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A kind of synthetic method of nitroalkene compound

A synthesis method and nitroolefin technology, applied in the field of synthesis of nitroolefin compounds, can solve the problems of difficult post-processing, low reaction yield, expensive raw materials, etc., and achieve strong substrate universality, few side reactions, The effect of easy operation

Active Publication Date: 2020-05-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the former method reacts under alkaline conditions, with many side reactions and difficult post-processing; the latter method has expensive raw materials and low reaction yield

Method used

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  • A kind of synthetic method of nitroalkene compound
  • A kind of synthetic method of nitroalkene compound
  • A kind of synthetic method of nitroalkene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add 0.3mmol of o-phenylcinnamaldehyde and 0.45mmol of copper nitrate trihydrate into a 15mL pressure-resistant tube, and then add 3mL of a mixture of acetonitrile and water (V (acetonitrile): V (water) = 100:1) as a solvent. Then, magnetic stirring was performed at 130° C. for 12 h. Then, two spoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the residue was separated by column chromatography, and V (petroleum ether): V (ethyl acetate ) = 20:1 mixed solution was used as eluent to elute, the eluate containing the target product was collected, and the solvent was evaporated to obtain a pure product, the amount of which was 0.174 mmol. The material was a yellow solid with the chemical name 2-nitro-ortho-styrene, and the yield was 58%.

[0033] Characterization data: 1 H NMR (CDCl 3 ,500MHz):8.08(d,J=13.5Hz,1H),7.68(d,J=8.0Hz,1H),7.58-7.44(m,7H)...

Embodiment 2

[0035]

[0036] Add 0.3mmol of o-phenylcinnamaldehyde and 0.3mmol of silver nitrate into a 15mL pressure-resistant tube, and then add 3mL of acetonitrile and water mixture (V (acetonitrile): V (water) = 50:1) as a solvent. Then, magnetic stirring was performed at 150° C. for 24 h. Then, two spoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the residue was separated by column chromatography, and V (petroleum ether): V (ethyl acetate ) = 20:1 mixed solution was used as eluent to elute, the eluate containing the target product was collected, and the solvent was evaporated to obtain the pure product, the amount of the pure product was 0.162 mmol. The material was a yellow solid with the chemical name 2-nitro-o-styrene, yield 54%.

[0037] Characterization data: 1 H NMR (CDCl 3 ,500MHz):8.08(d,J=13.5Hz,1H),7.68(d,J=8.0Hz,1H),7.58-7.44(m,7H),7.34-7.32(m,2H); 13...

Embodiment 3

[0039]

[0040] Add 0.3 mmol of o-phenylcinnamaldehyde and 0.9 mmol of ferric nitrate nonahydrate into a 15 mL pressure-resistant tube, and then add 3 mL of acetonitrile and water mixture (V (acetonitrile): V (water) = 500: 1) as a solvent. Then, magnetically stirred at 100° C. for 8 h. Then, two tablespoons of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and the residue was separated by column chromatography, and V (petroleum ether): V (ethyl acetate )=20:1 mixed solution was used as the eluent to elute, the eluate containing the target product was collected, and the solvent was evaporated to obtain the pure product, the amount of the pure product was 0.111 mmol. The material was a yellow solid with the chemical name 2-nitro-o-styrene, yield 37%.

[0041] Characterization data: 1 H NMR (CDCl 3 ,500MHz):8.08(d,J=13.5Hz,1H),7.68(d,J=8.0Hz,1H),7.58-7.44(m,7H),7.34-7....

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Abstract

The invention relates to a method for synthesizing an organic compound. The method is used for solving the problem of current synthesis of nitroolefin compounds that reaction byproducts are numerous,raw materials are expensive, and some methods are relatively troublesome in aftertreatment. The invention provides a method for preparing a nitroolefin compound. The nitroolefin compound is prepared through subjecting a cinnamyl aldehyde compound, which serves as a starting material, to a reaction with a nitrate and a solvent for 1 to 24 hours at the temperature of 25 DEG C to 150 DEG C. A methodfor direct nitration by using a cheap nitrate is achieved. The method is a new route for synthesizing the nitroolefin compound.

Description

[0001] (1) Technical field [0002] The invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing nitroolefin compounds. [0003] (2) Background technology [0004] Nitroolefin compounds are important intermediates in organic synthesis. The existence of nitro groups in these compounds makes the conjugated olefins polarized, easy to add to nucleophiles, and various substitutions can be added to unsaturated carbons. bases for the synthesis of various biologically active compounds. Therefore, nitroalkenes are very important synthons in the synthesis of natural products and pharmaceuticals. [0005] There are two traditional synthetic methods of nitroalkene compounds: (1) under alkaline conditions, carry out the Henry reaction and then condense aromatic aldehydes and nitroalkanes (Chemical Bulletin, 1993, 4, 6-12); ( 2) Prepared from alkenes, using organic selenium to convert inactive alkenes into nitroalkenes (Org. Preg. Proced....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/10C07C205/04C07C205/09C07C205/32
Inventor 刘运奎张海峰鲍汉扬
Owner ZHEJIANG UNIV OF TECH
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