Enantioselective Approach for Expanding the Three-Dimensional Space of Tetrahydroquinoline to Develop BET Bromodomain Inhibitors was written by Lespinasse, Marie-Ange;Wei, Kaiyao;Perrin, Justine;Winkler, Matthias;Hamaidia, Sieme;Leroy, Alexis;Macek Jilkova, Zuzana;Philouze, Christian;Marche, Patrice N.;Petosa, Carlo;Govin, Jerome;Emadali, Anouk;Wong, Yung-Sing. And the article was included in Chemistry – A European Journal.Electric Literature of C10H20O This article mentions the following:
The pharmaceutical industry has a pervasive need for chiral specific mols. with optimal affinity for their biol. targets. However, the mass production of such compounds is currently limited by conventional chem. routes, that are costly and have an environmental impact. Here, the authors propose easy access to obtain new tetrahydroquinolines, a motif found in many bioactive compounds, that is rapid and cost effective. Starting from simple raw materials, the procedure uses a proline-catalyzed Mannich reaction followed by the addition of BF3·OEt2, which generates a highly electrophilic aza-ortho-quinone methide intermediate capable of reacting with different nucleophiles to form the diversely functionalized tetrahydroquinoline. Moreover, this enantioselective one-pot process provides access for the first time to tetrahydroquinolines with a cis-2,3 and trans-3,4 configuration. As proof of concept, the authors demonstrate that a three-step reaction sequence, from simple and inexpensive starting compounds and catalysts, can generate a BD2-selective BET bromodomain inhibitor with anti-inflammatory effect. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Electric Literature of C10H20O).
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) belongs to alcohols. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Electric Literature of C10H20O
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts