3-Quinuclidone
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| ImageFile = Quinuclidone structures (cropped).png
| ImageSize =
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| IUPACName =
| OtherNames = 1-azabicyclo[2.2.2]octan-3-one
|Section1={{Chembox Identifiers
| CASNo = 3731-38-2
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChEMBL = 377716
| ChemSpiderID = 18381
| EC_number = 223-087-9
| PubChem = 19507
| UNII = P4VF4G5PTA
| StdInChI=1S/C7H11NO/c9-7-5-8-3-1-6(7)2-4-8/h6H,1-5H2
| StdInChIKey = ZKMZPXWMMSBLNO-UHFFFAOYSA-N
| SMILES = C1CN2CCC1C(=O)C2
}}
|Section2={{Chembox Properties
| C=7|H=11|N =1|O=1
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|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|312|332|411}}
| PPhrases = {{P-phrases|261|264|270|271|273|280|301+317|302+352|304+340|317|321|330|362+364|391|501}}
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3-Quinuclidinone is a bicyclic organic compounds with chemical formula {{chem2|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.{{cite journal |doi=10.1021/jo026671s |title=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 |year=2003 |last1=Aggarwal |first1=Varinder K. |last2=Emme |first2=Ingo |last3=Fulford |first3=Sarah Y. |journal=The Journal of Organic Chemistry |volume=68 |issue=3 |pages=692–700 |pmid=12558387 }}
Synthesis and reactions
Its hydrochloride salt can be synthesized by a Dieckman condensation:{{cite journal |doi=10.15227/orgsyn.044.0086 |title=3-Quinuclidone Hydrochloride |journal=Organic Syntheses |year=1964 |volume=44 |page=86|author=H. U. Daeniker, C. A. Grob }} It is a precursor to quinuclidine.
File:3-Quinuclidinone hydrochloride.svg
Organic reduction of 3-quinuclidone gives the compound quinuclidine, structurally related to DABCO, which has one additional bridgehead nitrogen atom.