6-Acetyl-2,3,4,5-tetrahydropyridine

6-Acetyl-2,3,4,5-tetrahydropyridine
Names
	Preferred IUPAC name 1-(3,4,5,6-Tetrahydropyridin-2-yl)ethan-1-one
	Other names 1-(3,4,5,6-Tetrahydropyridin-2-yl)ethanone; 2-Acetyl-3,4,5,6-tetrahydropyridine
Identifiers
CAS Number	27300-27-2 ; 25343-57-1 tautomer;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	1446593, 1446593
ChEBI	CHEBI:59533 ; CHEBI:59534 tautomer;
ChemSpider	453844 ;
PubChem CID	520194 tautomer;
	InChI InChI=1S/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3 Key: GNZWXNKZMHJXNU-UHFFFAOYSA-N ; InChI=1/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3 Key: GNZWXNKZMHJXNU-UHFFFAOYAY;
	SMILES O=C(C)C1=NCCCC1; O=C(/C1=N/CCCC1)C;
Properties
Chemical formula	C7H11NO
Molar mass	125.171 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

6-Acetyl-2,3,4,5-tetrahydropyridine, is an aroma compound and flavor that gives baked goods such as white bread, popcorn, and tortillas their typical smell, together with its structural homolog 2-acetyl-1-pyrroline.

6-Acetyl-2,3,4,5-tetrahydropyridine and 2-acetyl-1-pyrroline are usually formed by Maillard reactions during heating of food. Both compounds have odor thresholds below 0.06 ng/l.[1] [2]

Structure and properties

6-Acetyl-2,3,4,5-tetrahydropyridine is a substituted tetrahydropyridine and a cyclic imine as well as a ketone. The compound exists in a chemical equilibrium with its tautomer 6-acetyl-1,2,3,4-tetrahydropyridine that differs only by the position of the double bond in the tetrahydropyridine ring:

	$\rightleftharpoons$
6-Acetyl-2,3,4,5-tetrahydropyridine	(1 : 2)	6-Acetyl-1,2,3,4-tetrahydropyridine

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References

T. J. Harrison, G. R. Dake (2005). "An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline". J. Org. Chem. 70 (26): 10872–10874. doi:10.1021/jo051940a. PMID 16356012.
De Kimpe, Norbert; Stevens, Christian (1993). "A convenient synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, the principle bread flavor component". Journal of Organic Chemistry. 58 (10): 2904–2906. doi:10.1021/jo00062a042.

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[1] T. J. Harrison, G. R. Dake (2005). "An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline". J. Org. Chem. 70 (26): 10872–10874. doi:10.1021/jo051940a. PMID 16356012.

[2] De Kimpe, Norbert; Stevens, Christian (1993). "A convenient synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine, the principle bread flavor component". Journal of Organic Chemistry. 58 (10): 2904–2906. doi:10.1021/jo00062a042.