Synthesizing method of alpha, beta unsaturated nitroolefin derivative

Abstract

The invention discloses a synthesizing method of an alpha, beta unsaturated nitroolefin derivative. The synthesizing method includes: allowing an alkene compound to have one-pot reaction in a tert-butyl hydroperoxide system containing tetra-arylated ferroporphyrin (III) and halogenated ammonium salt to generate the alpha, beta unsaturated nitroolefin derivative. By the method, the alpha, beta unsaturated nitroolefin derivative with high E three-dimensional selectivity is synthesized under mild reaction conditions in a high-yield manner.

Description

technical field [0001] The present invention relates to a kind of synthetic method of α, β-unsaturated nitro olefin derivatives, particularly a kind of alkene compound containing tetraaryl porphyrin iron (III), ammonium halide salt and tert-butyl hydroperoxide The invention discloses a method for synthesizing trans-α,β-unsaturated nitroolefin derivatives with high yield and high selectivity in one-pot reaction in a system, belonging to the field of organic synthesis. Background technique [0002] α,β-Unsaturated nitroalkenes are a class of biologically active compounds. For example, unsaturated nitro fatty acids are a new class of endogenous anti-inflammatory mediators; unsaturated nitrooleic acid can prevent renal ischemia and reperfusion injury in rats. At the same time, α,β-unsaturated nitroalkenes are an important class of drugs and organic intermediate compounds, which can be easily converted into a variety of different compounds and play an important role in many fiel...

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Problems solved by technology

Such as Chinese patent (CN106083597A) discloses a kind of synthetic method of conjugated nitroalkene, under the condition that diamine exists, utilize fatty aldehyde and the nitro group of nitroalkane to carry out aldol condensation reaction, by adding acid in the reaction process The elimination reaction of the conjugated nitroalkene carried out (as reaction 2); This method uses diamine as the catalyzer of nitro aldol condensation reaction, reduces side reaction generation, improves product yield, but this reaction step is many, has a large amount of acidity Waste liquid generation, polluting the environment

Chinese patent (CN 104710315 A) discloses a green synthesis method of α,β-unsaturated nitroolefin compounds (such as reaction 3), which uses functionalized ionic liquid and water as the catalytic system, aromatic aldehyde and nitroalkane Microwave heating reaction can make the reaction conditions mild and increase the reaction yield; however, the cost of ionic liquid used in this method is high and it is difficult to be applied industrially

The patent (CN1438977A) of Sabao Group Company of Italy's application in China discloses that styrene derivatives are used as raw materials, and the mixture of inorganic nitrite and iodine in the presence of peroxides is a nitrating reagent to synthesize nitrostyrene compounds; the method Due to the use of oxidants, the amount of iodine used in the process of nitrating olefins is greatly reduced, thereby improving the yield of the product to a certain extent and simplifying the process steps. However, these methods all use nitrite as the nitrating reagent, which is harmful to the environment and human body.

At present, there are still some nitrogen-containing oxides used as nitrating reagents to directly carry out nitration reaction with alkene compounds under the catalysis of metal nickel oxides to obtain nitroalkene derivatives (such as reaction 4). This method adopts gas-liquid reaction mode, the reaction efficiency is low, and toxic gas will be produced, and the yield yield is not high

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