924272-78-6

Basic information

• Product Name: (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE
• Synonyms: (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE
• CAS NO: 924272-78-6
• Molecular Formula: C8H9NO
• Molecular Weight: 135.16
• Mol File: 924272-78-6.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE(924272-78-6)
• EPA Substance Registry System: (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE(924272-78-6)

Safety Data

• Hazardous Substances Data: 924272-78-6(Hazardous Substances Data)

Usage

Description

(1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE is a carbocyclic β-lactam, a type of organic compound that is structurally similar to β-lactam antibiotics. It is characterized by its unique stereochemistry, with four chiral centers at the 1, 2, 5, and 6 positions, and a ring structure that includes a nitrogen atom. (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE is known for its potential applications in the synthesis of enantiopure carbocyclic β-amino acids and as a starting racemate for the development of new pharmaceuticals.

Uses

Used in Pharmaceutical Industry:
(1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE is used as a starting racemate for the development of 1,4-ethylene-bridged cispentacin, a novel compound with potential therapeutic applications. (1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE serves as a valuable building block in the synthesis of new drugs, contributing to the advancement of pharmaceutical research and development.
Used in Chemical Synthesis:
(1S,2S,5R,6R)-3-AZATRICYCLO[4.2.1.0(2,5)]NON-7-EN-4-ONE is used as a key intermediate in the asymmetric synthesis of enantiopure carbocyclic β-amino acids. This process involves the use of Candida antarctica lipase, an enzyme that catalyzes the solvent-free vapor-assisted enantioselective hydrolytic ring-opening of carbocyclic β-lactams. The resulting enantiopure carbocyclic β-amino acids have potential applications in various fields, including the development of chiral pharmaceuticals and the synthesis of biologically active compounds.

Upstream product

• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 14805-30-2 4-oxo-(1rC⁹,2tH,5tH,6cC⁹)-3-aza-tricyclo[4.2.1.0^2,5]non-7-ene-3-sulfonyl chloride 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 14735-70-7 diexo-3-Aza-4-oxotricyclo<4.2.1.0^2,5>non-7-ene 

Downstream Products

• 1190392-23-4 methyl [6(S)-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-α]]pyrimidine-6-carboxylate 
• 1190709-67-1 methyl (7S)-9-oxo-3,8-diazatetracyclo[9.2.1.0(2,10).0(4,8)]tetradeca-3,12-diene-7-carboxylate 
• 924272-78-6 (1S,2S,5R,6R)-exo-3-azatricyclo[4.2.1.0(2,5)]non-7-en-4-one 
• 924272-78-6 (1R,2R,5S,6S)-3-azatricyclo[4.2.1.0^2,5]non-7-en-4-one 
• 871357-90-3 (1SR,2SR,5RS,6RS)-4-oxo-3-aza-tricyclo[4.2.1.0(2,5)]non-7-ene-3-carboxylic acid tert-butyl ester 
• 104770-18-5 ethyl exo-3-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate hydrochloride 

Relevant articles and documents

Diversity-oriented Functionalization of Cyclodienes Through Selective Cycloaddition/Ring-opening/Cross-metathesis Protocols; Transformation of a “Flatland” into Three-dimensional Scaffolds With Stereo- and Regiocontrol

This article presents selective transformations of some readily available cyclodienes through simple chemical procedures into novel functionalized small-molecular entities. The syntheses hereby described involved selective cycloadditions, followed by ring

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

A process for producing an intermediate agonist GRK 3

The present invention is directed to processes for preparing beta 3 agonists of Formula (I) and Formula (II) and their intermediates. The beta 3 agonists are useful in the treatment of certain disorders, including overactive bladder, urinary incontinence, and urinary urgency.