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Synthetic method of [60] fullerocyclopentanone and [60] fullero 2-cyclohexenone compounds

A technology for cyclohexenones and synthesis methods, which is applied in the preparation of organic compounds, preparation of carbon-based compounds, chemical instruments and methods, etc., can solve the problems of environmental pollution and substrate limitations, and achieve high yield and application Wide and functional group compatibility

Active Publication Date: 2018-11-23
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, transition metal-involved methods are substrate-limited and environmentally polluting

Method used

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  • Synthetic method of [60] fullerocyclopentanone and [60] fullero 2-cyclohexenone compounds
  • Synthetic method of [60] fullerocyclopentanone and [60] fullero 2-cyclohexenone compounds
  • Synthetic method of [60] fullerocyclopentanone and [60] fullero 2-cyclohexenone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation of [60]fullerenocyclopentanones 2a:

[0015]

[0016] Reaction steps:

[0017] 0.05mmol C 60 , 0.015mmol catalyst 0.015mmol sodium ethoxide, 0.05mmol p-benzoquinone and 0.15mmol substrate 1a Add to a 25mL dry Shrek tube, then add dry 4mL anhydrous o-dichlorobenzene and 1mL anhydrous dichloromethane, seal the Shrek tube, ultrasonically dissolve the reactant completely, and then place it in a nitrogen atmosphere React in an oil bath at 90°C, stop the reaction after TLC detects that the reaction is complete, cool to room temperature, filter out the insoluble matter first, then spin off the organic solvent under reduced pressure, pack the column with thin-layer chromatography silica gel, load the sample by wet method, and use Carbon disulfide was eluted as an eluent to obtain the target product [60]fullerenocyclopentanone compound 2a, and the relative yield of product 2a was 56%.

[0018] 2a: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ7.69(d, J=7.6Hz, 2H), 7.42...

Embodiment 2

[0023] Preparation of [60]fullerenocyclopentanone 2b:

[0024]

[0025] Reaction steps:

[0026] 0.05mmol C 60 , 0.015mmol catalyst 0.015mmol sodium ethoxide, 0.05mmol p-benzoquinone and 0.15mmol substrate 1b Add to a 25mL dry Shrek tube, then add dry 4mL anhydrous o-dichlorobenzene and 1mL anhydrous dichloromethane, seal the Shrek tube, ultrasonically dissolve the reactant completely, and then place it in a nitrogen atmosphere React in an oil bath at 90°C, stop the reaction after TLC detects that the reaction is complete, cool to room temperature, filter out the insoluble matter first, then spin off the organic solvent under reduced pressure, pack the column with thin-layer chromatography silica gel, load the sample by wet method, and use Carbon disulfide was eluted as an eluent to obtain the target product [60]fullerenocyclopentanone compound 2b, and the relative yield of product 2b was 67%.

[0027] 2b: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ7.60(d, J=8.4Hz, 2H), 6.93(...

Embodiment 3

[0032] Preparation of [60]fullerenocyclopentanone 2c:

[0033]

[0034] Reaction steps:

[0035] 0.05mmol C 60 , 0.015mmol catalyst 0.015mmol sodium ethoxide, 0.05mmol p-benzoquinone and 0.15mmol substrate 1c Add to a 25mL dry Shrek tube, then add dry 4mL anhydrous o-dichlorobenzene and 1mL anhydrous dichloromethane, seal the Shrek tube, ultrasonically dissolve the reactant completely, and then place it in a nitrogen atmosphere React in an oil bath at 110°C, stop the reaction after TLC detects that the reaction is complete, cool to room temperature, filter out the insoluble matter first, then spin off the organic solvent under reduced pressure, pack the column with thin-layer chromatography silica gel, load the sample by wet method, and use Carbon disulfide was eluted as an eluent to obtain the target product [60]fullerenocyclopentanone compound 2c, and the relative yield of product 2c was 45%.

[0036] 2c: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ7.69(dd, J=8.8,5.2Hz,2H),7...

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Abstract

The invention discloses a synthetic method of [60] fullerocyclopentanone and [60] fullero 2-cyclohexenone compounds and belongs to the technical field of fullerene derivatives. The key points of the technical scheme of the invention are as follows: the synthetic method comprises the following step of by taking C60 and alpha, beta-unsaturated aldehyde compounds as reaction raw materials and organicmicromolecular N-heterocyclic carbine as a catalyst, realizing direct acylation of [60] fullerene through polarity inversion strategy of aldehyde to prepare the [60] fullerocyclopentanone and [60] fullero 2-cyclohexenone compounds as target products. In the synthetic method provided by the invention, the N-heterocyclic carbine as the organic micromolecular catalyst is used, and no metals participate to the reaction process, so that the synthetic process is environmentally friendly; a substrate is wide in application range and good in functional group compatibility; and the synthetic method has relatively high yield and is suitable for large-scale preparation.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fullerene derivatives, in particular to a method for synthesizing [60] fullerene cyclopentanone and [60] fullerene 2-cyclohexenone compounds. Background technique [0002] The wide application of fullerene derivatives in the fields of optoelectronic materials and biomedicine has made the chemical modification of fullerenes aroused extensive attention of chemists. By chemical method in C 60 The introduction of different groups on the surface to improve its physical and chemical properties such as solubility, energy level and electron affinity, and the modification of fullerenes is a current research hotspot. The traditional method of modifying fullerene is mainly cycloaddition reaction. In recent years, the method involving transition metals has shown high efficiency and attracted widespread attention. However, transition metal-involved methods are substrate-limited and pollute the environme...

Claims

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Application Information

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IPC IPC(8): C07C45/45C07C49/697C07C49/755C07C49/683
CPCC07C45/455C07C49/683C07C49/697C07C49/755C07C2603/97
Inventor 刘统信张朋玲张贵生胡贝贝
Owner HENAN NORMAL UNIV
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