3-Quinuclidone

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.[2]

3-Quinuclidone
Names
Other names
1-azabicyclo[2.2.2]octan-3-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.989
EC Number
  • 223-087-9
UNII
  • InChI=1S/C7H11NO/c9-7-5-8-3-1-6(7)2-4-8/h6H,1-5H2
    Key: ZKMZPXWMMSBLNO-UHFFFAOYSA-N
  • C1CN2CCC1C(=O)C2
Properties
C7H11NO
Molar mass 125.171 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H312, H332, H411
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 [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

Its hydrochloride salt can be synthesized by a Dieckman condensation:[3] 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.