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Structure‐odour correlation, part XV 1 : Macrocyclic spiro ethers
Author(s) -
Weyerstahl Peter,
Brendel Joachim,
Glasow Lutz
Publication year - 1992
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.2730070102
Subject(s) - chemistry , camphor , steric effects , ring (chemistry) , stereochemistry , organic chemistry , medicinal chemistry
From cyclooctanone (1) and cyclododecanone (2) the spiro ethers 18–23 were prepared via the yne‐diols 6–11 and the ene‐diols 12–17. Hydrogenation of 21–23 leads to the spiro tetrahydrofurans 24–26. Olfactive evaluation showed that the odour of 18 (camphor, fresh, green) is very similar to that of the unsubstituted analogue B (R 1 , R 2 = H). This can be explained by a similar steric situation of the osmophoric dihydrofuran ring in both these compounds. Increasing substitution at C‐2 (18 → 19 → 20) diminishes the camphoraceous sensation stepwise with increasing herbaceous notes. The macrocyclic spiro ethers 21–23 exhibit interesting woody fragrances with different undertones. Particularly, 22 is most pleasant with some powdery, balsamic and musk notes. The saturated spiro ethers 24–26 smell similar but very weak.