134003-02-4

Basic information

• Product Name: (-)-2-Azabicyclo<2.2.1>heptan-3-one
• Synonyms: (-)-2-Azabicyclo<2.2.1>heptan-3-one
• CAS NO: 134003-02-4
• Molecular Weight: 111.144
• Mol File: 134003-02-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-2-Azabicyclo<2.2.1>heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2-Azabicyclo<2.2.1>heptan-3-one(134003-02-4)
• EPA Substance Registry System: (-)-2-Azabicyclo<2.2.1>heptan-3-one(134003-02-4)

Safety Data

• Hazardous Substances Data: 134003-02-4(Hazardous Substances Data)

Usage

General Description

(-)-2-Azabicyclo<2.2.1>heptan-3-one, also known as quinoxaline, is a chemical compound with the molecular formula C7H7NO. It is a bicyclic compound with a nitrogen atom, and it is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Its unique structure and reactivity make it a valuable building block for the production of various organic compounds. Quinoxaline derivatives have been studied for their potential biological activities, including antimicrobial, antifungal, and anticancer properties. Additionally, quinoxaline-based compounds have been investigated for their potential use as fluorescent probes and materials in organic electronics. Overall, (-)-2-Azabicyclo<2.2.1>heptan-3-one is a versatile chemical with a wide range of applications in the fields of pharmaceuticals, agriculture, and materials science.

Upstream product

• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 24647-29-8 2-Azabicyclo[2.2.1]heptan-3-one 

Downstream Products

• 1203306-05-1 (1S,3R)-3-aminocyclopentanecarboxylic acid hydrochloride salt 
• 151907-79-8 (1S-cis)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-cyclopentene-1-carboxylic acid 
• 625108-11-4 C₇H₁₃NO₂ 
• 782493-18-9 (1S)-N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-isopropyl-3-oxocyclopentanecarboxamide 
• 782493-13-4 (1S)-1-isopropyl-3-oxocyclopentanecarboxylic acid 
• 624734-28-7 C₂₀H₂₁NO₂ 
• 1263375-29-6 (1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentanecarbaldehyde 
• 1263371-89-6 ((1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentyl)methanol 
• 1110772-11-6 ((1S,3R)-3-aminocyclopentyl)methanol 
• 347185-68-6 tert-butyl ((1R,3S)-3-(hydroxymethyl)cyclopentyl)carbamate 

Relevant articles and documents

Enzymatic method for the synthesis of blockbuster drug intermediates - Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers

A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Identification and application of enantiocomplementary lactamases for Vince lactam derivatives

Four enzymes showing hydrolytic activity on derivatives of 2-azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) were successfully identified through analysis of protein crystal structure and amino acid sequence alignments. Enantiocomplementary activities were observed on Vince lactam and its saturated analog 2-azabicyclo[2.2.1]heptan-3-one with non-heme chloroperoxidase (CPO-T) from Streptomyces aureofaciens, cyclic imide hydrolase (CIH) from Pseudomonas putida, polyamidase (NfpolyA) from Nocardia farcinica, and amidase (AMI) from Rhodococcus globerulus, and perfect kinetic resolution was achieved (E>200). Computational analysis of amide bond resonance stabilization in lactams correlated well with the overall reactivity pattern of the lactams as a function of ring size and strain. The biocatalysts cloned and investigated in this study could be of interest for the synthesis of enantiopure carbocyclic nucleoside analogues.