3-Quinuclidone

3-Quinuclidone
Names
	Other names 1-azabicyclo[2.2.2]octan-3-one
Identifiers
CAS Number	3731-38-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL377716;
ChemSpider	18381;
EC Number	223-087-9;
PubChem CID	19507;
UNII	P4VF4G5PTA;
	InChI InChI=1S/C7H11NO/c9-7-5-8-3-1-6(7)2-4-8/h6H,1-5H2 Key: ZKMZPXWMMSBLNO-UHFFFAOYSA-N;
	SMILES C1CN2CCC1C(=O)C2;
Properties
Chemical formula	C7H11NO
Molar mass	125.171 g·mol−1
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H312, H332, H411
GHS precautionary statements	P261, P264, P270, P271, P273, P280, P301+317Script error: No such module "Preview warning".Category:GHS errors, P302+352, P304+340, P317Script error: No such module "Preview warning".Category:GHS errors, P321, P330, P362+364Script error: No such module "Preview warning".Category:GHS errors, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

3-Quinuclidinone is a bicyclic organic compounds with chemical formula HC(C
2H
4)
2(C(O)CH
2)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]

Synthesis and reactions

Its hydrochloride salt can be synthesized by a Dieckman condensation:^[3] It is a precursor to quinuclidine.

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

References

↑ "Quinuclidin-3-one" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/19507#section=Safety-and-Hazards.
↑ 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.
↑ H. U. Daeniker, C. A. Grob (1964). "3-Quinuclidone Hydrochloride". Organic Syntheses 44: 86. doi:10.15227/orgsyn.044.0086.

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Original source: https://en.wikipedia.org/wiki/3-Quinuclidone. Read more

[1] "Quinuclidin-3-one" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/19507#section=Safety-and-Hazards.

[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.

[2]

[3]

3-Quinuclidone

Topic: Chemistry

Synthesis and reactions

References