2183-99-5

Usage

Chemical compound

2-Azabicyclo[3.2.0]heptan-3-one

Also known as

oxabicyclo[3.2.0]heptan-3-one

Bicyclic structure

Contains a 7-membered ring with a nitrogen atom and a carbonyl group

Use

Commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals

Reactivity

Highly reactive due to the strain in its ring structure, allowing it to participate in various chemical reactions

Applications

Potential applications in the development of new drugs and as a key intermediate in organic chemistry

Value

Unique structure and reactivity make it a valuable compound in chemical synthesis

Upstream product

• 2410-50-6 2-Azabicyclo<3.2.0>hept-6-en-3-on 
• 2183-86-0 1,3-dihydro-2H-azepin-2-one 

Downstream Products

• 327-58-2 2-Azabicyclo<3.2.0>heptan 

Relevant academic research and scientific papers

β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2H-azepin-2-one

The photochemical electrocyclization reaction of the title compound in the presence of β-cyclodextrin was examined in different conditions. No enantioselectivity was observed in solution, but solid-state reactions of a 1:1 complex as a suspension or a thin film, followed by reduction, provided (1R,5R)-2-azabicyclo[3.2.0]heptan-3-one in isolated yields up to 79% and with ee values up to 45%.

Practical syntheses of both enantiomers of the conformationally restricted GABA analogue cis-(2-aminocyclobutyl)acetic acid

Two efficient routes have been established for the preparation of both enantiomers of cis-(2-aminocyclobutyl)acetic acid, a conformationally restricted analogue of GABA. Both procedures converged on the racemic N-tert-butoxycarbonyl derivative of the target compound, which was resolved through chiral derivatization with an oxazolidinone auxiliary, which also allowed determination of the absolute configuration of the new compounds. The first route involved the homologation of cis-2-aminocyclobutanecarboxylic acid, whereas the second route employed an intramolecular photocyclization protocol, which provided an expedient, cisselective access to the lactam form of the target structure.

Regio- and Stereoselectivity in Anionic Ring Opening Reactions of 2-Azabicycloheptane Derivatives

In the regioselective ring opening of 1 via the dianion 1c the intermediacy of 2a is proven by labeling experiments.The regioselective cleavage of the four-membered ring in 3 by LiAlH4 proceeds stereoselectively both in the ring and the side chain positio

Stereoselective Preparation of Bicyclic Lactams by Copper- or Ruthenium-catalysed Cyclization of N-Allyltrichloroacetamides: A Novel Entry to Pyrrolidine Alkaloid Skeletons

Cyclization of certain N-allyltrichloroacetamides provides a stereoselective preparative method for several bicyclic lactams.

Synthesis of &γ-Aminobutyric Acid Analogue of Restricted Conformation. Part 1. The 2-Aminocycloalkylacetic Acids

The syntheses of cis- and trans-2-aminocyclopropyl, -cyclobutyl, -cyclopentyl, and cyclohexylacetic acids as γ-aminobutyric acid analogues of restricted conformation are described.Mass spectral evidence fully supports the stereochemical assignements of configurational isomers.