Kania Iwona, Stadnicka Katarzyna, Oleksyn Barbara J
Faculty of Chemistry, Jagiellonian University, ul. Ingardena 3, 30-060 Kraków, Poland.
Chirality. 2004 Mar;16(3):180-9. doi: 10.1002/chir.20000.
X-ray crystal structure analysis was performed on single crystals of two diastereomeric enantiopure quinuclidines, (3R,8R)-3-vinyl-8-hydroxymethyl-quinuclidine (quincoridine, QCD) and (3R,8S)-3-vinyl-8-hydroxymethyl-quinuclidine (quincorine, QCI) as their salts with tartaric and p-toluenesulphonate anions, respectively. The molecules of these quinuclidine derivatives are considered here as fragments of the Cinchona alkaloids, quinidine and quinine. A comparison of the conformational features of QCD, QCI, and Cinchona alkaloids in the crystalline state shows that the molecular geometry of the title compounds is similar to that of threo-alkaloids (e.g., R,R isomer of epicinchonine) rather than to quinidine and quinine. The packing of the molecules in both structures is dominated by intermolecular hydrogen bonds.
对两种非对映体对映纯奎宁环（(3R,8R)-3-乙烯基-8-羟甲基奎宁环（奎可立定，QCD）和(3R,8S)-3-乙烯基-8-羟甲基奎宁环（奎可林，QCI））的单晶进行了X射线晶体结构分析，它们分别以酒石酸根和对甲苯磺酸根阴离子盐的形式存在。这些奎宁环衍生物的分子在这里被视为金鸡纳生物碱奎尼丁和奎宁的片段。对QCD、QCI和金鸡纳生物碱在晶体状态下的构象特征进行比较表明，标题化合物的分子几何形状与苏式生物碱（例如，表辛可宁的R,R异构体）相似，而不是与奎尼丁和奎宁相似。两种结构中分子的堆积都以分子间氢键为主。
