Preparation method of olefin phosphate compound

Abstract

The invention discloses a preparation method of an olefin phosphate compound. The method comprises the following steps: arylethylene and phosphate according to a mol ratio 1:4-6 are used as raw materials; ferric chloride and copper salt are used as catalysts, and di-tert-butyl peroxide is used as an oxidizing agent; the raw materials and triethylamine are mixed, an organic solvent is added, and under the protection of inert gas, a reaction is carried out at 90-110 DEG C; after the reaction ends, washing is carried out, rotary evaporation is used for removing the solvent, and column chromatography is carried out in order to obtain the olefin phosphate compound. Base metal copper and iron are used as catalysts, reactant arylethylene and phosphate have low price, toxicity is low, the oxidizing agent is green and environmentally friendly, and the yield of the synthetic reaction of the olefin phosphate compound is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of enophosphate compounds. Background technique [0002] Elenyl phosphate compounds are a class of organic synthesis intermediates that are widely used, and can be used to synthesize bioactive molecules, flame retardants, and polymer additives. Enenophosphate compounds are also widely used in Michael addition and Horner-Wadsworth-Emmons (HWE) reactions to realize the synthesis of compounds. At the same time, the enphosphonate compound can also be used as the precursor of L-AP4, an effective drug for treating central nervous diseases such as Parkinson's disease and Alzheimer's disease. Therefore, it is of great importance to develop efficient organic synthesis methods for the synthesis of enophosphate compounds. [0003] At present, the main synthesis methods of enophosphonates are the addition phosphorylation of alkynes and the phosphorylation o...

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Problems solved by technology

Transition metals Pd, Pt, Rh, etc. can effectively realize the hydrogen phosphorylation of terminal alkynes, thereby realizing the synthesis of enophosphoesters. However, this method often has some disadvantages, such as the stereoselectivity of the reaction process is not easy to control, A mixture of Z / E configuration products will be generated, or the reaction requires noble metals for catalysis ([1] Liu, L.; et al. Experimental and Theoretical Studies on Nickel–Zinc-Catalyzed Cross-Coupling of Gem-Dibromoalkenes with P (O)–H Compounds[J].RSC Advances.2014,4:2322-2326.[2]Han,L.; et al.Palladium-Catalyzed Dehydrogenative Cis Double Phosphorylation of Alkynes with H-Phosphonate Leading to(Z)- Bisphosphoryl-1-alkenes. J.Am.Chem.Soc[J].2008:130,2752-2753.)

Phosphorylation of substituted alkenes is also an effective method for the synthesis of enophosphonate compounds, but the reaction produces equivalent by-products, so the atom economy is not high

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