3-Quinuclidone

Names
Other names

1-azabicyclo[2.2.2]octan-3-one

Identifiers

CAS Number

* 3731-38-2 Y

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

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.

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" (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.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:3-Quinuclidone&oldid=3320078"
*[CID]: Compound ID
*[H302]: Harmful if swallowed
*[H312]: Harmful in contact with skin
*[H332]: Harmful if inhaled
*[H411]: Toxic to aquatic life with long lasting effects
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P271]: Use only outdoors or in a well-ventilated area
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P321]: Specific treatment (see … on this label)
*[P330]: Rinse mouth
*[P391]: Collect spillage
*[P501]: Dispose of contents/container to …