Quinuclidine

Quinuclidine^[1]

Names
Preferred IUPAC name 1-Azabicyclo[2.2.2]octane[2]
Other names Quinuclidine[2]
Identifiers
CAS Number	100-76-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:38420 Y
ChEMBL	ChEMBL1209648 Y
ChemSpider	7246 Y
ECHA InfoCard	100.002.625
PubChem	7527
UNII	XFX99FC5VI N
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
SMILES N12CCC(CC1)CC2
Properties
Chemical formula	C7H13N
Molar mass	111.19 g·mol−1
Density	0.97 g/cm3
Melting point	157 to 160 °C (315 to 320 °F; 430 to 433 K)
Boiling point	149.5 °C (301.1 °F; 422.6 K) at 760 mmHg
Acidity (pKa)	12.1 (conjugate acid)
Hazards
Flash point	36.5 °C (97.7 °F; 309.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.^[3] 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 to tropane, which has a slightly different carbon frame.

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

References

1. ↑ Quinuclidine Archived October 15, 2007, at the Wayback Machine. at Sigma-Aldrich
2. 1 2 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 169. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The name quinuclidine is retained for general nomenclature only (see Table 2.6). 
3. ↑ 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.