Synthesis, spectral characterization, single crystal and conformational study of 1,5-dimethyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-one derivatives

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• 作者：R. Venkateswaramoorthi^a ; J. John Francis Xavier^a ; K. Krishnasamy^a ; ^{krishbala56@yahoo.co.in} ; H. Saleem^b
• 关键词：2 ; 4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-one ; 1H&ndash ; 1H COSY ; HSQC ; NOESY ; Conformational study ; Crystal structure
• 刊名：Journal of Molecular Structure
• 出版年：2012
• 期刊代码：62_00222860
• 类别：ch
• 出版时间：28 March, 2012
• 卷：1012
• 期：Complete
• 页码：119-125
• 文件大小：685 K

摘要

1,5-Dimethyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-one 1 and their derivatives 2-8 were obtained by condensation of 2,6-dimethyl cyclohexanone, Ammonium acetate and substituted aromatic aldehydes and characterized by FT-IR, FT-Raman, ¹H NMR, ¹³C NMR, GC-MS, HOMOCOSY, HSQC, NOESY, single crystal X-ray diffraction analysis and theoretical DFT calculation. Compound 1 crystallized in the Triclinic system, space group P-1 with a = 6.8950(5) 呛, b = 11.5889(9) 呛, c = 11.9172(9) 呛, 伪 = 76.277(4)掳, 尾 = 78.000(3)掳, 纬 = 72.920(4)掳, V = 874.41(12) 呛³ and Z = 2. 1,5-Dimethyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-one 1 and their derivatives 2-8 were exist in boat-chair conformation with equatorial orientation of all the substituents at piperidine ring (two phenyl rings at C-2 and C-4 position, two methyl substituents at C-1 and C-5 position) of compound 1. In the crystal structure of compound 1, the molecules are connected by NH鈰疧C intermolecular hydrogen bonds. The existence of boat-chair conformation was confirmed by single crystal X-ray diffraction analysis and theoretical DFT calculation.