Odor-structure relationships using fluorine as a probe
Michel, Dominique; Schlosser, Manfred
2000

Résumé

Eight ethers, nine esters and one ketone were submitted to a systematic structural variation by replacing a hydrogen atom in the vicinity of the oxo function by fluorine and Me. As long as steric factors dominate, a fluorine substituent alters the olfactory properties of the parent compd. much less than a Me substituent does. However, if it occupies a position adjacent to a carbonyl group, the halogen may more profoundly affect the odor perception, presumably as a consequence of conformational changes. [on SciFinder (R)]

Détails

Titre Odor-structure relationships using fluorine as a probe
Auteur(s) Michel, Dominique ; Schlosser, Manfred
Publié dans Tetrahedron
Volume 56
Numéro 25
Pages 4253-4260
Date 2000
ISSN 0040-4020
Mots-clés (libres)
Note CAN 133:163900
24-6
Alicyclic Compounds
Section de Chimie (BCh),Universite of Lausanne,Lausanne,Switz.
Journal
written in English.
103-48-0P (2-Phenylethyl isobutyrate); 140-26-1P (2-Phenylethyl isovalerate); 142-19-8P (Heptanoic acid 2-propenyl ester); 502-72-7P (Cyclopentadecanone); 2986-50-7P ((2-Methylpropoxy)cyclododecane); 2986-53-0P (Ethoxycyclododecane); 2986-54-1P (Methoxycyclododecane); 2986-72-3P ((Allyloxy)cyclododecane); 3098-11-1P; 6221-92-7P (Cyclododecanol acetate); 6221-94-9P (Cyclododecanol propanoate); 52914-66-6P (2-Methylcyclopentadecanone); 67662-96-8P (2-Phenylethyl pivalate); 67845-47-0P (Propoxycyclododecane); 104023-26-9P (2-Methylpropanoic acid cyclododecyl ester); 140141-24-8P (Heptanoic acid 2-methyl-2-propenyl ester); 287965-62-2P ([(2-Fluoro-2-propenyl)oxy]cyclododecane); 287965-63-3P ((2-Fluoropropoxy)cyclododecane); 287965-67-7P (cis-1-Fluoro-2-methoxycyclododecane); 287965-68-8P (trans-1-Fluoro-2-methoxycyclododecane); 287965-69-9P (cis-1-Methoxy-2-methylcyclododecane); 287965-70-2P (trans-1-Methoxy-2-methylcyclododecane); 287965-71-3P (cis-1-Ethoxy-2-fluorocyclododecane); 287965-72-4P (trans-1-Ethoxy-2-fluorocyclododecane); 287965-73-5P (cis-1-Ethoxy-2-methylcyclododecane); 287965-74-6P (trans-1-Ethoxy-2-methylcyclododecane); 287965-75-7P (cis-1-(Allyloxy)-2-fluorocyclododecane); 287965-76-8P (trans-1-(Allyloxy)-2-fluorocyclododecane); 287965-77-9P (cis-1-(Allyloxy)-2-methylcyclododecane); 287965-78-0P (trans-1-(Allyloxy)-2-methylcyclododecane); 287965-79-1P (cis-2-Fluorocyclododecanol acetate); 287965-80-4P (trans-2-Fluorocyclododecanol acetate); 287965-81-5P (cis-2-Methylcyclododecanol acetate); 287965-82-6P (trans-2-Methylcyclododecanol acetate); 287965-83-7P (cis-2-Fluorocyclododecanol propanoate); 287965-84-8P (trans-2-Fluorocyclododecanol propanoate); 287965-85-9P (cis-2-Methylcyclododecanol propanoate); 287965-86-0P (trans-2-Methylcyclododecanol propanoate); 287965-87-1P (cis-2-Fluorocyclododecyl isobutyrate); 287965-88-2P (trans-2-Fluorocyclododecyl isobutyrate); 287965-89-3P (cis-2-Methylcyclododecyl isobutyrate); 287965-90-6P (trans-2-Methylcyclododecyl isobutyrate); 287965-91-7P; 287965-92-8P; 287965-94-0P (3-Fluoro-3-methyl-butanoic acid 2-phenylethyl ester); 287965-95-1P; 287965-96-2P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. of fluorinated ethers, esters, ketones and their odor-structure relationship); 60-12-8 (2-Phenylethanol); 74-88-4 (Methyl iodide); 75-16-1 (Methylmagnesium bromide); 75-36-5 (Acetyl chloride); 79-03-8 (Propionyl chloride); 79-30-1 (Isobutyroyl chloride); 106-95-6 (Allyl bromide); 107-08-4 (Propyl iodide); 107-18-6 (2-Propen-1-ol); 108-12-3 (Isovaleroyl chloride); 286-99-7 (1,2-Epoxycyclododecane); 513-38-2 (Isobutyl iodide); 513-42-8 (2-Methyl-2-propen-1-ol); 563-47-3 (2-Methyl-2-propenyl chloride); 1070-83-3 (3,3-Dimethylbutyric acid); 1502-29-0 (cis-1,2-Epoxycyclododecane); 1724-39-6 (Cyclododecanol); 2528-61-2 (Heptanoyl chloride); 3282-30-2 (Pivaloyl chloride); 3785-33-9 (Bromoacetic acid 2-phenylethyl ester); 5675-31-0; 7065-46-5 (3,3-Dimethylbutyroyl chloride); 73602-61-6 (Triethylamine trihydrofluoride); 131600-43-6 (N-Ethyl-N-(1-methylethyl)-2-propanamine trihydrofluoride); 140616-89-3 (2-Fluoro-2-methylpropanoyl chloride) Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of fluorinated ethers, esters, ketones and their odor-structure relationship); 4683-60-7P (trans-1,2-Epoxycyclododecane); 36229-60-4P (trans-2-Methylcyclododecanol); 36229-61-5P (cis-2-Methylcyclododecanol); 287965-65-5P (trans-2-Fluorocyclododecanol); 287965-66-6P ((3-Bromo-2-fluoropropoxy)cyclododecane); 287965-93-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of fluorinated ethers, esters, ketones and their odor-structure relationship); 287965-64-4P (cis-2-Fluorocyclododecanol) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of fluorinated ethers, esters, ketones and their odor-structure relationship)
DOI https://doi.org/10.1016/S0040-4020(00)00351-3
Laboratoires LSCO
Le document apparaît dans Production scientifique et compétences > SB - Faculté des sciences de base > SB Archives > LSCO - Laboratoire de synthèse organique et catalyse
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Date de création de la notice 2006-03-03