123194-01-4

Usage

Bicyclic amine

Azabicyclo[2.2.2]octane

Explanation

This term describes the structure of the compound, which consists of two interconnected rings and an amine (NH2) group.

Explanation

A carbonitrile group is a functional group consisting of a carbon atom triple-bonded to a nitrogen atom (C≡N). In 1-Azabicyclo[2.2.2]octane-3-carbonitrile, 3-amino-, it is attached to the third carbon atom of the bicyclic structure.

Explanation

The compound is used as a starting material or intermediate in the synthesis of various pharmaceuticals and agrochemicals, which are chemicals used in the medical and agricultural industries, respectively.

Explanation

Due to its unique structure and reactivity, the compound may have potential uses in the fields of organic synthesis (the formation of carbon-containing compounds) and medicinal chemistry (the design and development of pharmaceuticals).
6. Hazardous if not properly managed

Explanation

The compound can pose risks to human health and the environment if not handled with care. Proper safety measures, such as wearing protective gear and following safety protocols, should be taken when working with this chemical.

Explanation

The compound's unique structure and properties make it a valuable asset in various fields, including chemistry and pharmaceuticals, due to its potential for use in a wide range of applications.

Carbonitrile group

CN

Intermediate in synthesis

Pharmaceutical and agrochemicals

Potential applications

Organic synthesis and medicinal chemistry

Versatile compound

Wide range of potential uses

Upstream product

• 6238-30-8 3-hydroxy-1-azabicyclo[2.2.2]octane-3-carbonitrile 

Downstream Products

• 76883-48-2 quinuclidin-3-amine 
• 125889-79-4 3-aminomethyl-1-azabicyclo<2.2.2>octyl-3-amine 
• 917986-73-3 3'-(3-trifluoromethylphenyl)-quinuclidine-3-spiro-5'-hydantoins trifluoroacetate 
• 1401089-91-5 1-(3-cyanoquinuclidin-3-yl)-3-(2-(3-(prop-1-en-2-yl)phenyl)propan-2-yl)urea 
• 313643-39-9 3-amino-1-azabicyclo[2.2.2]octane-3-carboxylic acid 
• 917986-91-5 3'-(2,4-dimethoxyphenyl)-quinuclidine-3-spiro-5'-hydantoin trifluoroacetate 
• 313643-41-3 C₉H₁₅N₃O 

Relevant academic research and scientific papers

NOVEL SPIRO-QUINUCLIDINYL DERIVATIVES FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM DISORDERS

The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

Novel spiro-quinuclidinyl derivatives for the treatment of central nervous system disorders

The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

Novel spiro-quinuclidinyl derivatives for the treatment of central nervous system disorders

The present invention is directed to novel spiro-quinuclidinyl derivatives, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

(-)-Spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2-one], a Conformationally restricted analogue of acetylcholine, is a highly selective full agonist at the α7 nicotinic acetylcholine receptor

Neuronal nicotinic acetylcholine receptors are members of the ligand-gated ion channel receptor superfamily and may play important roles in modulating neurotransmission, cognition, sensory gating, and anxiety. Because of its distribution and abundance in the CNS, the α7 nicotinic receptor is a strong candidate to be involved in some of these functions. In this paper we describe the synthesis and in vitro profile of AR-R17779, (-)-spiro[1-azabicyclo[2.2.2]octane-3,5'oxazolidin-2'-one] (4a), a potent full agonist at the rat α7 nicotinic receptor, which is highly selective for the rat α7 nicotinic receptor over the α4β2 subtype. Preliminary SAR of AR-R17779 presented here indicate that there is little scope for modification of this rigid molecule as even minor changes result in significant loss of the α7 nicotinic receptor affinity.

Synthesis of 2'-arylazabicyclo-3-spiro-4'(5')-imidazolines

A method is described for the synthesis of a series of 2'-aryl-3-azabicyclospiro-4'(5')-imidazolines via the reaction of azabicyclic 1,2-diamines with aryl imidate salts. Competing reactions in the synthesis of the diamines such as the reduction of amino nitriles with LiAlH4 lead to some anomalous products. In the Pinner synthesis, unstable pyridine-type imidates were stabilized as their N-oxide derivatives.

Novel heterocycles derived from 3-acyloxy- and 3-acetamidoquinuclidines

New quinuclidine derivatives with 3-spiro annelated oxathioline, furanone, and pyrrolinone heterocycles have been synthesized from 3-mesyloxy-, 3-acetoxy-, and 3-acetamidoquinuclidine-3-carbonitrile, respectively, by treatment with base. Treatment of 3-acetamidoquinuclidine-3-carbonitrile (3) with potassium hydride resulted in decyanation whereas alkyllithium reagents attacked the cyano group in 3 to produce the corresponding imines. Oxidative cyclization of the N-benzylated derivative of 3 with palladium acetate gave the tetracyclic compound 5-acetyl-1,4-ethano-1,2,3,4,5,6-hexahydrobenzo[c]-1,5-naphthyridine.