Properties and Applications of Quinuclidine

Properties and applications of quinuclidine

Quinuclidine is a white to light yellow crystalline powder at room temperature and pressure, which is soluble in most organic solvents and relatively insoluble in water. Quinuclidine belongs to organo-amines, which have certain basicity and ring tension, and can be used as organic ligands in organic synthesis reactions, mostly for complexing organometallic reagents and catalyzing organic chemical reactions.

Quinuclidine Powder is white to yellowish crystalline powder at room temperature and pressure. It is soluble in most organic solvents and has relatively poor solubility in water. Quinuclidine Powder Materials belong to the class of organic amine compounds with certain alkaline and ring tension, and can be used as organic ligands in organic synthesis reactions. Quinuclidine CAS 100-76-5 is mostly used for complexing organomeric reagents and catalyzing organic chemical reactions.

Conformation

The quinine ring contains a five-membered heterocyclic ring and an alkyl group with a lone pair of electrons on the heterocyclic ring. This lone pair of electrons forms a hydrogen bond with the hydrogen atom on the alkyl group, giving the quinine ring molecule a non-planar conformation. Therefore, the steric structure of quinine rings has an important influence on their physicochemical properties. The quinine ring molecule contains a lone pair of electrons that can form hydrogen bonds. This gives the quinuclidine ring molecule some hydrogen-bonding acceptor and donor properties, which can form hydrogen-bonding interactions with other molecules. In addition, the compound molecule contains a lone pair of electrons that can accept protons and generate the corresponding ionic form. Under weakly acidic conditions, the quinine ring can be protonated to form positively charged ions.

Applications

Applications of quinine rings

Figure 1 Application of quinine rings

In a dry reactor, 30 % H2O2 ( 3 m L) was slowly added to an ice-cold solution (5 m L) of quinuclidine ( 500 mg , 4.5 mmol) under an argon atmosphere. The resulting reaction mixture was allowed to stand at room temperature for 18 h. The reaction of quinine ring was monitored using a silica gel TLC plate with ethyl acetate/isopropanol ( 1 : 1 , v/v) as the solvent. At the end of the reaction, MnO2 ( 2 mg ) was added to the reaction mixture under ice-cold conditions to destroy the excess H2O2, and the resulting reaction mixture was stirred in an ice bath for 1 h. The reaction mixture was slowly brought to ambient temperature, and then the disappearance of H2O2 was monitored using potassium iodide starch test paper. MnO2 was removed by filtration with diatomaceous earth, then acetonitrile (50 ml) was added to the filtrate, the solvent was evaporated under reduced pressure, and the resulting residue was dissolved in MeCN ( 50 mL), the solvent was evaporated, and the process was repeated 2 times to remove water. The residue was then dried overnight under reduced pressure, washed with AcOEt decantation, and the final product was purified by alkaline-treated silica gel column chromatography (ethyl acetate/isopropanol ( 1 : 1, v/v) elution) to give the target product molecule quinine ring N-oxide.