Synthesis and odour properties of some saturated and unsaturated ketones and their derivatives

• Autorzy: Gibka, J. , Gliński, M.
• Języki publikacji: EN

Abstrakty

EN

Five ketones, both unsaturated and saturated, which have phenyl and/or t-butyl groups as substituents located at the end of a molecule have been prepared. They were used as starting materials in the synthesis of ethylene and propylene acetals, alcohols and their acetates. Thirteen from twenty three synthesized compounds (all ethylene and propylene acetals, an alcohol and two acetates) have not been described yet. The odour properties for all the prepared compounds have been determined. Most of them have pleasant, fruity-floral odours.

Słowa kluczowe

PL

ketony; acetale; alkohole; estry; synteza; zapach

EN

ketones; acetals; alcohols; esters; synthesis; odour

• Czasopismo: Biotechnology and Food Science
• Rocznik: 2011
• Tom: Vol. 75, nr 1
• Strony: 29-37
• Opis fizyczny: Bibliogr. 18 poz.

Twórcy

autor

Gibka, J.

autor

Gliński, M.

• Institute of General Food Chemistry, Technical University of Lodz, 90-924 Lodz, Poland,

Bibliografia

• 1. Kraft P, Bajgrowicz JA, Denis C, Fráter G. Odds and trends: recent developments in the chemistry of odorants. Angew. Chem. Int. Ed. 2000, 39:2980-3010.
• 2. Fráter G, Bajgrowicz JA, Kraft P. Fragrance Chemistry. Tetrahedron, 1998, 54:7633- 7703.
• 3. Arctander S. Perfume and Flavor Chemicals. S. Arctander, Montclair, 1969.
• 4. Kulesza J, Góra J, Tyczkowski A. Chemia i technologia związków zapachowych. WPLiS, Warszawa, 1961.
• 5. Góra J, Lis A. Olejek drzewa różanego. Aromaterapia, 2000, 6(3):5-9.
• 6. Djerassi C. Dictionary of Natural Products. Chapman & Hall, New York, 1994.
• 7. Góra J, Lis A. Najcenniejsze olejki eteryczne. Wyd. UMK, Toruń, 2005.
• 8. Kołodziejczyk A. Naturalne związki organiczne. WN PWN, Warszawa, 2006.
• 9. Bowers KW, Giese RW, Grimshow J, House HO, Kolodny NA, Kronberger K, Roe DK. Reactions involving electron transfer. I. Reduction of 2,2,6,6-tetramethyl- 4-hepten-3-one. J. Am. Chem. Soc. 1970, 92:2783-2788.
• 10. Hill GA, Bramann GM. Benzopinacolone (1-penten-3-one, 4,4-dimethyl-1- phenyl-), Org. Synth. Coll. 1941, 1:81.
• 11. Wiberg KB, Rowland BI. 1,3-shifts.II. The stereochemistry of the rearrangement of alpha-alkoxystyrenes. J. Am. Chem. Soc. 1955, 77:1159-1163.
• 12. Marcas GB, Municio AM, Vega S. Synthesis of alpha,ß-unsaturated ketones. Reactivity toward SH groups. Anales Real Soc. Espan. Fis. Quim., Ser. B 1964, 60:639-652.
• 13. Berliner E, Berliner F. Hyperconjugation. IV. The bromination of additional monoalkylbenzenes. J. Amer. Chem. Soc. 1950, 72:222-227.
• 14. Ashby EC, Lin J, Goel AB. Reactions of complex metal hydrides of copper with alkyl halides, enones and cyclic ketones. J. Org. Chem. 1978, 43:183-188.
• 15. Armesto D, Horspool WM, Martin JAF, Perez-Ossorio R. Selective reductionof C-C double bonds in conjugated enones by benzylamine. A variant of the sommelet reaction. Tetrahedron Lett. 1985, 26:5217-5220.
• 16. Mulzer J, Bruentrup G, Hartz U, Blaschek U, Boehrer G. Additions of carboxylic acid dianions to alpha, beta-unsaturated carbonyl compounds-control of the 1,2-/1, 4-regioselectivity by steric substituent effects. Chem. Ber. 1981, 114: 3701-3724.
• 17. Whitmore FC, Whitaker JS, Mosher WA, Breivik ON, Wheeler WR, Miner CS, Sutherland LH, Wagner RB, Clapper TW, Lewis CE, Lux AR, Popkin AH. Grignard reductions. IX1,2,3 Further Studies on the reduction of acid halides. Amer. Chem. Soc. 1941, 63:643-654.
• 18. Martinez R, Ramon DJ, Yus M. RuCl2(DMSO)4 catalyzes the ß-alkylation of secondary alcohols with primary alcohols through a hydrogen autotransfer process. Tetrahedron, 2006, 62:8982-8987.