Synthesizing method of alpha, beta unsaturated nitroolefin derivative

A technology of nitroalkenes and synthetic methods, which is applied in the formation/introduction of nitro/nitroso groups, preparation of nitro compounds, organic chemistry, etc., and can solve the problems of difficult industrial application, low yield and yield, environment and human body Harmful and other problems, to achieve the effect of industrial production, high stereoselectivity, easy separation and purification

Active Publication Date: 2017-08-11
YUANJIANG HUALONG CATALYST TECH
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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 difficu

Method used

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  • Synthesizing method of alpha, beta unsaturated nitroolefin derivative
  • Synthesizing method of alpha, beta unsaturated nitroolefin derivative
  • Synthesizing method of alpha, beta unsaturated nitroolefin derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1～21

[0057] Embodiment 1~21 all reacts by following reaction equation:

[0058]

[0059] The specific operation steps are: alkene (0.5mmol), NH 4 I (1.5 equivalents, 0.75mmol, 108mg), TBHP (70% H 2 O, 6.0 equiv, 3.0 mmol, 384 mg), TPPFeCl (3-5% on molar styrene) and acetonitrile (2 mL) were added to a sealed tube. Acetonitrile was added first, followed by olefin, NH 4 I and TPPFeCl, and finally TBHP. The reaction was stirred vigorously at 120 °C for 6 hours and monitored by TLC. After the reaction was complete, the mixture was cooled to room temperature, then filtered and washed with ethyl acetate (EA). Finally, the filtrate was concentrated with a rotary evaporator, and purified by column chromatography with silica gel (200-300 mesh) using petroleum ether (PE) / ethyl acetate (EA) as eluent.

Embodiment 1

[0061] Olefins: Target product: (C 8 h 7 NO 2 );

[0062] Yellow solid: 82% (61mg). 1 H NMR (400MHz, CDCl 3 )δ8.01(d, J=13.7Hz, 1H), 7.63–7.53(m, 3H), 7.47(tdd, J=8.5, 5.2, 3.6Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ139.04,137.06,132.11,130.01,129.35,129.10.GC-MS(m / z):149.+.

Embodiment 2

[0064] Olefins: Target product: (C 9 h 9 NO 2 ).

[0065] Yellow solid: 77% (63mg). 1 H NMR (400MHz, CDCl 3 )δ7.96(d, J=13.6Hz, 1H), 7.55(d, J=13.6Hz, 1H), 7.43(d, J=8.1Hz, 2H), 7.25(d, J=8.2Hz, 2H) ,2.40(s,3H). 13 C NMR (101MHz, CDCl 3 )δ143.04, 139.08, 136.17, 130.06, 129.12, 127.17, 21.56. GC-MS (m / z): 163.

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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...

Claims

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Application Information

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IPC IPC(8): C07B43/02C07C201/08C07C205/04C07C205/32C07C205/42C07C205/03C07C205/05C07D213/26C07D333/12
CPCC07B43/02C07C201/08C07D213/26C07D333/12C07C205/04C07C205/32C07C205/42C07C205/03C07C205/05
Inventor 郭灿城曹重仲郭欣
Owner YUANJIANG HUALONG CATALYST TECH
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