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Fullerene pyrrolidine derivative and preparation method thereof

A technology of fullerene pyrrolidine and derivatives, which is applied in the preparation of organic compounds, preparation of amino hydroxyl compounds, chemical instruments and methods, etc., and can solve problems such as limited application, poor solubility, and unsatisfactory targeting

Active Publication Date: 2016-06-15
HUANGSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, C60 has poor solubility in polar solvents and unsatisfactory targeting, which limits its application in the biomedical field.

Method used

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  • Fullerene pyrrolidine derivative and preparation method thereof
  • Fullerene pyrrolidine derivative and preparation method thereof
  • Fullerene pyrrolidine derivative and preparation method thereof

Examples

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Embodiment 1

[0032] The method for preparing 3-(4-nitrophenyl)acrolein described in this embodiment comprises the following steps:

[0033] Get 5.0g (66mmol) of p-nitrobenzaldehyde and 10.0mL of acetaldehyde into the three-necked flask, add 10mL of 20% potassium hydroxide-methanol solution in the dropping funnel, stir magnetically, and cool the reaction with an ice-salt bath bottle, when the temperature drops to 0-5°C, slowly add 5mL potassium hydroxide-methanol solution dropwise under magnetic stirring, react for 40min, then add 5mL potassium hydroxide-methanol solution dropwise, continue to react at about 10°C for 40min, cool The reaction mixture solidifies below 5°C, add 16 mL of acetic anhydride, heat on a water bath for 30 min, pour into 120 mL of hot water, add 16 mL of concentrated hydrochloric acid, heat in a water bath for 20 min, and let stand for 24 h. Crystals were precipitated, filtered by suction, washed, and recrystallized in 30% aqueous acetic acid solution by mass fraction...

Embodiment 2

[0040] The method for preparing 3-(4-nitrophenyl)acrolein described in this embodiment comprises the following steps:

[0041] Get 5.0g (66mmol) p-nitrobenzaldehyde and 10.0mL acetaldehyde into the three-necked flask, add 10mL mass fraction of 10% potassium hydroxide-methanol solution in the dropping funnel, stir magnetically, and cool the reaction with an ice-salt bath bottle, when the temperature drops to 0-5°C, slowly add 5mL potassium hydroxide-methanol solution dropwise under magnetic stirring, react for 40min, then add 5mL potassium hydroxide-methanol solution dropwise, continue to react at about 10°C for 40min, cool The reaction mixture solidifies below 5°C, add 16 mL of acetic anhydride, heat on a water bath for 30 min, pour into 120 mL of hot water, add 16 mL of concentrated hydrochloric acid, heat in a water bath for 20 min, and let stand for 24 h. Crystals were precipitated, suction filtered, washed, and recrystallized in 30% aqueous acetic acid solution to obtain 1...

Embodiment 3

[0043] The method for preparing 3-(4-nitrophenyl)acrolein described in this embodiment comprises the following steps:

[0044] Get 5.0g (66mmol) of p-nitrobenzaldehyde and 10.0mL of acetaldehyde into the three-necked flask, add 10mL of 30% potassium hydroxide-methanol solution in the dropping funnel, stir magnetically, and cool the reaction with an ice-salt bath bottle, when the temperature drops to 0-5°C, slowly add 5mL potassium hydroxide-methanol solution dropwise under magnetic stirring, react for 40min, then add 5mL potassium hydroxide-methanol solution dropwise, continue to react at about 10°C for 40min, cool The reaction mixture solidifies below 5°C, add 16 mL of acetic anhydride, heat on a water bath for 30 min, pour into 120 mL of hot water, add 16 mL of concentrated hydrochloric acid, heat in a water bath for 20 min, and let stand for 24 h. Crystals were precipitated, filtered with suction, washed, and recrystallized in 30% aqueous acetic acid solution to obtain 1.6 ...

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PUM

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Abstract

The invention belongs to the technical field of chemical synthesis, particularly relates to a N-methyl-2-(4-nitrobenzene vinyl)-3,4-fullerene pyrrolidine derivative, and further discloses a preparation method of the fullerene pyrrolidine derivative. The method for preparing N-methyl-2-(4-nitrobenzene vinyl)-3,4-fullerene pyrrolidine comprises the steps that the existing 1,3-dipolar-cycloaddition reaction is utilized, methylbenzene is used as a solvent for a reaction, and the target product N-methyl-2-(4-nitrobenzene vinyl)-3,4-fullerene pyrrolidine is obtained. It is surprised to find that after the whole reaction system is cooled to indoor temperature, an organic solvent comprising trichloromethane, carbon disulfide and orthodichlorobenzene is added, the reaction continues to be carried out to the end, the synthetic yield of the product is far higher than that of the product obtained through the solvent only comprising methylbenzene, and the unexpected technical effect is obtained.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, specifically relates to an N-methyl-2-(4-nitrostyryl)-3,4-fullerene pyrrolidine derivative, and further discloses a preparation method thereof. Background technique [0002] In 1985, when scientists such as R.F.Crul, R.E.Smallay and H.W.Kroto of the United Kingdom used high-energy laser pulses to graphite, they accidentally discovered a series of carbon ion clusters represented by C60, which were later called fullerenes or football enes. Fullerene thus stands out as the third allotrope of carbon. Later, inspired by the vaulted dome designed by architectural designer Buckminster Fuller, Kroto and others finally determined that C60 has a closed spherical cage structure similar to the vaulted dome, which is consistent with the "stable" nature of C60 match. [0003] [0004] Fullerene is the third allotrope of carbon. Its unique three-dimensional spherical space structure and numerous...

Claims

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Application Information

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IPC IPC(8): C07D209/96C09K11/06B01J31/02C07C213/00C07C215/76
CPCB01J31/0244C07C213/00C07D209/96C09K11/06C09K2211/1007C09K2211/1029C07C215/76
Inventor 黄飞魏先文
Owner HUANGSHAN UNIV
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