56553-09-4

Basic information

• Product Name: (5S)-5-phenyl-2-Pyrrolidinone
• Synonyms: (5S)-5-phenyl-2-Pyrrolidinone
• CAS NO: 56553-09-4
• Molecular Formula: C10H11NO
• Molecular Weight: 161.203
• Mol File: 56553-09-4.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: (5S)-5-phenyl-2-Pyrrolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-phenyl-2-Pyrrolidinone(56553-09-4)
• EPA Substance Registry System: (5S)-5-phenyl-2-Pyrrolidinone(56553-09-4)

Safety Data

• Hazardous Substances Data: 56553-09-4(Hazardous Substances Data)

Usage

Description

(5S)-5-phenyl-2-Pyrrolidinone, with the molecular formula C10H11NO, is a chemical compound featuring a five-membered lactam ring to which a phenyl group is attached at the 5-position. This versatile compound is a significant component in the realm of organic chemistry and drug discovery, known for its potential biological activities and therapeutic properties.

Uses

Used in Pharmaceutical Research:
(5S)-5-phenyl-2-Pyrrolidinone is used as a building block in the pharmaceutical industry for the development of new drugs. Its unique structure allows it to serve as a precursor in the production of various pharmaceuticals, contributing to the advancement of medical treatments.
Used in Agrochemical Production:
In the agrochemical industry, (5S)-5-phenyl-2-Pyrrolidinone is utilized as a starting material for the synthesis of different agrochemicals. Its application aids in the creation of compounds that can be used in the agricultural sector for pest control and crop protection.
Used in Organic Synthesis:
(5S)-5-phenyl-2-Pyrrolidinone is employed as a key component in the synthesis of a wide array of organic compounds. Its presence in these reactions enables the production of diverse chemical entities, expanding the scope of organic chemistry.
Used in Biological Activity Studies:
(5S)-5-phenyl-2-Pyrrolidinone is also studied for its potential biological activities, which may lead to the discovery of new therapeutic properties. This research could pave the way for the development of novel treatments for various medical conditions.

Upstream product

• 1294455-04-1 (5S)-1-[(1R)-2-chloro-1-phenylethyl]-5-phenyl-2-pyrrolidone 
• 1294455-05-2 (S)-5-phenyl-1-(1-phenylvinyl)-2-pyrrolidone 
• 132959-39-8 (-)-(3R,7aR)-3-Phenyl-5-oxo-7a-phenyl-2,3,5,6,7,7a-hexahydropyrrolo<2,1-b>oxazole 
• 2051-95-8 succinylbenzene 
• 1821-12-1 4-Phenylbutyric acid 
• 18496-54-3 phenylbutyric acid chloride 
• 32153-46-1 4-PBHA 
• 23132-29-8 4-oxo-4-phenylbutanamide 
• 55666-45-0 4-oxo-4-phenyl-butyric acid tert-butyl ester 
• 104750-69-8 isopropyl 4-phenyl-4-oxobutanoate 
• 6270-17-3 ethyl 3-benzoylpropanoate 
• 75-89-8 2,2,2-trifluoroethanol 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 
• 25333-24-8 3-benzoylpropionic acid methyl ester 

Downstream Products

• 23132-29-8 4-oxo-4-phenylbutanamide 
• 1006-64-0 (S)-2-phenylpyrrolidine 
• 1417575-45-1 C₁₃H₁₅NO₂ 
• 938-36-3 (S)-(-)-1-methyl-2-phenylpyrrolidine 

Relevant articles and documents

Method for synthesizing chiral lactam through tandem reductive amination

The invention belongs to the technical field of chemical synthesis preparation, and particularly relates to a method for synthesizing chiral lactam through tandem reductive amination, which successfully realizes ruthenium-catalyzed asymmetric reductive amination/cyclization tandem reaction to efficiently construct chiral lactam by using substrates of keto acid and keto ester.

RETRACTED ARTICLE: Site-selective enzymatic C-H amidation for synthesis of diverse lactams

A major challenge in carbon?hydrogen (C?H) bond functionalization is to have the catalyst control precisely where a reaction takes place. In this study, we report engineered cytochrome P450 enzymes that perform unprecedented enantioselective C?H amidation reactions and control the site selectivity to divergently construct b-, g-, and d-lactams, completely overruling the inherent reactivities of the C?H bonds. The enzymes, expressed in Escherichia coli cells, accomplish this abiological carbon?nitrogen bond formation via reactive iron-bound carbonyl nitrenes generated from nature-inspired acyl-protected hydroxamate precursors. This transformation is exceptionally efficient (up to 1,020,000 total turnovers) and selective (up to 25:1 regioselectivity and 97%, please refer to compound 2v enantiomeric excess), and can be performed easily on preparative scale.

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.