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Alpha, beta-nonsaturated nitroolefin compound eco-friendly synthesis method

A nitroolefin and green synthesis technology, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of multi-step, good yield, and low yield, etc., to achieve atomic efficiency and reduce impact , the effect of cheap raw materials

Inactive Publication Date: 2015-06-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After acylation of β-nitroalcohol, treatment with sodium carbonate in refluxing benzene solution can obtain α,β-unsaturated nitroalkenes in good yield, but the reaction requires multiple steps and the yield is not very high

Method used

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  • Alpha, beta-nonsaturated nitroolefin compound eco-friendly synthesis method
  • Alpha, beta-nonsaturated nitroolefin compound eco-friendly synthesis method
  • Alpha, beta-nonsaturated nitroolefin compound eco-friendly synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of the first step ionic liquid

[0055] Take tetrabutylphosphorus hydroxide aqueous solution (mass concentration 40%) (6.9g, 25mmol) and equimolar amount of imidazole (0.7g, 25mmol), stir at room temperature for 48h, remove water and dry to obtain a colorless transparent liquid, vacuum at 80°C Dry for 12h to obtain ionic liquid [P(n-Bu) 4 ][Im], the structural formula is as follows:

[0056]

[0057] The second step Henry reaction

[0058] Functionalized ionic liquid [P(C 2 h 5 ) 4 ][Im] (1.0g, 3.1mmol) and 1mL of water were added to a 50mL microblogging quartz tube, stirred at room temperature until homogeneous, nitroethane (0.1g, 2.5mmol) and benzaldehyde (0.26g, 2.5mmol) were sequentially Add it into the reaction vessel, seal it with a microwave polytetrafluoroethylene cover, stir for 30 minutes under microwave conditions (temperature 60°C, power 400W), and cool to room temperature. Take a small amount of the reaction mixture to do 1 H NMR chara...

Embodiment 2-5

[0063] Microwave temperature is as described in Table 1, other reaction reaction conditions: functionalized ionic liquid [P(n-Bu) 4 ] [Im], water consumption, reaction time, reactant consumption and product yield calculation are reacted with the henry among the embodiment 1.

[0064] Table 1

[0065]

Embodiment 6-11

[0067] The reaction time is described in Table 2, other reaction reaction conditions: functionalized ionic liquid [P(n-Bu) 4 ] [Im], water consumption, reaction time, reactant consumption and product yield calculation are reacted with the henry among the embodiment 1. .

[0068] Table 2

[0069]

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PUM

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Abstract

The invention discloses an alpha, beta-nonsaturated nitroolefin compound eco-friendly synthesis method. The method comprises that saturated nitroparaffin and aromatic aldehyde as substrates undergo a full reaction in a functionalized ionic liquid-water catalysis system at a temperature of 20-150 DEG C under the microwave conditions, and the produced mixture is subjected to extraction separation, purification and drying so that an alpha, beta-nonsaturated nitroolefin compound is obtained. The alpha, beta-nonsaturated nitroolefin compound eco-friendly synthesis method has the advantages of high efficiency, simpleness, mild reaction conditions, high yield, catalytic reaction system environmental friendliness, good repeatability, ionic liquid preparation environmental friendliness and good atom economy.

Description

technical field [0001] The invention relates to a green synthesis method of α, β-unsaturated nitroolefin compounds Background technique [0002] Nitroalkenes are a class of biologically active compounds that play an important role in many fields. 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. α,β-Unsaturated nitroalkenes are also widely used as Michael acceptors in some reactions, such as hydrogen bond-mediated Michael-Michael series reactions with high stereoselectivity; asymmetry between aldehydes, ketones and nitroalkenes Michael reaction; Stereoselective Friedel-Crafts alkylation of indole, pyrrole and nitroalkene; asymmetric Michael addition between nitroalkene and nitroalkane; tandem catalyzed non-catalytic reaction involving nitroalkane Symmetric Friedel-Crafts / Henry reaction; Asymmetric bioreduction of nitroalkenes; Domino n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/04C07C205/09C07C205/32
Inventor 高艳安王畅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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