- Syntheses of the enantiomers of Vulcanolide
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The synthesis of the enantiomers of Vulcanolide ((±)-7) is described, the strongest musk odorant among hundreds of structurally related analogues, by resolution of an intermediate. To this end, we devised a new route which involves the temporary introduct
- Fehr, Charles,Chaptal-Gradoz, Nathalie
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p. 533 - 543
(2007/10/03)
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- Synthesis of (-)-Vulcanolide by enantioselective protonation
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Two efficient enantioselective syntheses of the more active (S,S)-enantiomer of the powerful musk odorant Vulcanolide are described. In both syntheses, the key step is an enantioselective protonation of a ketone enolate. A third enantioselective protonati
- Fehr, Charles,Chaptal-Gradoz, Nathalie,Galindo, Jose
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p. 853 - 858
(2007/10/03)
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- Process for the preparation of novel aromatic compounds
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A process for the preparation of novel compounds with a tetraline-type structure, which are useful as perfuming ingredients, is described.
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- Tetralin formate ester aroma chemicals
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The present invention relates to novel formate ester tetralin compounds having fragrant musk-like aroma.
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- Aromatic compounds, a process for preparation thereof and use of same as perfuming ingredients
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Compound of formula STR1 wherein a) indexes m and n are identical and stand each for an integer number equal to zero, symbols R 1 and R 2 are identical and represent each a hydrogen atom, or are different and represent each a hydrogen atom or a methyl radical, symbols R 5 and R 8 stand each for a methyl radical, symbols R 6 and R 7 can be identical or different and designate each a hydrogen atom or a methyl radical and, either symbol R 4 represents a methyl radical and symbol R 3 stands for a hydrogen atom or a methyl radical, or symbols R 3 and R 4 represent each a methylene radical belonging to a ring such as indicated by the dotted line, with the proviso that the following combinations are excluded:1. R 1 =R 2 =R 3 =R 6 =R 7 =H, or2. R 1 =R 2 =R 3 =H and R 6 or R 7 =CH 3, or3. R 2 =CH 3 and R 3 =R 6 =R 7 =H, or4. R 2 =CH 3 and R 3 =H and R 6 or R 7 =CH 3, or5. R 1 =R 3 =CH 3, or6. R 3 =R 4 =CH 2 and R 2 or R 7 =CH 3 ;or whereinb) indexes m and n are different and define each an integer number equal to 0 or 1, symbol R 2 stands for a hydrogen atom or a methyl radical, symbols R 1 and R 3 designate each a hydrogen atom, symbol R 4 represents a methyl radical and, either symbols R 5 and R 6 are identical (n=1) and represent each a methylene radical belonging to a ring such as indicated by the dotted line, R 7 representing a hydrogen atom and R 8 a methyl radical, or symbol R 5 stands for a methyl radical and symbol R 6 for a hydrogen atom, R 7 and R 8 being then identical (m=1) and designating each a methylene radical belonging to a ring such as indicated by the dotted line;or any mixture of two or more structural isomers of formula (I).Compounds (I) develop odor notes of the musky type and can therefore be used as active ingredients in perfuming compositions and perfumed articles of varied nature.A process for the preparation of compounds (I) is described.
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- New Aromatic Musk Odorants: Design and Synthesis
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By appropriate structural modification of known musk odorants, new strong musk odorants have been discovered.Incorporation of supplementary CH3 or CH2 groups into the basic musk skeleton of type G only slightly modifies the global shape of the molecule but leads to densely packed structures of enhanced lipophilicity.For the consturction of these highly substituted 1,2,3,4-tetrahydrohaphthalenes, new annulation sequences (intramolecular mono- and dialkylations; see Schemes 3, 6, and 8) have been developed and, in certain cases, the design of the target molecules was dictated by both structure-activity-realationship and synthetic considerations (e. g. 46 and 47, Scheme 6).This work also presents an original solution to an analytical problem: the distinction between a C2- and a Cs-symmetrical aromatic hydrocarbon (viz. 71 and 72) by conversion into a complex.
- Fehr, Charles,Galindo, Jose,Haubrichs, Rolf,Perret, Roland
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p. 1537 - 1553
(2007/10/02)
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