手性双哌啶氨基醇衍生物的合成  

Synthesis of Chiral Amino Alcohol Derivatives with Bispidine Moiety

作　　者：王芳[1] 张月成[1] 冉维津[1] 赵继全[1] 

机构地区：[1]河北工业大学化工学院,天津300130

出　　处：《化学世界》2010年第9期541-544,564,共5页Chemical World

基　　金：国家自然基金青年科学基金项目(20806020)

摘　　要：由简单的烷基胺与丙烯酸甲酯为原料,经Michael加成、Dieckmann环合、脱羧得到三种N-烷基-4-哌啶酮。这些N-烷基-4-哌啶酮分别与(R)-(-)-2-氨基-1-丁醇和多聚甲醛进行Mannich反应,再经黄鸣龙还原得到三种新的具有手性的双哌啶氨基醇衍生物。采用1H NMR、13C NMR、IR、MS对目标产物的结构进行了表征,并对其旋光度进行了测定。Mannich反应优化条件为:甲醇回流温度下反应,物料摩尔比为n(N-烷基-4-哌啶酮)∶n((R)-2-氨基-1-丁醇)∶n(多聚甲醛)=1∶1.2∶2.5。Three N-alkyl-4-piperidones were synthesised through the Michael addition of alkyl amines and methyl acrylate and followed by Dieckmann cyclization and decarboxylation.The N-alkyl-4-piperidones reacted with（R）-（-）-2-amino-1-butanol and paraformaldehyde through Mannich reaction followed by HUANG Mi-lon reduction to afford three new chiral amino alcohol derivatives with bispidine moiety.The structures of the final products were characterized by ^1H NMR, ^13C NMR,IR and MS.Their optical rotation was also determined.The optimum reaction conditions of the Mannich reaction were as follows： reacting at reflux temperature of methanol and the mole ratio of n（N-alkyl-4-piperidone）∶n（（R）-（-）-2-amino-1-butanol）∶n（paraformaldehyde）=1∶1.2∶2.5.

关 键 词：(R)-(-)-2-氨基-1-丁醇 N-烷基-4-哌啶酮 双哌啶 手性氨基醇衍生物 

分 类 号：O626.3[理学—有机化学]