Quinuclidine

Quinuclidine^[1]

IUPAC name 1-Azabicyclo[2.2.2]octane
Identifiers
CAS number	100-76-5^Y
PubChem	7527
ChemSpider	7246^Y
ChEBI	CHEBI:38420^Y
ChEMBL	CHEMBL1209648^Y
Jmol-3D images	Image 1
SMILES N12CCC(CC1)CC2
InChI InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2^Y Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N^Y InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 Key: SBYHFKPVCBCYGV-UHFFFAOYAA
Properties
Molecular formula	C₇H₁₃N
Molar mass	111.18 g/mol
Melting point	157–160 °C
Acidity (pK_a)	11.0 (conjugate acid)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Quinuclidine is an organic compound and a bicyclic amine and used as a catalyst and a chemical building block. It is a strong base with pKa of the conjugate acid of 11.0.^[2] This is due to greater availability of the nitrogen lone pair . It can be prepared by reduction of quinuclidone.

The compound is structurally related to DABCO in which the other bridgehead is also nitrogen and tropane with a slightly different carbon frame.

Quinuclidine is found as a structural component of some biomolecules including quinine.

References

^ Quinuclidine at Sigma-Aldrich
^ Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. (1998). "Azatriquinanes: Synthesis, Structure, and Reactivity". J. Org. Chem. 63 (17): 6016–6020. doi:10.1021/jo980788s. PMID 11672206.