20101213_第五讲-氮杂环化合物的核磁共振谱.ppt

氮杂环化合物的核磁共振谱 胺类化合物的手性 胺类化合物的手性 胺类化合物的手性 Azacyclohexanes Isoxazolidines Isoxazolidines Isoxazolidines Isoxazolidines Isoxazolidines Isoxazolidines Isoxazolidines Isoxazolidines Isoxazolidines Azacyclohexanes Steroidal Neuromuscular Blocking Drugs Steroidal Neuromuscular Blocking Drugs Steroidal Neuromuscular Blocking Drugs 哌嗪类化合物 哌嗪类化合物 哌嗪类化合物 Piperazine dihydrochloride salt Piperazine dihydrochloride salt Piperazine dihydrochloride salt 盐酸西替利嗪 盐酸西替利嗪 盐酸洛美利嗪 哌嗪衍生物 哌嗪衍生物 哌嗪衍生物 哌嗪衍生物 哌嗪衍生物 哌嗪衍生物 Buspirone analogues Buspirone analogues Buspirone analogues 李　茜, 沈文斌, 邹巧根，药学学报 2003 ,38(10) :767 - 770 张尊建, 李　茜, 沈文斌, 徐云根，中国药科大学学报 2003 ,38(10) :767 - 770 307K 297K 297K+1 drop H2O 322K 317K 297K+2 drop H2O 297K+4 drop H2O 297K 297K+1 drop H2O 322K 297K+4 drop H2O L.H. Gan et al. J. Colloid Interface Sci. 183, 329–338 (1996) L.H. Gan et al. J. Colloid Interface Sci. 183, 329–338 (1996) L.H. Gan et al. J. Colloid Interface Sci. 183, 329–338 (1996) 两边的取代基相同 L.H. Gan et al. J. Colloid Interface Sci. 183, 329–338 (1996) 两边的取代基相同 L.H. Gan et al. J. Colloid Interface Sci. 183, 329–338 (1996) L.H. Gan et al. J. Colloid Interface Sci. 183, 329–338 (1996) Z. Chilmonczyk et al. J. Mol. Struct. 385, 195–207 (1996) kaspar Z. Chilmonczyk et al. J. Mol. Struct. 385, 195–207 (1996) Freebase in CD2Cl2+CFCl3 Hydrochloride in CDCl3 15 18 21,21’ 15 kaspar Z. Chilmonczyk et al. J. Mol. Struct. 385, 195–207 (1996) 15 kaspar * * Structure of Amines ammonia 氨 ammonium salts 铵盐 amine 胺 primary amine secondary amine tertiary amine quaternary ammonium salts季铵盐 极快速的翻转使得我们不能区分对映体的存在。 enantiomers that can be resolved 对映体可以能拆分开 胺类化合物的手性 在环状化合物中，氮原子的翻转速度大大降低，在室温下就可以区分对映体。 There is a conformational change in the ring as well as inversion at the pyramidal nitrogen. Therefore it is difficult to say whether the axial-equatorial equilibrium is achieved by ring inversion, or by nitrogen inversion SA Ali et al. Can. J. Anal. Sci. Spectrosc. 53, 66-74,2008 Synthesis of isoxazolidines SA Ali et al. Can. J. Anal. Sc