Synthesis, structure of 7-oxa-1-azabicyclo[2.2.1]heptane derivative obtained from sugar nitrone and analysis of its conformational variety
| Autor: | Ewa Mironiuk-Puchalska, Izabela D. Madura, Paulina H. Marek, Tomasz Rowicki, Wojciech Sas, Karolina Kopczyńska |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Heptane 010405 organic chemistry Organic Chemistry Crystal structure 010402 general chemistry 01 natural sciences Cycloaddition 0104 chemical sciences Analytical Chemistry Nitrone Inorganic Chemistry Crystallography chemistry.chemical_compound Molecular geometry chemistry Intramolecular force Molecule Spectroscopy Derivative (chemistry) |
| Zdroj: | Journal of Molecular Structure. 1183:14-23 |
| ISSN: | 0022-2860 |
| DOI: | 10.1016/j.molstruc.2019.01.058 |
| Popis: | Dispiro derivative of 7-oxa-1-azabicyclo [2.2.1]heptane 5 was synthesized as a single stereoisomer from N-(5-allyl-spiro [1,3-dioxan-2,1′-cyclohexane]-5-yl)hydroxylamine 2 and protected d -mannose 3, through intramolecular 1,3-dipolar cycloaddition of in situ formed N-(but-3-en-1-yl)nitrone 4. Structure of product 5 was attributed on the basis of NMR and X-ray analyses. In the solid state, three crystallographically independent molecules of 5 were detected, every exhibiting a different orientation of spiro connected rings. Conformational analysis performed by DFT calculations in the gas phase was performed and revealed that the conformations observed in the crystal correspond to the most stable molecular geometries. Two of them were also found to be dominant in solution. |
| Databáze: | OpenAIRE |
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