123632-31-5

Basic information

• Product Name: 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4S)-
• Synonyms: (S)-3-(4-chlorophenyl)-2-pyrrolidone;(S)-4-(4-Chloro-phenyl)-pyrrolidin-2-one;(+)-4-(4-chloro-phenyl)-pyrrolidin-2-one;(S)-4-(4-chlorophenyl)-2-pyrrolidone;(S)-4-(4-chlorophenyl)pyrrolidin-2-one;(S)-4-(4-chlorphenyl)pyrrolidin-2-one
• CAS NO: 123632-31-5
• Molecular Formula: C10H10ClNO
• Molecular Weight: 195.648
• Mol File: 123632-31-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4S)-(123632-31-5)
• EPA Substance Registry System: 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4S)-(123632-31-5)

Safety Data

• Hazardous Substances Data: 123632-31-5(Hazardous Substances Data)

Usage

General Description

2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4S)- is a chemical compound with a molecular formula C10H10ClNO. It is a white to pale yellow solid, soluble in water and most organic solvents. 2-Pyrrolidinone, 4-(4-chlorophenyl)-, (4S)- is a derivative of pyrrolidinone and is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It has been found to have potential applications in the field of medicine and is used in the production of various drugs, including anti-inflammatory and antifungal agents. Additionally, it has been studied for its potential antitumor and antiviral properties.

Upstream product

• 1006386-92-0 ethyl (2S,3S)-2-bromo-3-hydroxy-3-(4-chlorophenyl)propanoate 
• 1006386-91-9 (4R,5S)-4-carbethoxy-5-(4-chlorophenyl)-1,3,2-dioxathiolane 2-oxide 
• 894421-57-9 (Z)-ethyl 4-azido-3-(4-chlorophenyl)but-2-enoate 
• 537676-64-5 ethyl 4-azido-3-(4-chlorophenyl)-2-butenoate 
• 537676-63-4 ethyl (3R)-3-cyano-3-(4-chlorophenyl)propanoate 
• 363152-43-6 (S)-methyl 3-(4-chlorophenyl)-4-nitrobutanoate 
• 321575-57-9 (R)-phenyl 3-(4-chlorophenyl)-4-nitrobutanoate 
• 152714-07-3 3-(4-chlorophenyl)cyclobutanone 
• 1073-67-2 4-vinylbenzyl chloride 
• 52927-44-3 dimethyl 2-(4-chlorobenzylidene)malonate 
• 360072-54-4 methyl 2-carbomethoxy-4-nitro-3-(4-chloro-phenyl)-butyrate 
• 1075-77-0 4-chlorocinnamaldehyde 
• 948017-83-2 C₁₁H₁₄ClNO₂ 
• 1001058-66-7 (S)-3-(4-chlorophenyl)-4-nitrobutyraldehyde 

Downstream Products

• 63701-56-4 (+)-Baclofen hydrochloride 

Relevant articles and documents

Desymmetrization of Prochiral Cyclobutanones via Nitrogen Insertion: A Concise Route to Chiral γ-Lactams

Asymmetric access to γ-lactams is achieved via a cyclobutanone ring expansion using widely available (1S,2R)-1-amino-2-indanol for chiral induction. Mechanistic analysis of the key N,O-ketal rearrangement reveals a Curtin–Hammett scenario, which enables a downstream stereoinduction (up to 88:12 dr) and is corroborated by spectroscopic, crystallographic, and computational studies. In combination with an easy deprotection protocol, this operationally simple sequence allows the synthesis of a range of optically pure γ-lactams, including those bearing all-carbon quaternary stereocenters. In addition, the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin further demonstrates the synthetic utility and highlights the general applicability of the presented method.

Efficient synthesis of β-aryl-γ-lactams and their resolution with (S)-Naproxen: Preparation of (R)- and (S)-Baclofen

An efficient synthesis of enantiomerically-pure β-aryl-γ-lactams is described. The principal feature of this synthesis is the practical resolution of β-aryl-γ-lactams with (S)-Naproxen. The procedure is based on the Michael addition of nitromethane to benzylidenemalonates, which was easily obtained, followed by the reduction of the γ-nitroester in the presence of Raney nickel and the subsequent saponification/decarboxylation reaction. The utility of this methodology was highlighted by the preparation of enantiomerically-pure (R)- and (S)-Baclofen hydrochloride.

Asymmetric synthesis of γ-nitroesters by an organocatalytic one-pot strategy

An enantioselective synthesis of γ-nitroesters by a one-pot asymmetric Michael addition/oxidative esterification of α,β- unsaturated aldehydes is presented. The procedure is based on merging the enantioselective organocatalytic nitroalkane addition with an N-bromosuccinimide-based oxidation. The γ-nitroesters are obtained in good yields and enantioselectivities, and the method provides an attractive entry to optically active γ-aminoesters, 2-piperidones, and 2-pyrrolidones.