New epoxidation method of 2-benzylidene-1,3-indan diketone double bond

A technology of benzylidene and indandione, applied in the field of 2-benzylidene-1, can solve the problems of inability to synthesize epoxidation products, large damage to substrates, strong oxidation performance of hydrogen peroxide, etc., and achieves good effects , the effect of simple operation and high product yield

Inactive Publication Date: 2013-10-09
YANGZHOU UNIV
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Problems solved by technology

[0003] Before the present invention, the current relatively mature double bond epoxidation method used hydrogen peroxide as an epoxidation reagent, but the disadvantage of this method is that the oxidation performance of hydrogen peroxide is too strong and the damage to the substrate is relatively large, while the highly conjugated double bond Epoxidized products cannot be synthesized by this method

Method used

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  • New epoxidation method of 2-benzylidene-1,3-indan diketone double bond
  • New epoxidation method of 2-benzylidene-1,3-indan diketone double bond
  • New epoxidation method of 2-benzylidene-1,3-indan diketone double bond

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Embodiment Construction

[0013] 1. Reaction steps (taking the epoxidation of 2-phenylmethylene-1,3-indandione as an example):

[0014] Add 1mmol of 2-benzylidene-1,3-indandione, 0.25mmol of phenylisothiocyanate, 0.25mmol of thiazolium salt catalyst, 0.25mmol of triethylamine and 10mL of ethanol into a 50mL round bottom flask as solvent , stirred at room temperature for 30 min, evaporated most of the solvent residue and separated the product by thin layer chromatography (ethyl acetate:petroleum ether=1:4), product 227mg.

[0015] In the thin layer chromatography adopted, a mixture of cyclohexane and ethyl acetate was used as an eluent, and the mixing volume ratio of cyclohexane and ethyl acetate was 4:1.

[0016] Different epoxidized products can be obtained by substituting different substituted 2-benzylidene-1,3-indanediones for 2-benzylidene-1,3-indanediones.

[0017] General reaction formula of the present invention is:

[0018]

[0019] 2. Product identification:

[0020] Adopting different s...

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Abstract

The invention relates to a new epoxidation method of 2-benzylidene-1,3-indan diketone double bond. The method comprises the following steps of: adding 2-benzylidene-1,3-indan diketone, phenyl isothiocyanate, 3-benzyl-5-(2-ethoxy)-4-methyl thiazole chlorate and triethylamine in a molar ratio of 1:0.25:0.25:0.25 into a reaction container containing a certain amount of ethanol, stirring at room temperature until the reaction is ended, steaming and removing the ethanol, and carrying out thin layer chromatography separation on residues to obtain the epoxidized product of 2-benzylidene-1,3-indan diketone double bond. By adopting the method, the defects that substrates are destroyed due to strong oxidation property of hydrogen peroxide in the double-bond epoxidation method by using hydrogen peroxide as the epoxidation reagent and epoxidation products cannot be synthesized from highly conjugated double bonds by the method are overcome. The method is simple to operate, low in energy consumption and high in productivity, and heating is not required.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a new method for epoxidizing the double bond of 2-benzylidene-1,3-indandione. Background technique [0002] The epoxidation of double bonds is one of the most important organic reactions in organic synthesis, and the epoxidized products of double bonds have become important molecular building blocks in organic synthesis because of their high activity. Therefore, the epoxidation method of double bond has always been a hotspot in the research of organic reactions. [0003] Before the present invention, the current relatively mature double bond epoxidation method used hydrogen peroxide as an epoxidation reagent, but the disadvantage of this method is that the oxidation performance of hydrogen peroxide is too strong and the damage to the substrate is relatively large, while the highly conjugated double bond Epoxidized products cannot be synthesized by this met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/32C07D301/03C07D303/08
Inventor 景崤壁冯浩
Owner YANGZHOU UNIV
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