Loker Hydrocarbon Research Institute, Department of Chemistry, University of Southern California, Los Angeles, California 90089, USA.
J Am Chem Soc. 2011 Jul 6;133(26):9992-5. doi: 10.1021/ja202373d. Epub 2011 Jun 13.
The trifluoromethyl substituent has been incorporated into quinidine as a conformational stabilizer and a probe to provide straightforward insight into the conformational behavior of cinchona alkaloids. By significantly decreasing the rotation rate of the quinoline-carbinol bond, the relatively bulky CF(3) group enables the NMR signals of the syn and anti conformers to be differentiated at room temperature. In addition to the stabilizing effect, the introduction of the fluorinated moiety also facilitates the application of (19)F NMR spectroscopy, thereby allowing conformational studies under various conditions without the use of deuterated solvents.
三氟甲基取代基被引入奎宁中作为构象稳定剂和探针，以提供对金鸡纳生物碱构象行为的直接洞察。通过显著降低喹啉-甲醇键的旋转速率，相对较大的 CF(3)基团能够在室温下区分顺式和反式构象的 NMR 信号。除了稳定化效应外，引入氟化部分还方便了 (19)F NMR 光谱的应用，从而允许在不使用氘代溶剂的情况下在各种条件下进行构象研究。
