Synthesis and olfactoric activity of side-chain modified β-santalol analogues
作者： Gerhard Buchbauer , Aneta Sunara , Petra Weiss-Greiler , Peter Wolschann
DOI: 10.1016/S0223-5234(01)01271-5
关键词:
摘要: Three osmophoric points have been postulated to be necessary for the sandalwood scent of beta-santalol derivatives. One these points, close hydroxyl group, is highly specific on stereochemistry and, in particular, molecular shape. The role 2-methyl group side chain derivatives was studied by replacement through a hydrogen atom, an ethyl or isopropyl group. It turns out that any change at substituent leads complete loss odour.
elsevier.com
sci-hub.se 参考文章(22)
G. Buchbauer, H. Spreitzer, F. Zechmeister-Machhart, C. Haunschmidt, F. Tr�scher, Synthese und Geruch von (E)- und (Z)-bis-homo-ß-Santalol Monatshefte Fur Chemie. ,vol. 127, pp. 747- 753 ,(1996) , 10.1007/BF00817266
G. Buchbauer, H. Spreitzer, B. �ckher, C. Pretterklieber, I. Piringer, P. Wolschann, Synthese und Geruch von (Z)-Dehydro-homo-β-santalol Monatshefte Fur Chemie. ,vol. 126, pp. 467- 472 ,(1995) , 10.1007/BF00813209
Helmut Spreitzer, Ingrid R��lhuber, Harald Kienzl, Elke D�rrer, Gerhard Buchbauer, Struktur/Geruchs-Beziehungen von mit β-Santalol verwandten Verbindungen: E -Homo-β-santalol und E -Dehydrohomo-β-santalol Monatshefte Fur Chemie. ,vol. 121, pp. 195- 201 ,(1990) , 10.1007/BF00809532
D. Lamparsky, P. M. Müller, Perfumes : art, science, and technology Elsevier Applied Science. ,(1991)
Ernst Theo. Theimer, Fragrance Chemistry: The Science of the Sense of Smell ,(2012)
W.Clark Still, Cesare Gennari, Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination. Tetrahedron Letters. ,vol. 24, pp. 4405- 4408 ,(1983) , 10.1016/S0040-4039(00)85909-2
Gerhard Buchbauer, Helmut Spreitzer, Friederike Zechmeister-Machhart, Alexander Klinsky, Petra Weiβ-Greiler, Peter Wolschann, Synthesis and olfactoric activity of keto-β-santalol and methoxy-β-santalol European Journal of Medicinal Chemistry. ,vol. 33, pp. 463- 470 ,(1998) , 10.1016/S0223-5234(98)80047-0
Stanley H. Pine, Robert J. Pettit, Gregory D. Geib, Susana G. Cruz, Claudio H. Gallego, Tomas Tijerina, Randall D. Pine, Carbonyl methylenation using a titanium-aluminum (Tebbe) complex Journal of Organic Chemistry. ,vol. 50, pp. 1212- 1216 ,(1985) , 10.1021/JO00208A013
Gerhard Buchbauer, Alexander Hillisch, Karin Mraz, Peter Wolschann, Conformational Parameters of the Sandalwood‐Odor Activity: Conformational calculations on sandalwood odor Helvetica Chimica Acta. ,vol. 77, pp. 2286- 2296 ,(1994) , 10.1002/HLCA.19940770816
Wayne I. Fanta, William F. Erman, Synthesis of (+-)-dihydro-.beta.-santalol Journal of Organic Chemistry. ,vol. 37, pp. 1624- 1630 ,(1972) , 10.1021/JO00975A036