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3-Quinuclidone

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3-Quinuclidone
Names
Other names 1-azabicyclooctan-3-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.989 Edit this at Wikidata
EC Number
  • 223-087-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H11NO/c9-7-5-8-3-1-6(7)2-4-8/h6H,1-5H2Key: ZKMZPXWMMSBLNO-UHFFFAOYSA-N
SMILES
  • C1CN2CCC1C(=O)C2
Properties
Chemical formula C7H11NO
Molar mass 125.171 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H312, H332, H411
Precautionary statements P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

3-Quinuclidinone is a bicyclic organic compounds with chemical formula HC(C2H4)2(C(O)CH2)N. Its basicity is indicated by the pKa of the conjugate acid, which is 7.2. In contrast quinuclidine is about 100x more basic.

Synthesis and reactions

Its hydrochloride salt can be synthesized by a Dieckman condensation: It is a precursor to quinuclidine.

3-quinuclidone hydrochloride synthesis from 1-Carbethoxymethyl-4-carbethoxypiperidine

Organic reduction of 3-quinuclidone gives the compound quinuclidine, structurally related to DABCO, which has one additional bridgehead nitrogen atom.

References

  1. "Quinuclidin-3-one". pubchem.ncbi.nlm.nih.gov.
  2. 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.
  3. H. U. Daeniker, C. A. Grob (1964). "3-Quinuclidone Hydrochloride". Organic Syntheses. 44: 86. doi:10.15227/orgsyn.044.0086.
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