Studies On The Synthesis,Characterization And Antibacterial Activity Of Derivatives From ω-formylcamphene

Turpentine is a renewable natural resource,its products are widely used in many field,including: chemical,pesticide,medical and fine chemical.Pinene,the main composition of turpentine,can be isomerized to camphene.Camphene can be used as medicine,perfume,antibacterial and material and so on.However,the deep processing and utilization of camphene remains at lower level and more efforts are required.In this dissertation,ω-formylcamphene was synthesized from camphene by the Vilsmeier-Haack reaction,then 28 new derivatives of ω-formylcamphene were designed and synthesized.Their structures were characterized by fourier transform infrared spectroscopy(FT-IR),nuclear magnetic resonance spectroscopy(1H NMR,13 C NMR)and electrospray ionization mass spectrometry(ESI-MS).Antibacterial activities of these derivatives were measured by oxford cup diffusion method.The main contents are as follows:(1)Ten novel ω-formylcamphene Schiff base compounds(3a~3j)were synthesized by the condensation of ω-formylcamphene and different substituted aromatic amines.(2)Isocamphylformaldehyde was prepared from the hydrogenation of ω-formylcamphene under Pd-C catalyst.Isocamphanylformic acid was synthesized by the oxidation of isocamphylformaldehyde.Seven novel endo-isocamphanylcarboxylic acid esters(6a~6g)were synthesized by the esterification of aliphatic monohydric alcohols and isocamphanylformic acid.At the same time,the effects of types and dosages of catalyst,different alcohols and reaction time on the esterification reactions were also investigated.(3)Isocamphanylformylchloride was synthesized from isocamphanylformic acid,and eleven endo-N-arylisocamphanylformamide(8a~8k)derivatives were prepared.Ten of them are new compounds.(4)Results of the preliminary antibacterial study show that Schiff base derivatives exhibit better antibacterial activity than ester derivatives and amides derivatives at the concentration of 10g/L,and esters derivatives demonstrate the weakest antibacterial activity against these four tested bacteria.Under P=0.05,compound 3i shows the best antibacterial activity against Escherichia coli,Pseudomonas aeruginosa and Staphylococcus aureus,the diameter of inhibition zone are 16.0 mm,19.0 mm and 16.1 mm,respectively.They are larger than the diameter of inhibition zone of positive control bromogeramine,which are 14.8 mm,18.0 mm and 15.8 mm respectively.Compound 2 exerts good antibacterial activity against Staphylococcus epidermidis and Escherichia coli,which are comparable to bromogeramine,and the diameter of inhibition zone of compound 2 are 17.3 mm and 14.8 mm respectively.Compound 3c exhibit comparable antibacterial activity to bromogeramine against Escherichia coli,its diameter of inhibition zone is 14.8mm.Compound 8d shows good antibacterial activity against Staphylococcus aureus,its diameter of inhibition zone is 16 mm,which is greater than bromogeramine.