24647-29-8

Basic information

• Product Name: 2-Azabicyclo[2.2.1]heptan-3-one
• Synonyms: 2-Azabicyclo[2.2.1]heptan-3-one;2-Azanorbornan-3-one
• CAS NO: 24647-29-8
• Molecular Formula: C6H9NO
• Molecular Weight: 111.14176
• Mol File: 24647-29-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 69-74℃
• Boiling Point: 290℃
• Flash Point: 161℃
• Appearance: /
• Density: 1.137
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.509
• PKA: 16.63±0.20(Predicted)
• 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(24647-29-8)
• EPA Substance Registry System: 2-Azabicyclo[2.2.1]heptan-3-one(24647-29-8)

Safety Data

• Hazardous Substances Data: 24647-29-8(Hazardous Substances Data)

Usage

General Description

2-Azabicyclo[2.2.1]heptan-3-one, also known as 3-azabicyclo[2.2.1]heptan-3-one or 3-oxo-1-azabicyclo[2.2.1]heptane, is a heterocyclic compound with a bicyclic structure containing a nitrogen atom. It is a six-membered ring compound with a ketone functional group, making it a cyclic ketone. This chemical is commonly used as a building block in the synthesis of various pharmaceutical compounds and organic molecules. It has applications in the production of drugs, agrochemicals, and other fine chemicals. The compound's unique structure and reactivity make it a valuable intermediate in organic synthesis. Additionally, 2-Azabicyclo[2.2.1]heptan-3-one has potential biological activities and may have use in medicinal and pharmaceutical research.

InChI:InChI=1/C6H9NO/c8-6-4-1-2-5(3-4)7-6/h4-5H,1-3H2,(H,7,8)

Upstream product

• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 

Downstream Products

• 279-24-3 2-aza-bicyclo[2.2.1]heptane 
• 1203306-05-1 cis-3-aminocyclopentanecarboxylic acid hydrochloride 
• 161660-94-2 (1R,3S)-3-((tert-butoxycarbonyl)amino)cyclopentane-1-carboxylic acid 
• 344350-86-3 2-(Benzoyloxy)-<3,3-D2>-2-azabicyclo<2.2.1>heptan 
• 85689-07-2 2-(4-Methylphenylsulfonyl)-2-azabicyclo<2.2.1>heptan 
• 85689-06-1 2exo-(Benzoyloxy)-2-azabicyclo<2.2.1>heptan 
• 85689-06-1 endo-2-(Benzoyloxy)-2-azabicyclo<2.2.1>heptan 
• 167417-45-0 2-carbamoyl-2-azabicyclo<2.2.1>heptan-3-one 
• 625108-11-4 C₇H₁₃NO₂ 
• 167081-32-5 3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester 
• 71830-07-4 (1S,3R)-3-aminocyclopentanecarboxylic acid 
• 134003-03-5 (+)-2-Azabicyclo<2.2.1>heptan-3-one 
• 134003-02-4 (-)-2-Azabicyclo<2.2.1>heptan-3-one 
• 71830-08-5 (1R,3S)-3-aminocyclopentanecarboxylic acid 

Relevant articles and documents

Synthesis of cyclic γ-amino acids for foldamers and peptide nanotubes

Cyclic γ-amino acids are molecular building blocks of great interest in peptide and foldamer chemistry, as they allow the preparation of new structures that are not found in Nature. In this paper, we describe the synthesis of cyclic γ-amino acids that have a cis relationship between the amino and the carboxylic acid groups. This arrangement, in most cases, induces the resulting peptides to adopt a flat conformation, which makes them appropriate for the design of foldamers that adopt β-sheet-type structures. We describe the synthesis of cyclic γ-amino acids that have a cis relationship between the amino and the carboxylic acid groups. This makes them suitable for the design of foldamers that adopt β-sheet-type structures.

HETEROCYCLIC CYCLOPENTYL TETRAHYDROISOQUINOLINE AND TETRAHYDROPYRIDOPYRIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

The present invention is directed to compounds of formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, X, n and the broken lines are as defined herein which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.

Nitrenium and Carbenium Ions in Rearrangements of 2-Azabicyclic Systems

An ionic mechanism proceeding in intimate ion pairs is suggested for the rearrangement of N-sulfonyloxy derivatives of 2-azabicycloheptane and -hept-5-ene (e. g. 9, 11 -> 10, 12). 1.Experiments with 18O labelled educts show partial scrambling dependend both on structure of educt and solvent. 2.In methanol the intermediate carbenium ions (19, 23) react to give methoxy compounds. 3.MINDO/3-calculations are in agreement with the experiments: a) In the saturated systems the nitrenium ion 20 is a stable intermediate. b) The optimized geometries of the rearranged carbenium ions (21, 23) are consistent with the products obtained in methanol.