Synthesis and Solid-State Dynamics of a Crystalline Steroid Molecular Rotor without the Alkyne Axle: Steroid Dimers Based on a 1,4-Di(1,3-dioxan-2-yl)benzene Moiety
- 2 July 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 85 (13), 8501-8509
- https://doi.org/10.1021/acs.joc.0c00867
Abstract
Two diastereomeric crystalline steroid dimers were obtained by acid-catalyzed double acetalization of (20S)-5 alpha-apregnan-3 beta,16 beta,20-triol 3-monoacetate with terephtalaldehyde. These compounds were characterized by NMR in solution, MS, single-crystal X-ray diffraction, and variable-temperature solid-state NMR by C-13 cross-polarization magic angle spinning (CPMAS). While the phenylene rotator in the SR diastereomer remains static even at 373 K, the RR isomer shows a slow rotational process of the phenylene ring at temperatures above room temperature and thus may be considered the first crystalline steroid molecular rotor without the alkyne axle.Funding Information
- Direcci?n General de Asuntos del Personal Acad?mico, Universidad Nacional Aut?noma de M?xico (PAPIIT-IN209119, PAPIIT-IN218820)
- Consejo Nacional de Ciencia y Tecnolog?a (A1-S-8019)
- Facultad de Qu?mica, Universidad Nacional Aut?noma de M?xico (PAIP-5000-9063)
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