Palladium-Catalyzed Generation of ortho-Quinone Methides. A Three-Component Synthesis of L-Shaped Dimeric Steroidal Scaffolds
- 17 February 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 86 (5), 4112-4120
- https://doi.org/10.1021/acs.joc.0c02943
Abstract
A series of hybrid dimers having orthogonal steroidal cores bridged by a chroman ketal moiety were obtained by Pd-catalyzed three-component reactions of steroid alkynols, 2-formylestradiol 17-monoacetate, and methyl orthoformate, via ortho-quinone methide intermediates. One of the obtained L-shaped scaffolds showed an inefficient crystal packing featuring large channels within the crystal array. Monte Carlo simulations indicate that these voids preferentially allocate n-hexane, opening the way to explore further applications of similar organic crystalline materials as selective hosts for small molecules.Keywords
Funding Information
- Direcci?n General de Asuntos del Personal Acad?mico, Universidad Nacional Aut?noma de M?xico (DGAPA-IN218820)
- Consejo Nacional de Ciencia y Tecnolog?a (0185183, A1-S-8019)
- IT4Innovations National Supercomputing Center (LM2015070)
This publication has 33 references indexed in Scilit:
- 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 MoietyThe Journal of Organic Chemistry, 2020
- The Chemistry of Porous Organic Molecular MaterialsAdvanced Functional Materials, 2020
- Synthesis of Dimeric Steroid Trioxabispiroacetals Scaffolds by Gold(I)‐Catalyzed Hydroalkoxylation–Hydration of DiynediolsEuropean Journal of Organic Chemistry, 2019
- Synthesis, Characterization, and Solid State Dynamic Studies of a Hydrogen Bond-Hindered Steroidal Molecular Rotor with a Flexible AxisThe Journal of Organic Chemistry, 2018
- Organic Molecules with Porous Crystal StructuresSynlett, 2016
- Synthesis, NMR and crystal characterization of dimeric terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-olsSteroids, 2016
- Tunable Porous Organic Crystals: Structural Scope and Adsorption Properties of Nanoporous Steroidal UreasJournal of the American Chemical Society, 2013
- Bile Acid Scaffolds in Supramolecular Chemistry: The Interplay of Design and SynthesisMolecules, 2007
- Bile Acids as Building Blocks of Supramolecular HostsMolecules, 2001
- Cholaphanes et al.; steroids as structural components in molecular engineeringChemical Society Reviews, 1993