24571-99-1

Usage

Uses

Used in Organic Synthesis:
(6Z)-9-azabicyclo[6.2.0]dec-6-en-10-one is used as a building block in organic synthesis for the preparation of a wide range of compounds with diverse applications. Its unique structure and reactivity allow for the creation of complex molecules with specific properties.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (6Z)-9-azabicyclo[6.2.0]dec-6-en-10-one is utilized as a key intermediate for the development of pharmaceuticals. Its incorporation into drug candidates can lead to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in Pharmaceutical Production:
(6Z)-9-azabicyclo[6.2.0]dec-6-en-10-one is used as an intermediate in the production of various compounds with important biological and pharmaceutical properties. Its presence in the synthesis process can contribute to the development of novel drugs with potential applications in treating various diseases and medical conditions.
Used in Research and Development:
(6Z)-9-azabicyclo[6.2.0]dec-6-en-10-one is also employed in research and development settings, where it serves as a valuable tool for understanding the structure-activity relationships of biologically active molecules. Its unique properties can help researchers identify new targets and design more effective drugs for various therapeutic areas.

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 3806-59-5 1,3-cyclooctadiene 

Downstream Products

• 522644-10-6 (1R,2S)-2-Amino-cyclooctanecarboxylic acid; hydrochloride 

Relevant academic research and scientific papers

Synthesis and Evaluation of Novel Ring-Strained Noncanonical Amino Acids for Residue-Specific Bioorthogonal Reactions in Living Cells

Bioorthogonal reactions are ideally suited to selectively modify proteins in complex environments, even in vivo. Kinetics and product stability of these reactions are crucial parameters to evaluate their usefulness for specific applications. Strain promoted inverse electron demand Diels–Alder cycloadditions (SPIEDAC) between tetrazines and strained alkenes or alkynes are particularly popular, as they allow ultrafast labeling inside cells. In combination with genetic code expansion (GCE)-a method that allows to incorporate noncanonical amino acids (ncAAs) site-specifically into proteins in vivo. These reactions enable residue-specific fluorophore attachment to proteins in living mammalian cells. Several SPIEDAC capable ncAAs have been presented and studied under diverse conditions, revealing different instabilities ranging from educt decomposition to product loss due to β-elimination. To identify which compounds yield the best labeling inside living mammalian cells has frequently been difficult. In this study we present a) the synthesis of four new SPIEDAC reactive ncAAs that cannot undergo β-elimination and b) a fluorescence flow cytometry based FRET-assay to measure reaction kinetics inside living cells. Our results, which at first sight can be seen conflicting with some other studies, capture GCE-specific experimental conditions, such as long-term exposure of the ring-strained ncAA to living cells, that are not taken into account in other assays.

Efficient enzymatic routes for the synthesis of new eight-membered cyclic β-amino acid and β-lactam enantiomers

Efficient enzymatic resolutions are reported for the preparation of new eight-membered ring-fused enantiomeric β-amino acids [(1R, 2S)-9 and (1S, 2R)-9] and β-lactams [(1S, 8R)-3, (1R, 8S)-3 (1S, 8R)-4 and (1R, 8S)-7], through asymmetric acylation of (±)-4 (E > 100) or enantioselective hydrolysis (E > 200) of the corresponding inactivated (±)-3 or activated (±)-4 β-lactams, catalyzed by PSIM or CAL-B in an organic solvent. CAL-B-catalyzed ring cleavage of (±)-6 (E > 200) resulted in the unreacted (1S, 8R)-6, potential intermediate for the synthesis of enantiomeric anatoxin-a. The best strategies, in view of E, reaction rate and product yields, which underline the importance of substrate engineering, are highlighted.