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- Title
Expected and Unexpected Products in Half Curcuminoid Synthesis: Crystal Structures of But-3-en-2-ones and 3-Methylcyclohex-2-enones.
- Authors
Obregón-Mendoza, Marco A.; Arias-Olguín, Imilla I.; Meza-Morales, William; Alvarez-Ricardo, Yair; Chávez, María Isabel; Toscano, Rubén A.; Cassani, Julia; Enríquez, Raúl G.
- Abstract
The expected (E)-but-3-en-2-ones compounds I and II (half curcuminoids) were obtained by the Claisen–Schmidt reaction between aldehydes 3,4-dimethoxybenzaldehyde or 4-nitrobenzaldehyde with acetone. Concomitantly, 3-methylcyclohex-2-enones compounds III and IV arose from an unexpected reaction of but-3-en-2-ones in the cascade reaction of a Michael-type addition of a second molecule of acetone followed by Robinson annulation under strong basic conditions. Both enones exhibit the (E)-configuration, compound I displays s-trans conformation, whereas compound II exhibits conformational disorder as solid solution of s-cis and s-trans conformations. The related 3-methylcyclohex-2-enones exhibit envelope conformation. Compound III constitutes an example of the rarest case of racemic solid solution (pseudoracemate), where a lack of chiral discrimination with respect to the two enantiomers leads to an enantiomeric disorder of a racemic mixture with different occupancies at the reference site. Due to the lack of strong hydrogen-bond donors in all compounds, the crystal packing is mainly stabilized by weak intermolecular C-H···O interactions between the molecules. The present work provides a new perspective on the search for by-products normally overlooked in Claisen–Schmidt condensations.
- Subjects
CRYSTAL structure; SOLID solutions; ADDITION reactions; CARBONYL compounds; MICHAEL reaction; RACEMIC mixtures; ACETONE; RESOLUTION (Chemistry)
- Publication
Crystals (2073-4352), 2021, Vol 11, Issue 4, p404
- ISSN
2073-4352
- Publication type
Article
- DOI
10.3390/cryst11040404