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

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|Section2={{Chembox Properties

| C=7|H=11|N =1|O=1

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|Section3={{Chembox Hazards

| GHS_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}}

| 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.

References

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Category:Quinuclidines

Category:Cyclic ketones