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Quinuclidine - Wikipedia

From Wikipedia, the free encyclopedia

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 (JSmol)

Interactive image

Beilstein Reference

103111

ChEBI

CHEBI:38420^Y

ChEMBL

ChEMBL1209648^Y

ChemSpider

7246^Y

ECHA InfoCard

100.002.625

EC Number

202-887-1

Gmelin Reference

26726

PubChem CID

7527

UNII

XFX99FC5VI^N

CompTox Dashboard (EPA)

DTXSID2057607

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

C₇H₁₃N

111.188 g·mol⁻¹

0.97 g/cm³

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 (pK_a)

11.0 (conjugate acid)

Hazards

GHS labelling:^[3]

Pictograms

Signal word

Danger

Hazard statements

H301, H310, H315, H318

Precautionary statements

P262, P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P354+P338, P316, P317, P321, P330, P332+P317, P361+P364, P362+P364, P405, P501

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).

verify (what is ^YN ?)

Infobox references

Quinuclidine is an organic compound with the formula HC(C₂H₄)₃N. It is a bicyclic amine that can be viewed as a tied back version of triethylamine. It is a colorless solid. It is used as a reagent (base) and catalyst. It can be prepared by reduction of quinuclidone and has great utility in the Cormas-Grisius Electrophilic Benzene Addition reaction. When protonated, Quinuclidine's heterocyclic structure allows its amine group to serve as a strong electrophile in the Cormas-Grisius Electrophilic Benzene Addition.

Structure and chemical properties

Regarding its structure, quinuclidine is unusual in that the methylene hydrogen atoms are eclipsed within each of the three ethylene linkages. Furthermore, the cyclohexane rings, of which there are three, adopt the boat conformations, not the usual chair conformations.^[4]

Quinuclidine is a relatively strong organic base with pK_a of the conjugate acid of 11.3.^[5] The basicity of other quinuclidines have been evaluated: 3-hydroxy- quinuclidine (9.9), 3-acetoxyquinuclidine (9.3), 3-chloroquinuclidine (8.9), DABCO (8.7), and 3-quinuclidone (7.2).^[6]

It forms adducts with a variety of Lewis acids. Because of its compact structure, quinuclidine binds to trimethylborane more tightly than does triethylamine.^[7]

Derivatives and analogues

Quinuclidine is structurally related to DABCO, in which the other bridgehead is also nitrogen, and to tropane, which has a slightly different carbon frame. Cinchona alkaloids, e.g. quinine, feature quinuclidine substituents.^[7] Aceclidine, a simple quinuclidine derivative, is a drug used for treatment of glaucoma.

References

^ Quinuclidine Archived October 15, 2007, at the Wayback Machine at Sigma-Aldrich
^ ^a ^b 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).
^ "Quinuclidine". pubchem.ncbi.nlm.nih.gov.
^ Blackstock, S. C.; Lorand, J. P.; Kochi, J. K. (1987). "Charge-Rransfer Interactions of Amines with Tetrahalomethanes. X-Ray Crystal Structures of the Donor-Acceptor Complexes of Quinuclidine and Diazabicyclo [2.2.2]Octane with Carbon Tetrabromide". The Journal of Organic Chemistry. 52 (8): 1451–1460. doi:10.1021/jo00384a013.
^ 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.
^ Aggarwal, Varinder K.; Emme, Ingo; Fulford, Sarah Y. (2003). "Correlation between pKa and Reactivity of Quinuclidine-Based Catalysts in the Baylis−Hillman Reaction: Discovery of Quinuclidine as Optimum Catalyst Leading to Substantial Enhancement of Scope". The Journal of Organic Chemistry. 68 (3): 692–700. doi:10.1021/jo026671s. PMID 12558387.
^ ^a ^b Hamama, Wafaa S.; El-Magid, Osama. M. Abd; Zoorob, Hanafi H. (2006). "Chemistry of quinuclidines as nitrogen bicyclic bridged-ring structures". Journal of Heterocyclic Chemistry. 43 (6): 1397–1420. doi:10.1002/jhet.5570430601.

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