Six‐Membered Silacycle Odorants: Synthesis and Olfactory Characterization of Si Analogues of Artemone, β‐Dynascone, and Herbac
作者： Junhui Liu , Qidong Zhang , Peng Li , Zhan Qu , Shihao Sun
关键词: Silacyclobutane 、 Odor 、 Stereochemistry 、 Carbon 、 Chemistry
摘要: Si-Artemone (4a), Si-β-Dynascone (5a), and Si-Herbac 6a, which are Si analogues of the commercial fragrance ingredients Artemone (1), β-Dynascone (2), Herbac (3), were synthesized expediently by insertion terminal alkynes into silacyclobutane 7a. The sensory characterization results revealed that 4a 6a had quite similar odor qualities compared with those 1 3, whereas 5a a totally different character relative to 2. In terms threshold values, was slightly more substantive than its carbon analogue 1, less potent approximately one-sixth
sci-hub.se 参考文章(61)
Rainer M�nstedt, Ulrich Wannagat, Sila-Riechstoffe und Riechstoffe-Isostere, 10. Mitt. Ein neuer Weg zu Sila-β-Jonon Monatshefte Fur Chemie. ,vol. 116, pp. 693- 700 ,(1985) , 10.1007/BF00809147
U. Wannagat, V. Damrath, U. Harder, Sila-Riechstoffe und Riechstoff-Isostere, 13. Mitt. Grimm sche Hydridisostere im Bereich der Duftstoffklasse des Linalools Monatshefte Fur Chemie. ,vol. 125, pp. 1159- 1169 ,(1994) , 10.1007/BF00813801
Ulrich Wannagat, Volker Damrath, Andreas Schliephake, Ulrich Harder, Sila-Riechstoffe und Riechstoffe-Isostere. 11. Mitt. Vergleich von Carbinolen und Silanolen mit Thiocarbinolen und Silanthiolen Monatshefte Fur Chemie. ,vol. 118, pp. 779- 788 ,(1987) , 10.1007/BF00809228
Reinhold Tacke, Thomas Schmid, Matthias Hofmann, Till Tolasch, Wittko Francke, Sila-linalool as a pheromone analogue: A study on C/Si bioisosterism Organometallics. ,vol. 22, pp. 370- 372 ,(2003) , 10.1021/OM020703K
Ulrich Wannagat, Volker Damrath, Volker Huch, Michael Veith, Ulrich Harder, Sila-Riechstoffe und Riechstoffisostere XII . Geruchsvergleiche homologer Organoelementverbindungen der vierten Hauptgruppe (C, Si, Ge, Sn) Journal of Organometallic Chemistry. ,vol. 443, pp. 153- 165 ,(1993) , 10.1016/0022-328X(93)80293-K
Stephen Gately, Robert West, Novel therapeutics with enhanced biological activity generated by the strategic introduction of silicon isosteres into known drug scaffolds Drug Development Research. ,vol. 68, pp. 156- 163 ,(2007) , 10.1002/DDR.20177
Leszek Doszczak, Philip Kraft, Hans-Peter Weber, Rüdiger Bertermann, Annika Triller, Hanns Hatt, Reinhold Tacke, Prediction of perception: probing the hOR17-4 olfactory receptor model with silicon analogues of bourgeonal and lilial. Angewandte Chemie. ,vol. 46, pp. 3367- 3371 ,(2007) , 10.1002/ANIE.200605002
Yun Liang, Weizhi Geng, Junnian Wei, Kunbing Ouyang, Zhenfeng Xi, Palladium-catalyzed silyl C(sp3)–H bond activation Organic and Biomolecular Chemistry. ,vol. 10, pp. 1537- 1542 ,(2012) , 10.1039/C2OB06941E
Astrid Sunderkötter, Sabine Lorenzen, Reinhold Tacke, Philip Kraft, Novel Silicon‐Based Patchouli Odorants of the Trialkyl(1‐hydroxy‐1‐methylethyl)silane Type: Design, Synthesis, and Olfactory Properties Chemistry: A European Journal. ,vol. 16, pp. 7404- 7421 ,(2010) , 10.1002/CHEM.201000549
Andrew S. Kende, Catherine M. Mineur, Rene J. Lachicotte, Benzosilacyclohexadienones: synthesis and reactivity Tetrahedron Letters. ,vol. 40, pp. 7901- 7906 ,(1999) , 10.1016/S0040-4039(99)01494-X