{{Chembox | ImageFile = Quinuclidone structures (cropped).png | ImageSize = | ImageAlt = | PIN = 1-Azabicyclo[2.2.2]octan-3-one | OtherNames = |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 | MolarMass = | Appearance = | Density = | MeltingPt = | MeltingPt_notes = | BoilingPt = | BoilingPt_notes = | Solubility = }} |Section3={{Chembox Hazards | GHS_ref=<ref>{{cite web |title=Quinuclidin-3-one |url=https://pubchem.ncbi.nlm.nih.gov/compound/19507#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> | 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}} | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''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.<ref>{{cite journal |doi=10.1021/jo026671s |title=Correlation between p''Ka'' 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 }}</ref>
==Synthesis and reactions== Its hydrochloride salt can be synthesized by a Dieckman condensation:<ref>{{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 }}</ref> It is a precursor to quinuclidine. thumb|center|500px|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== {{reflist}}
{{DEFAULTSORT:Quinuclidone, 3-}} Category:Quinuclidines Category:Cyclic ketones