On August 15, 2019, De Vylder, Anton; Lauwaert, Jeroen; Sabbe, Maarten K.; Reyniers, Marie-Francoise; De Clercq, Jeriffa; Van Der Voort, Pascal; Thybaut, Joris W. published an article.Synthetic Route of 79815-20-6 The title of the article was Rational design of nucleophilic amine sites via computational probing of steric and electronic effects. And the article contained the following:
Accessibility of the nucleophilic site in organocatalysts is essential to ensure adequate catalytic activity. Gas-phase trimethylborane (TMB) Lewis basicity and Bronsted proton basicity of several amine based organocatalysts have been calculated using the CBS-QB3 model chem. This TMB basicity scale can, as opposed to the proton basicity scale, account for steric effects encountered in the initial nucleophilic attack of the nitrogen free electron pair on a substrate. Since such a step is the first one in several amine catalyzed reactions, severe steric hindrance of the nucleophilic center would render the catalyst ineffective. Comparing the TMB basicity and proton basicity with the exptl. observed catalytic activity of both homogeneous and heterogeneously supported amine sites found in literature for the aldol reaction of acetone with 4-nitrobenzaldehyde showed that, due to the inclusion of these steric effects, the TMB basicity scale is a much better predictor of catalytic activity than the proton basicity. According to this computational Lewis basicity scale, potential steric hindrance in alternative nitrogen containing active sites was probed. This resulted in 3-propylpyrrolidine being proposed among the most promising monofunctional amine groups and 1-(methylamino)propan-2-ol among the most promising bifunctional amine-hydroxyl groups for heterogeneous aldol reaction catalysts. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Synthetic Route of 79815-20-6
The Article related to trimethylborane basicity amine organocatalyst bronsted proton basicity aldol condensation, Physical Organic Chemistry: Addition, Elimination, and Substitution Reactions and other aspects.Synthetic Route of 79815-20-6
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Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles