Conformational Study of 9-Dehydro-9-Trifluoromethyl Cinchona Alkaloids via 19F NMR Spectroscopy: Emergence of Trifluoromethyl Moiety as a Conformational Stabilizer and a Probe
| Autor: | George A. Olah, Chuanfa Ni, G. K. Surya Prakash, Jingguo Shen, Andrei K. Yudin, Thomas Mathew, Ralf Haiges, Fang Wang |
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| Rok vydání: | 2011 |
| Předmět: |
Models
Molecular Quinidine Magnetic Resonance Spectroscopy Trifluoromethyl Hydrocarbons Fluorinated Stereochemistry Cinchona Alkaloids Molecular Conformation Substituent General Chemistry Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Deuterium chemistry medicine Moiety Conformational isomerism medicine.drug Stabilizer (chemistry) |
| Zdroj: | Journal of the American Chemical Society. 133:9992-9995 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja202373d |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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