- Structure-activity relationship in the domain of odorants having marine notes
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We synthesized or re-synthesized a large series of 2H-1,5-benzodioxepin- 3(4H)-ones 9 (Scheme 1), 4,5-dihydro-1-benzoxepin-3(2H)-ones 10 (Schemes 3 and 4) and 5,6,8,9-tetrahydro-7H-benzocyclohepten-7-ones 11 (Schemes 5 and 6), since the lead compound for the olfactory note of perfumes based on marine accords is a well-known benzodioxepinone named Calone 1951 (9b). We meticulously described the odor profile of each synthesized compound and discussed relevant structure-odor relationships (Tables 1-3). In particular, we revealed a correlation between the conformation of the seven-membered ring and the activities of these compounds (Table 4 and Fig. 3). We also clarified the effect of the position and the size of the alkyl substituent at the aromatic ring.
- Gaudin, Jean-Marc,Nikolaenko, Olga,De Saint Laumer, Jean-Yves,Winter, Beat,Blanc, Pierre-Alain
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p. 1245 - 1265
(2008/02/07)
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- Conformational analysis of 3-substituted-2,3,4,5-tetrahydro-1-benzoxepin by 1H and 13C nuclear magnetic resonance
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2,3,4,5-Tetrahydro-1-benzoxepin (8) and its 3-substituted derivatives (9-13) have been studied by 1H and 13C dynamic nuclear magnetic resonance in a few solvent systems.The results show that, while 8 and its methyl derivative 9 exist solely in chair forms (C for 8 and Ce:Ca (96:4) for 9), the twist-boat (TB) conformation contributes significantly to the conformational equilibra of the derivatives 3-methoxy 10 (Ca:Ce:TB, 70:20:10), 3,3-dimethyl 11 (C:TB, 90:10), 3,3-methylmethoxy 12 (Ca:Ce:TB, 89:4:7), and 3,3-dimethoxy 13 (C:TB, 92:8).The analysis of several factors (steric, electrostatic, and electronic) on the conformational behaviour of these molecules shows why the TB form is a viable conformational alternative to destabilized chair forms in this benzoxepin system.
- Lachapelle, A.,St-Jacques, M.
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p. 2575 - 2594
(2007/10/02)
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