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A kind of synthetic method of n-hydrocarbyl-2,5-unsubstituted [60] fullerene pyrrolidine derivatives

A technology of fullerene pyrrolidine and a synthesis method, which is applied in the field of organic synthesis, can solve the problems of difficult to obtain catalyst, complex reaction system, poor product selectivity, etc., and achieves a wide range of substrate application, single reaction product, and easy separation and purification. Effect

Active Publication Date: 2022-02-22
WUHAN INST OF PHYSICS & MATHEMATICS CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The method reported above has its own limitations, and the method product selectivity that Suk Hyun Lim reports is poor, and product yield is low and reaction system is complicated, and the method catalyst of Airat R.Tuktarov report is difficult to obtain, and therefore urgently needs to develop the new synthetic material of this class. method

Method used

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  • A kind of synthetic method of n-hydrocarbyl-2,5-unsubstituted [60] fullerene pyrrolidine derivatives
  • A kind of synthetic method of n-hydrocarbyl-2,5-unsubstituted [60] fullerene pyrrolidine derivatives
  • A kind of synthetic method of n-hydrocarbyl-2,5-unsubstituted [60] fullerene pyrrolidine derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] [60] Preparation of fullerene pyrrolidine derivative A:

[0041]

[0042] Concrete preparation steps are:

[0043] [60] fullerene (36.0mg, 0.05mmol), paraformaldehyde (22.5mg, 0.75mmol), (185 μL, 1.25 mmol) was added to a 50 mL round bottom flask. Ultrasound was used to dissolve completely in 6mL of o-dichlorobenzene, and then the mixture was immediately heated and stirred in an oil bath whose temperature was preset at 180°C for 15 minutes, and the reaction process was traced by thin-layer chromatography (TLC) spot plate , stop the reaction at the end of the reaction. After the reaction is over, the reaction mixture is filtered through a short silica gel column to remove insoluble substances. The solvent is spin-out under reduced pressure in a rotary evaporator, and the residue is separated by column chromatography, using carbon disulfide as the eluent. The first thing to be separated is Unreacted [60]fullerene, followed by brown product [60]fullerene pyrrolidine...

Embodiment 2

[0046] [60] Preparation of fullerene pyrrolidine derivative B:

[0047]

[0048] Concrete preparation steps are:

[0049] [60] fullerene (36.0mg, 0.05mmol), paraformaldehyde (22.5mg, 0.75mmol), (158 μL, 1.25 mmol) was added to a 50 mL round-bottomed flask, sonicated with an ultrasonic instrument to completely dissolve in 6 mL of o-dichlorobenzene, and then the mixture was immediately heated and stirred in an oil bath with a preset temperature of 180 °C for 35 Minutes, the reaction process was followed by thin-layer chromatography (TLC) spot plate, and the reaction was stopped at the end of the reaction. After the reaction is over, the reaction mixture is filtered through a short silica gel column to remove insoluble substances. The solvent is spin-out under reduced pressure in a rotary evaporator, and the residue is separated by column chromatography, using carbon disulfide as the eluent. The first thing to be separated is Unreacted [60]fullerene followed by [60]fullerene ...

Embodiment 3

[0052] [60] Preparation of fullerene pyrrolidine derivative C:

[0053]

[0054] Concrete preparation steps are:

[0055] [60] fullerene (36.0mg, 0.05mmol), paraformaldehyde (22.5mg, 0.75mmol), (211 μL, 1.25 mmol) was added to a 50 mL round bottom flask. Ultrasonic sonication was used to completely dissolve in 6 mL of o-dichlorobenzene, and then the mixture was immediately heated and stirred in an oil bath whose temperature was preset at 180°C for 20 minutes, and the reaction process was tracked by thin-layer chromatography (TLC) spot plate , stop the reaction at the end of the reaction. After the reaction is over, the reaction mixture is filtered through a short silica gel column to remove insoluble substances. The solvent is spin-out under reduced pressure in a rotary evaporator, and the residue is separated by column chromatography, using carbon disulfide as the eluent. The first thing to be separated is Unreacted [60]fullerene, followed by brown product [60]fulleren...

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Abstract

The invention discloses a method for synthesizing N-hydrocarbyl-2,5-unsubstituted [60] fullerene pyrrolidine derivatives, belonging to the technical field of synthesis of fullerene derivatives. The specific process of the synthesis method of the present invention is: using [60] fullerene, paraformaldehyde, and primary amine as raw materials, react at a certain temperature in the next step to generate N-hydrocarbyl-2,5-unsubstituted [60] fullerene Pyrrolidine derivatives. The synthesis method of the invention has the advantages of cheap and easy-to-obtain raw materials, simple synthesis process, wide application range of substrates, single product, etc., and broad application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing N-hydrocarbyl-2,5-unsubstituted [60]fullerene pyrrolidine derivatives. Background technique [0002] Fullerene pyrrolidine is the most extensively studied class of fullerene derivatives, and it has applications in drug synthesis, light-controlled field-effect transistors, and organic solar cells. There are many synthetic methods for fullerene pyrrolidines, mainly including Prato reaction and newly developed reactions based on aldehydes and amines. However, these known methods still have great difficulties in preparing fullerene pyrrolidines with specific structures. For example, due to the limited types of N-substituted amino acids, it is not easy to obtain N-hydrocarbyl-2,5-unsubstituted [60]fullerene pyrrolidine by Prato reaction. So far, only a few research groups have reported the synthesis of N-hydrocarbyl-2,5-unsubstituted [60...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/70C07D409/06
CPCC07D209/70C07D409/06
Inventor 汪慧娟刘朝阳李法宝李云飞
Owner WUHAN INST OF PHYSICS & MATHEMATICS CHINESE ACADEMY OF SCI