吲哚喹嗪类化合物的~1H NMR及立体化学研究  

STUDY ON ~1H NMR AND STEREOCHEMISTRY OF INDOLOQUINOLIZINE DERIVATIVES

作　　者：江忝益 彭师奇[1] 杨宪斌[1] 张志亮[1] Ekkehard Winterfeldt 

机构地区：[1]北京医科大学天然药物及仿生药物国家重点实验室,100083 [2]Institute,fur,Organische,Chemie,Universitat,Hannover,西德

出　　处：《波谱学杂志》1991年第4期403-414,共12页Chinese Journal of Magnetic Resonance

摘　　要：以对应的光学活性四氢β-咔啉在相转移条件下经Aldol缩合、脱水生成的光学活性吲哚喹嗪,与例如丙二酸二甲酯发生Michael加成时,显示高度的立体专属性。作为有广泛用途的建筑块,本文提供了六个代表性化合物的2D-NMR的同核二维相关谱(COSY)和同核欧沃豪斯谱(NOESY)。根据实验测得的NOE关系,满意地指定了化合物中新引人的手性碳的构型,借助分子模型,讨论了它们的构象及Michael反应的反应活性差异。Under phase transfer condition enantiomerically pure tetrahydro - ???? - carboline underwent Aldol condensation and dehydration gave rise to corresponding indoloquinolizine. The Michael addition of indoloquinolizine and methyl malonate showed high stereospecificity which depends on the stereochemistry of the title compounds. In this paper COSY and NOESY of 2D-NMR spectroscopy for 6 indoloquinolizine derivatives were studied. In la and 2a there are NOE relationship between 12b - H and COCH, for Ib and 2bhowever there is not any NOE effect at all. In 3a there is NOE relationship between 12b-H and COCH_3 ; in 3b there is NOE relationship between 6-CO_2CH_3 and COCH_2 . Based on these results and Dreiding Stereomodels their configurations, conformations and reactivities of Michael additions with methyl malonate are discussed.

关 键 词：吲哚喹嗪 2D-NMR 立体化学 

分 类 号：O626.13[理学—有机化学]