Production Method 1

2750168-72-8

7677-24-9

856900-26-0

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Diphenyliodonium hexafluorophosphate Catalysts: Cuprous iodide ,  2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile Solvents: Dimethyl sulfoxide ;  2 min; 2 h, rt

Reference

The Merger of Aryl Radical-Mediated Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Cross-Coupling-Type Functionalization of Alkyl Iodides

Caiger, Lewis ; et al, ACS Catalysis, 2023, 13(7), 4985-4991

Production Method 2

143557-91-9

856900-26-0

Reaction Conditions

1.1 Reagents: Imidazole ,  Triphenylphosphine ,  Iodine Solvents: Dichloromethane ;  rt → 0 °C; 0 °C; 16 h, rt
2.1 Reagents: Potassium carbonate ,  Diphenyliodonium hexafluorophosphate Catalysts: Cuprous iodide ,  2,4,5,6-Tetra(9H-carbazol-9-yl)isophthalonitrile Solvents: Dimethyl sulfoxide ;  2 min; 2 h, rt

Reference

The Merger of Aryl Radical-Mediated Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Cross-Coupling-Type Functionalization of Alkyl Iodides

Caiger, Lewis ; et al, ACS Catalysis, 2023, 13(7), 4985-4991

tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate Raw materials

• tert-butyl endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
• tert-butyl exo-3-iodo-8-azabicyclo[3.2.1]octane-8-carboxylate
• trimethylsilanecarbonitrile

tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate Preparation Products

• tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate (856900-26-0)

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tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate (CAS No. 856900-26-0): A Comprehensive Overview

tert-Butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate, identified by the Chemical Abstracts Service Number (CAS No.) 856900-26-0, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal biology. This compound belongs to the class of bicyclic azaboranes, characterized by its intricate molecular structure and potential biological activities. The presence of a cyano group and a tert-butyl moiety contributes to its unique chemical properties, making it a valuable scaffold for drug discovery and development.

The molecular framework of tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate consists of a bicyclic system with an azabicyclo[3.2.1]octane core, which is a rare structural motif in medicinal chemistry. This bicyclic structure imparts rigidity and stability to the molecule, which can be advantageous in terms of binding affinity and metabolic stability. The azabicyclo moiety is particularly noteworthy as it introduces nitrogen into the core structure, which can participate in hydrogen bonding interactions with biological targets, enhancing the compound's potential as a pharmacophore.

The cyano group at the 3-position and the tert-butyl group at the 8-position further modify the electronic and steric properties of the molecule. The cyano group is known for its ability to act as a hydrogen bond acceptor, which can improve interactions with polar residues in protein binding pockets. On the other hand, the tert-butyl group provides steric hindrance, which can help in optimizing binding interactions by preventing unwanted side reactions or promiscuous binding to off-target sites.

Recent advancements in computational chemistry and molecular modeling have enabled researchers to better understand the potential of tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate as a drug candidate. Studies have shown that this compound exhibits promising binding affinity to various biological targets, including enzymes and receptors involved in critical metabolic pathways. For instance, preliminary computational studies suggest that it may interact with enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are implicated in inflammation and pain signaling pathways.

In addition to its potential as an anti-inflammatory agent, tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate has also been investigated for its neuroprotective properties. The azabicyclo core structure is reminiscent of natural products that have been reported to exhibit neuroprotective effects, such as certain alkaloids found in plants. Further research is needed to elucidate the exact mechanisms through which this compound exerts its effects, but initial findings are encouraging.

The synthesis of tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate presents unique challenges due to its complex bicyclic structure. However, recent developments in synthetic methodologies have made it more feasible to produce this compound on a laboratory scale. Techniques such as transition-metal-catalyzed cyclizations and ring-closing metathesis have been employed to construct the azabicyclo core efficiently. These advances have opened up new possibilities for exploring its pharmacological potential.

The pharmacokinetic properties of tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate are also of interest to researchers working in drug development. Initial studies suggest that this compound may exhibit good oral bioavailability and favorable metabolic stability, making it a promising candidate for further clinical investigation. However, more comprehensive pharmacokinetic studies are needed to confirm these findings and optimize dosing regimens.

The role of computational modeling in understanding the biological activity of tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate cannot be overstated. Advanced computational techniques such as molecular dynamics simulations and quantum mechanical calculations have provided insights into how this compound interacts with biological targets at an atomic level. These studies have helped researchers identify key residues involved in binding interactions and predict potential side effects or toxicities.

In conclusion, tert-butyl 3-cyano-8-azabicyclo[3.2.1]octane-8-carboxylate (CAS No. 856900-26-0) is a structurally unique compound with significant potential in pharmaceutical research and development. Its intricate molecular framework, combined with promising biological activities, makes it an attractive scaffold for designing novel therapeutic agents targeting various diseases, including inflammation-related disorders and neurological conditions.

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