Spiro [cyclopropane-1, 2'-indene]-1', 3'-diketone derivative and synthesis method thereof

A synthesis method and cyclopropane technology are applied in the fields of medicine, organic synthesis, and pesticide intermediates, which can solve the problems of complexity and low diastereoselectivity, and achieve the effects of high selectivity and yield, and good industrial application prospects.

Active Publication Date: 2021-08-17
HUBEI UNIV OF SCI & TECH
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  • Claims
  • Application Information

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Benefits of technology

This patented method allows for cheaply created chemicals that can be used safely at different stages during production or processing processes. It also has great potential applications due its ability to produce highly pure products with excellent properties such as enantiomeric excesses while minimizing unwanted side reactions like impurities from other reactants involved therein.

Problems solved by technology

The technical problem addressed in this patented text relating to improving chemical processes involving certain types of rings or other structures called chirality (the ability to rotate around their own axis) involves finding new ways to efficiently create these ring configurations without compromising on its original properties. This would be useful because it could lead to novel drugs that target specific areas within cells like cancerous tissue.

Method used

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  • Spiro [cyclopropane-1, 2'-indene]-1', 3'-diketone derivative and synthesis method thereof
  • Spiro [cyclopropane-1, 2'-indene]-1', 3'-diketone derivative and synthesis method thereof
  • Spiro [cyclopropane-1, 2'-indene]-1', 3'-diketone derivative and synthesis method thereof

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Embodiment Construction

[0024] The following are specific embodiments of the present invention and in conjunction with the accompanying drawings, the technical solutions of the present invention are further described, but the present invention is not limited to these embodiments.

[0025] General method for the synthesis of substituted spiro[cyclopropane-1,2'-indene]-1',3'-dione derivatives

[0026] As shown in the reaction formula in the figure, the synthesis steps of spiro[cyclopropane-1,2'-indene]-1',3'-dione derivatives (I) provided by the present invention are as follows: add 0.1 mmol Sulfur ylide derivatives (Ⅱ) (such as: phenylthioylide, etc.), substituted 2-ethylene-1H-indene-1,3(2H)-dione compounds (Ⅲ) (such as: 2-ethylene Base-1H-indene-1,3(2H)-dione, etc.) 0.1mmol, base (such as: Cs 2 CO 3 etc.) 1.2mmol, then add 2~3ml solvent (such as: HFIP), react at room temperature, add water or saturated salt solution after the reaction, then extract with organic solvent, dry, distill and concentrate

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Abstract

The invention provides a spiro[cyclopropane-1, 2'-indene]-1', 3'-diketone derivative and a synthesis method thereof, and belongs to the technical field of organic synthesis of medical intermediates. The method comprises the following steps: adding a proper solvent and a proper alkali into a container filled with a substituted 2-ethylidene-1H-indene-1, 3 (2H)-diketone compound and a substituted sulfur ylide compound, stirring at a proper reaction temperature, filtering after the reaction is finished, adding water or a saturated salt aqueous solution into the filtrate, extracting with an organic solvent, carrying out drying, carrying out reduced pressure distillation concentration to remove the solvent, and carrying out column chromatography separation on the crude product to obtain the target product spiro[cyclopropane-1, 2'-indene]-1', 3'-diketone derivative.The method has the advantages of being efficient in reaction, convenient and rapid, wide in substrate adaptability, high in diastereoselectivity, high in yield and the like and has good industrial application prospects.

Description

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Claims

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Application Information

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Owner HUBEI UNIV OF SCI & TECH
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