138816-37-2

Basic information

• Product Name: trans-4-methyl-5-phenylpyrrolidin-2-one
• Synonyms: trans-4-methyl-5-phenylpyrrolidin-2-one
• CAS NO: 138816-37-2
• Molecular Weight: 175.23
• Mol File: 138816-37-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: trans-4-methyl-5-phenylpyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-4-methyl-5-phenylpyrrolidin-2-one(138816-37-2)
• EPA Substance Registry System: trans-4-methyl-5-phenylpyrrolidin-2-one(138816-37-2)

Safety Data

• Hazardous Substances Data: 138816-37-2(Hazardous Substances Data)

Upstream product

• 7315-69-7 3-methyl-4-phenyl-butyryl chloride 
• 7315-68-6 3-methyl-4-phenylbutanoic acid 
• 59874-90-7 N-<1-(1-phenylprop-2-enyl)> trichloroacetamide 
• 138816-23-6 (4S,5S)-3,3-Dichloro-4-chloromethyl-5-phenyl-pyrrolidin-2-one 

Relevant articles and documents

Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for γ-Lactam Formation

Described herein is the development of a new entry of acylnitrenoid precursors for γ-lactam synthesis via an intramolecular C-H amidation reaction. Upon Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N-O bond cleavage is facilitated by the chelation of countercations. This protocol offers a convenient and step-economic route to γ-lactams starting from the corresponding carboxylic acids.

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Intramolecular insertion of met al nitrenes into carbon-hydrogen bonds to form γ-lactam rings has traditionally been hindered by competing isocyanate formation. We report the application of theory and mechanism studies to optimize a class of pentamethylcyclopentadienyl iridium(III) catalysts for suppression of this competing pathway. Modulation of the stereoelectronic properties of the auxiliary bidentate ligands to be more electron-donating was suggested by density functional theory calculations to lower the C-H insertion barrier favoring the desired reaction. These catalysts transform a wide range of 1,4,2-dioxazol-5-ones, carbonylnitrene precursors easily accessible from carboxylic acids, into the corresponding γ-lactams via sp3 and sp2 C-H amidation with exceptional selectivity. The power of this method was further demonstrated by the successful late-stage functionalization of amino acid derivatives and other bioactive molecules.