Name: 1-(4-Chlorophenyl)pyrrolidin-2-one. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 1-(4-Chlorophenyl)pyrrolidin-2-one, is researched, Molecular C10H10ClNO, CAS is 7661-33-8, about Late-stage oxidative C(sp3)-H methylation. Author is Feng, Kaibo; Quevedo, Raundi E.; Kohrt, Jeffrey T.; Oderinde, Martins S.; Reilly, Usa; White, M. Christina.
Frequently referred to as the ‘magic Me effect’, the installation of Me groups-especially adjacent (α) to heteroatoms-has been shown to dramatically increase the potency of biol. active mols.1-3. However, existing methylation methods show limited scope and have not been demonstrated in complex settings1. Here, we report a regioselective and chemoselective oxidative C(sp3)-H methylation method that is compatible with late-stage functionalization of drug scaffolds and natural products. This combines a highly site-selective and chemoselective C-H hydroxylation with a mild, functional-group-tolerant methylation. Using a small-mol. manganese catalyst, Mn(CF3PDP), at low loading (at a substrate/catalyst ratio of 200) affords targeted C-H hydroxylation on heterocyclic cores, while preserving electron-neutral and electron-rich aryls. Fluorine- or Lewis-acid-assisted formation of reactive iminium or oxonium intermediates enables the use of a mildly nucleophilic organoaluminum methylating reagent that preserves other electrophilic functionalities on the substrate. We show this late-stage C(sp3)-H methylation on 41 substrates housing 16 different medicinally important cores that include electron-rich aryls, heterocycles, carbonyls and amines. Eighteen pharmacol. relevant mols. with competing sites, including drugs (for example, tedizolid) and natural products, are methylated site-selectively at the most electron rich, least sterically hindered position. We demonstrate the syntheses of two magic Me substrates, an inverse agonist for the nuclear receptor RORc and an antagonist of the sphingosine-1-phosphate receptor-1, via late-stage methylation from the drug or its advanced precursor. We also show a remote methylation of the B-ring carbocycle of an abiraterone analog. The ability to methylate such complex mols. at late stages will reduce synthetic effort and thereby expedite broader exploration of the magic Me effect in pursuit of new small-mol. therapeutics and chem. probes.
There is still a lot of research devoted to this compound(SMILES：O=C1N(C2=CC=C(Cl)C=C2)CCC1)Name: 1-(4-Chlorophenyl)pyrrolidin-2-one, and with the development of science, more effects of this compound(7661-33-8) can be discovered.
Reference:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts