226991-18-0

Basic information

• Product Name: (5S)-5-(phenylMethyl)-2-Pyrrolidinone
• Synonyms: (5S)-5-(phenylMethyl)-2-Pyrrolidinone
• CAS NO: 226991-18-0
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.22702
• Mol File: 226991-18-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 57-58℃ (ethyl ether )
• Appearance: /
• CAS DataBase Reference: (5S)-5-(phenylMethyl)-2-Pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-(phenylMethyl)-2-Pyrrolidinone(226991-18-0)
• EPA Substance Registry System: (5S)-5-(phenylMethyl)-2-Pyrrolidinone(226991-18-0)

Safety Data

• Hazardous Substances Data: 226991-18-0(Hazardous Substances Data)

Usage

General Description

The chemical compound (5S)-5-(phenylMethyl)-2-Pyrrolidinone, also known as phenylmethyl-2-pyrrolidinone, is a heterocyclic compound with a pyrrolidinone ring and a phenylmethyl side chain. It is classified as a lactam and is commonly used as a precursor in the synthesis of a variety of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a solvent and intermediate in organic synthesis. The compound has a molecular formula of C11H13NO and a molecular weight of 175.23 g/mol. Its chemical structure and properties make it a versatile and important compound in organic chemistry.

Upstream product

• 17342-08-4 (S)-Pyroglutaminol 
• 51693-17-5 (S)-toluene-4-sulfonic acid 5-oxo-pyrrolidin-2-ylmethyl ester 
• 591-51-5 phenyllithium 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 2270-20-4 5-Phenylpentanoic acid 
• 606143-35-5 C₁₇H₂₄N₂O₂ 
• 606143-30-0 (E)-(2'S)-5-benzylidene-2'-(methoxymethyl)[1,1']bipyrrolidinyl-2-one 

Downstream Products

• 1419108-62-5 C₂₄H₃₇NO₄Si 
• 1419108-73-8 C₃₀H₃₉NO₄SeSi 
• 1419108-69-2 C₂₄H₃₅NO₄Si 
• 1419108-28-3 C₁₇H₂₅NO₃Si 
• 402955-80-0 (S)-(N-tert-butyloxycarbonyl)-4-amino-5-phenyl-1-pyridin-2-yl-pentan-1-one 
• 402955-78-6 (S)-N-t-butoxycarbonyl-5-benzyl-2-pyrrolidinone 
• 97522-31-1 (+)-2-(S)-benzylpyrrolidine 

Relevant articles and documents

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

Iridium-Catalyzed Enantioselective C(sp3)-H Amidation Controlled by Attractive Noncovalent Interactions

While remarkable progress has been made over the past decade, new design strategies for chiral catalysts in enantioselective C(sp3)-H functionalization reactions are still highly desirable. In particular, the ability to use attractive noncovalent interactions for rate acceleration and enantiocontrol would significantly expand the current arsenal for asymmetric metal catalysis. Herein, we report the development of a highly enantioselective Ir(III)-catalyzed intramolecular C(sp3)-H amidation reaction of dioxazolone substrates for synthesis of optically enriched γ-lactams using a newly designed α-amino-acid-based chiral ligand. This Ir-catalyzed reaction proceeds with excellent efficiency and with outstanding enantioselectivity for both activated and unactivated alkyl C(sp3)-H bonds under very mild conditions. It offers the first general route for asymmetric synthesis of γ-alkyl γ-lactams. Water was found to be a unique cosolvent to achieve excellent enantioselectivity for γ-aryl lactam production. Mechanistic studies revealed that the ligands form a well-defined groove-type chiral pocket around the Ir center. The hydrophobic effect of this pocket allows facile stereocontrolled binding of substrates in polar or aqueous media. Instead of capitalizing on steric repulsions as in the conventional approaches, this new Ir catalyst operates through an unprecedented enantiocontrol mechanism for intramolecular nitrenoid C-H insertion featuring multiple attractive noncovalent interactions.

A practical photochemically induced method for nin bond cleavage of n,n-disubstituted hydrazides

The development of an unprecedented methodology based upon direct photolysis of N,N-disubstituted hydrazides to secure N-N bond cleavage and to trigger the formation of NH-free lactams has been disclosed.