一维NOESY和HOHAHA技术用于苯环壬酯的立体结构研究

Structural Determination of Phencyclonate by 1D-HOHAHA and 1D-NOESY NMR Spectroscopy

中枢抗胆碱药物苯环壬酯2′苯基2′环戊基2′羟基乙酸N甲基3氮杂双环(3,3,1)壬9α酯的化学结构比较复杂,部分谱峰重叠,本文采用2种NMR新方法,MMDY混合脉冲梯度选择一维HOHAHA和多重激发梯度选择一维NOESY相结合对其1HNMR和立体化学进行了研究,重叠谱峰的归属得到确定.根据NOE实验结果,证实该化合物为9α差向异构体,并且确定了在氘代氯仿中氮杂双环为椅式椅式构象;哌啶环中氮甲基位于e键.本结果有助于此类化合物的化学结构和溶液构象的测定.

Phencyclonate { 2＇-pheny-2＇-cycloamyl-2＇-hydroxyacetic-N-methly-3-azabiclo [3, 3, 1] nonane-9a-carboxylate} was synthesized and studied by 1D-HOHAHA and 1D-NOESY NMR spectroscopy employing frequency-selective radiofrequency pulses and pulsed field gradients. The results showed that all protons in the compound could be assigned by the combined use of the two techniques. Based on the results obtained from the 1D-NOESY experiment, the conformational property and C-9 configuration were elucidated as （1A）.