C <sub> 60 </ Sub> Synthesis Of 1,3 - Dipolar Cycloaddition Reaction And Its Derivatives

As the third allotrope of carbon, fullerene displays widespread application prospects in chemistry, biology, material and medicine for its unique structure. In which the most representative [60]fullerence(C₆₀) has particular efficacy in anti-virus, inhibits proliferation of cancer cells, eliminates free radicals, dual function to the biofilm, causes DNA cleavage and so on. While dehydroabietic acid and its derivatives, which have a steroid-like multicyclic diterpene structure, have been recognized that they have biological activies as sterilization etc.. It is significant to intergrate C₆₀ with dehydroabietylamine, which is one of the dehydroabietic acid derivatives, into one new molecule, and to study the bioactivity of this new molecule.In this paper, as one of the reactants, dehydroabietylamine was purified at first, and then chloroactic acid was added with ethanol/water as solvent. The nucleophilic substitution was catalysised by KOH at 60℃, and a novel compound N-carboxymethyl dehydroabietylamine was synthesized. The target compound, which was characterized by IR, 1H NMR and EI-MS, was preliminary tested in bioactivity. The result showed that high concentration(50mg/mL) ethanol solution of the target compound had certain inhibiting effects on Phanerochaete chrysosporium, Coriolus versicolor and the effects would be weakened if reduces the density(5mg/mL). But it had no inhibiting effects on Gloeophyllum trabeum and Poria vaporaria no matter high concentration ethanol solution or low.The 1,3-dipolar cycloaddition reaction of C₆₀ was also researched in this paper. A novel fulleropyrrolidine derivative that has never been reported before, was synthesized by reaction of N-carboxymethyl dehydroabietylamine, formaldehyde and C₆₀, through the 1,3-dipolar cycloaddition reaction reacted at reflux temperature with toluene as solvent. The result compound was characterized by IR, 1H NMR , 13C NMR and MALDI-TOF-MS.Based on fulleropyrrolidine derivative which was synthesized in front, another novel water soluble fulleropyrrolidine derivative was synthesized by reaction of fulleropyrrolidine derivative and NaOH, in toluene/water mixed solution at reflux temperature, with TBAH and H₂O₂ as the catalysts. The result compound was characterized by IR, 1H NMR and MALDI-TOF-MS, and the number of hydroxyl groups, which was added to the cage of fullerene, was infered to 6.