Quinuclidine

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Quinuclidine[1]
Skeletal formula of quinuclidine
Skeletal formula of quinuclidine
Ball-and-stick model of quinuclidine
Ball-and-stick model of quinuclidine
Names
Preferred IUPAC name
1-Azabicyclo[2.2.2]octane[2]
Other names
Quinuclidine[2]
Identifiers
3D model (
JSmol
)
103111
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.002.625 Edit this at Wikidata
EC Number
  • 202-887-1
26726
UNII
  • InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 checkY
    Key: SBYHFKPVCBCYGV-UHFFFAOYSA-N checkY
  • InChI=1/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2
    Key: SBYHFKPVCBCYGV-UHFFFAOYAA
  • N12CCC(CC1)CC2
Properties
C7H13N
Molar mass 111.188 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) 11.0 (conjugate acid)
Hazards
GHS labelling:[3]
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H301, H310, H315, H318
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).
☒N verify (what is checkY☒N ?)

Quinuclidine is an

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
.

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

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

Quinine is a quinuclidine derivative.

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

  1. ^ Quinuclidine Archived October 15, 2007, at the Wayback Machine at Sigma-Aldrich
  2. ^
    ISBN 978-0-85404-182-4
    . The name quinuclidine is retained for general nomenclature only (see Table 2.6).
  3. ^ "Quinuclidine". pubchem.ncbi.nlm.nih.gov.
  4. doi:10.1021/jo00384a013
    .
  5. PMID 11672206
    .
  6. PMID 12558387
    .
  7. ^
    doi:10.1002/jhet.5570430601
    .
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