Fluoroalkyl substituted furyl monophosphine oxide compound and preparation method thereof

Abstract

The invention discloses a fluoroalkyl substituted furyl monophosphine oxide compound and a preparation method thereof. The preparation method comprises the following steps: adding an alkali promoter and a solvent into a reaction raw material formed by mixing a polyfluoroalkyl substituted peroxide compound and an organic phosphine oxide compound, stirring and reacting for 1-24 h in an air atmosphere at room temperature, determining a reaction process by TLC detection, and obtaining a reaction product after the reaction is finished, wherein the molar volume ratio of the polyfluoroalkyl substituted peroxide compound to the organic phosphine oxide compound to the alkali promoter to the solvent is 1 mmol: (1-3) mmol: (2-6) mmol: (1-3) mL, and the solvent comprises chloroform, tert-butyl alcohol, acetonitrile and dichloromethane; and washing, extracting and drying the reaction product, and carrying out column chromatography separation to obtain the fluoroalkyl substituted furyl monophosphineoxide compound. The method disclosed by the invention is simple in required initial raw materials, wide in source and easy to prepare, and the obtained monophosphine oxide compound has a wide application prospect in the fields of drug synthesis, material research and related extension.

Description

technical field [0001] The invention belongs to the fields of organic chemistry and medicinal chemistry, and in particular relates to a fluoroalkyl-substituted furyl monophosphine oxide compound and a preparation method thereof. Background technique [0002] Arylphosphorus oxides have attracted attention due to their numerous applications in organic synthesis, materials science, medicinal chemistry, and biochemistry. Organophosphine ligands can be obtained conveniently and efficiently by reducing aryl phosphine oxides, which is of great significance for the construction of ligand libraries for phosphine-containing compounds. Due to the wide use of this class of compounds, new requirements are continuously put forward for the development of their synthetic methods. [0003] The classic construction methods of aromatic C-P bonds include organometallic nucleophilic substitution reactions, nucleophilic substitution reactions of phosphating electrophiles (Tetrahedron Lett., 1995...

AI Technical Summary

Problems solved by technology

Although these reactions have achieved remarkable progress in terms of efficiency, functional group tolerance, and reaction selectivity, high temperatures (generally above 100 °C), expensive transition metals, and long reaction time, which still somewhat limits the practicality of the reaction

Especially the realization of phosphine oxidation based on heterocyclic compounds is still relatively difficult

[0005] In addition, the directional introduction of fluorine and polyfluoroalkyl functional groups in the target molecule can often significantly change its physical and chemical properties, but the existing reported methods are rarely able to simultaneously introduce fluoroalkyl substituents during the construction of the furanic compound skeleton , and simultaneously achieve phosphine oxidation for the construction of novel fluoroalkyl-substituted furyl bisphosphine oxides and fluoroalkyl-substituted furyl monophosphine oxides

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