45C07C45/515C07C2601/14C07C49/82C07C49/84C07C49/83C07C49/17
Inventor 李小青唐裕才许响生
Owner 上海汉亭化学有限公司
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