CAS 866083-42-3

2-Azabicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-

Description:

2-Azabicyclo[3.1.0]hexane-3-carbonitrile, (1S,3S,5S)-, with CAS number 866083-42-3, is a bicyclic organic compound characterized by its unique bicyclic structure that includes a nitrogen atom within the ring system. This compound features a carbonitrile functional group, which is indicative of its potential reactivity and applications in organic synthesis. The stereochemistry of the compound is specified by the (1S,3S,5S) designation, indicating the spatial arrangement of its substituents, which can influence its biological activity and interaction with other molecules. Typically, compounds of this type may exhibit properties such as solubility in polar solvents, and they may participate in various chemical reactions, including nucleophilic additions or substitutions due to the presence of the carbonitrile group. Additionally, the bicyclic structure can impart rigidity, affecting the compound's conformational dynamics and potential applications in medicinal chemistry or as intermediates in synthetic pathways. Overall, this compound represents a fascinating example of bicyclic nitrogen-containing heterocycles in organic chemistry.

Formula: C₆H₈N₂

Synonyms:

• (1S,3S,5S)-2-Azabicyclo[3.1.0]Hexane-3-Carbonitrile

(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carbonitrile

Controlled Product

CAS: 866083-42-3

Applications Saxagliptin hydrochloride monohydrate, an anti-diabetic drug can be synthesized using a coupling reaction of (S)-phthalimido-(3-hydroxy-adamantan-1-yl)acetic acid with (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-nitrile followed by removal of the phthalimide protecting group and treatment with HCl.
References Kovi, Ravishanker, et al.: Apicore, LLC, WO 2012162507 (2012)

Formula: C₆H₈N₂

Color and Shape: Neat

Molecular weight: 108.141

Ref: TR-A795335