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Synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives

A synthesis method and technology of derivatives, applied in chemical instruments and methods, preparation of organic compounds, condensation preparation of carbonyl compounds, etc., can solve the problem that ortho-bifunctional aromatics are not easy to obtain, and achieve high reaction yield and simple operation , good effect of atom economy

Inactive Publication Date: 2019-01-11
JILIN INST OF CHEM TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, ortho-difunctionalized arenes are not usually readily available and complex prefunctionalization methods are often required to obtain these arenes

Method used

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  • Synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives
  • Synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives
  • Synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives

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Embodiment 1～16

[0029] Add benzoylformic acid (0.2mmol), alkyne compound (0.2mmol), pentamethylcyclopentadiene iridium dichloride (0.02mmol), copper acetate (0.04 mmol), silver hexafluoroantimonate (0.02mmol), three (3-methoxyphenyl) phosphine (0.02mmol) and organic solvent 1ml, mixed and stirred evenly, after the reaction was completed according to the reaction conditions in Table 2, cooled, pumped Filter, mix the sample with silica gel, and purify by column chromatography to obtain the corresponding 2,3-diphenyl-1H-inden-1-one derivative (I).

[0030] The raw material ratio of table 1 embodiment 1~16

[0031]

[0032] The reaction conditions and reaction result of table 2 embodiment 1~16

[0033]

[0034] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, n-Bu is n-butyl, and 1-naphthyl is 1-substituted naphthyl. R except Ι-2, Ι-12 2 Except for ortho substitution, R 2 are all substituted for the paraposition.

[0035] The structure confirmation data of...

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Abstract

The invention discloses a synthesis method for 2,3-diphenyl-1H-indene-1-one derivatives. The synthesis method comprises the steps of: adding benzoyl formic acid, a diphenyl acetylene compound, pentamethyl cyclopentadiene dichloride iridium, copper acetate, silver hexafluoroantimonate and a silver hexafluoroantimonate into an organic solvent; heating for reaction in the presence of air; and after the reaction, carrying out post-treatment to obtain the 2,3-diphenyl-1H-indene-1-one derivative. The method synthesizes the 2,3-diphenyl-1H-indene-1-one derivative in one step through simple and easilyavailable raw materials, so that the conversion efficiency is high and the atomic economical benefit is good. Meanwhile, the synthetic method is simple to operate, high in reaction yield and wide inprimer adaptability.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of 2,3-diphenyl-1H-inden-1-one derivatives. Background technique [0002] Indanones are useful intermediates in organic synthesis, and are also widely used in the fields of biology and materials. The traditional method for preparing indanone is to obtain it through Fried-Crafts cyclization synthesis method. This method requires the use of electron-rich aromatic reagents as starting materials, thus limiting the scope of the reaction. In addition, the reaction conditions are relatively harsh, and harmful by-products are often generated during the reaction. Transition metal-catalyzed ortho-difunctionalized arenes and alkyne cycloadditions were then used to prepare indanones. Starting materials are not limited to electron-rich aromatic compounds, and many electron-deficient compounds have been successfully used in these reactions. However, ortho-dif...

Claims

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Application Information

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IPC IPC(8): C07C45/48C07C49/67C07C49/755C07C49/697C07C67/343C07C69/76
CPCC07C45/48C07C67/343C07C2602/08C07C49/67C07C49/755C07C49/697C07C69/76
Inventor 于晓波
Owner JILIN INST OF CHEM TECH
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