3211-87-8

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-bicyclo[2.2.1]heptane-2-carbonitrile is used as a building block for the synthesis of complex molecules and pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs.
Used in Chemical Industry:
(2R)-bicyclo[2.2.1]heptane-2-carbonitrile is used as a potential candidate for drug design and development. Its small and rigid structure allows for its use in creating new compounds with specific properties and functions.

Upstream product

• 2890-96-2 5-norbornene-2-carbonitrile 
• 768-15-0 exo-bicyclo[2.2.1]heptane-2-carboxamide 
• 498-66-8 norbornene 
• 143-33-9 sodium cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 2534-77-2 exo-2-bromonorbornane 
• 585-71-7 (1-bromoethyl)benzne 
• 76649-94-0 endo-bicyclo[2.2.1]heptane-2-carboxamide 
• 934-28-1 bicyclo(2.2.1)heptane-2-endo-carboxylic acid 
• 542-92-7 cyclopenta-1,3-diene 
• 934-29-2 acide bicyclo<2.2.1>heptane carboxylique-2 exo 
• 80605-69-2 endo-2-Norbornylisonitril 
• 2888-90-6 5-norbornene-2-carbonitrile 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 

Downstream Products

• 76649-94-0 endo-bicyclo[2.2.1]heptane-2-carboxamide 

Relevant academic research and scientific papers

Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile

Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules.

Unlocking Mizoroki–Heck-Type Reactions of Aryl Cyanides Using Transfer Hydrocyanation as a Turnover-Enabling Step

A new transfer hydrofunctionalization strategy to turnover H-MII-X complexes has enabled both intra- and intermolecular Mizoroki–Heck (MH)-type reactions of aryl cyanides that are challenging to realize under traditional, basic conditions. Initially, a cascade carbonickelation/MH reaction of 2-cyanostyrenes was achieved using a key alkyne transfer hydrocyanation step. Mechanistic experiments supported the proposed catalytic cycle, including the turnover-enabling transfer hydrocyanation step. The reactivity was then extended to the intermolecular MH reaction of benzonitriles and styrenes.

Azide and Cyanide Displacements via Hypervalent Silicate Intermediates

Hypervalent azido- and cyanosilicate derivatives, prepared in situ by the reaction of trimethylsilyl azide or trimethylsilyl cyanide, respectively, with tetrabutylammonium fluoride, are effective sources of nucleophilic azide or cyanide. Primary and secondary alkyl halides and sulfonates undergo rapid and efficient azide or cyanide displacement in the absence of phase transfer catalysts with the silicate derivatives. Application of these reagents to the stereoselective synthesis of glycosyl azide derivatives is reported.

The synthesis of 2-cyclohexylideneperhydro-4,7-methanoindenes. Non-steroidal analogues of steroidal GABAA receptor modulators

Racemic (3aα,4β,7β,7aα)-2-cyclohexylideneperhydro-4,7- methanoindene derivatives (±)-3 and (±)-4 were synthesised as analogues of steroidal GABAA receptor modulators 1 and 2 respectively. The lithium dianion generated from epimeric 2,3,3a,4,7,7a-hexahydro-4,7-methano-1H-indene-2-carboxylic acids, 8 and 9, reacted with a commercially available cyclohexanone to generate β-hydroxy carboxylic acids. Cyclodehydration to β-lactones followed by the thermal elimination of carbon dioxide gave a suitably functionalised 2-cyclohexylidenehexahydro-4,7-methano-1H-indene derivative 18. Regio- and stereospecific hydrocyanation of the bicyclo[2.2.1]hept-2-ene moiety of 18 was achieved via hydroboration affording a racemic nitrile, 19. This underwent further transformations to give (±)-3 and (±)-4 and their hydroxy group epimers (±)-5 and (±)-6 respectively. X-Ray structure data was obtained for (±)-3. The effects of compounds (±)-3-(±)-6 on the binding of the GABAA receptor agonist [3H]muscimol to rat synaptic membranes were measured. Compound (±)-4 was a weak positive modulator while the others were inactive.

Alkylwanderungen bei Sextettumlagerungen

The migration aptitude of alkyl groups in the Beckmann-, the Criegee-, and the isonitrile-nitrile rearrangements were investigated.The relative rearrangement rates of substituted benzyl groups are an expression of the charge on the migrating carbon at transition state.From the relative rates of migration of exo- and endo-2-norbornyl groups the geometrical changes at the migrating carbon is estimated.Finally, the different influence of α-branching in the migrating group is discussed for these and some other rearrangements.