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a) H. R. Schenk, H. Gutmann, O. Jeger, L. Ruzicka, Helv. Chim. Acta 1954, 37, 543-546;
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P. Kraft, J. A. Bajgrowicz, C. Denis, G. Fráter, Angew. Chem. 2000, 112, 3106-3138;
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Angew. Chem. Int. Ed. 2000, 39, 2980-3010.
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Chem. Int. Ed
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Angew1
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5
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0032890696
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Most powerful isomer: M. Y. Gorbachov, K. J. Rossiter, Chem. Senses 1999, 24, 171-178;
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a) Most powerful isomer: M. Y. Gorbachov, K. J. Rossiter, Chem. Senses 1999, 24, 171-178;
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6
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34548128666
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Corresponding patent application: C. P. Newman, K. J. Rossiter, C. S. Sell (Unilever PLC, United Kingdom), Eur. Pat. Appl. EP 276998A2, 3 August, 1988 (prior. 29 January, 1987) [Chem. Abstr. 1989, 110, 13 401w; AN 1989:13 401].
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b) Corresponding patent application: C. P. Newman, K. J. Rossiter, C. S. Sell (Unilever PLC, United Kingdom), Eur. Pat. Appl. EP 276998A2, 3 August, 1988 (prior. 29 January, 1987) [Chem. Abstr. 1989, 110, 13 401w; AN 1989:13 401].
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7
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34548133941
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Registered names, trademarks, etc. that are used in this article, even when not specifically marked as such, are to be considered to be protected by law
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Registered names, trademarks, etc. that are used in this article, even when not specifically marked as such, are to be considered to be protected by law.
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8
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34548125637
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Most powerful isomer: J. Panten, H.-J. Bertram, H. Surburg in Perspectives in Flavor and Fragrance Research (Eds.: P. Kraft, K. A. D. Swift), Wiley-VCH, Weinheim, 2005, pp. 105-117;
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a) Most powerful isomer: J. Panten, H.-J. Bertram, H. Surburg in Perspectives in Flavor and Fragrance Research (Eds.: P. Kraft, K. A. D. Swift), Wiley-VCH, Weinheim, 2005, pp. 105-117;
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9
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34548142071
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Corresponding patent application: W. Pickenhagen, D. Schatkowski (Dragoco Gerbering & Co AG, Germany), Eur. Pat. Appl. EP 857723A1, 12 August, 1998 (prior. 6 February, 1997) [Chem. Abstr. 1998, 129, 175811z; AN 1998:561304].
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b) Corresponding patent application: W. Pickenhagen, D. Schatkowski (Dragoco Gerbering & Co AG, Germany), Eur. Pat. Appl. EP 857723A1, 12 August, 1998 (prior. 6 February, 1997) [Chem. Abstr. 1998, 129, 175811z; AN 1998:561304].
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10
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0035859716
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Most powerful isomer: J. A. Bajgrowicz, I. Frank, Tetrahedron: Asymmetry 2001, 12, 2049-2057;
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a) Most powerful isomer: J. A. Bajgrowicz, I. Frank, Tetrahedron: Asymmetry 2001, 12, 2049-2057;
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11
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34548128663
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Corresponding patent application: J. A. Bajgrowicz (Givaudan-Roure (International S. A., Switzerland), Eur. Pat. Appl. EP 761664A1, 12 March, 1997 (prior. 11 September, 1995) [Chem. Abstr. 1997, 126, 225430k; AN 1997:238393].
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b) Corresponding patent application: J. A. Bajgrowicz (Givaudan-Roure (International S. A., Switzerland), Eur. Pat. Appl. EP 761664A1, 12 March, 1997 (prior. 11 September, 1995) [Chem. Abstr. 1997, 126, 225430k; AN 1997:238393].
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12
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34548133940
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A.-P. Bonenfant, J. Baudin, H. U. Gonzenbach (Givaudan & Cie (International) S.A., Switzerland), Eur. Pat. Appl. EP 0379981A1, 1 August, 1990 (prior. 27 January 1989) [Chem. Abstr. 1991, 114, 121772j; AN 1991:121772];
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a) A.-P. Bonenfant, J. Baudin, H. U. Gonzenbach (Givaudan & Cie (International) S.A., Switzerland), Eur. Pat. Appl. EP 0379981A1, 1 August, 1990 (prior. 27 January 1989) [Chem. Abstr. 1991, 114, 121772j; AN 1991:121772];
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13
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0010427658
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b) J. Baudin, A. P. Bonenfant, H. U. Gonzenbach, Chimia 1992, 46, 98-100.
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Chimia
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Baudin, J.1
Bonenfant, A.P.2
Gonzenbach, H.U.3
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14
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0013404229
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Publications dealing with C/Si bioisosterism (silicon-based odorants): a) R. Tacke, T. Schmid, C. Burschka, M. Penka, H. Surburg, Organometallics 2002, 21, 113-120;
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Publications dealing with C/Si bioisosterism (silicon-based odorants): a) R. Tacke, T. Schmid, C. Burschka, M. Penka, H. Surburg, Organometallics 2002, 21, 113-120;
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15
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b) R. Tacke, T. Schmid, M. Hofmann, T. Tolasch, W. Francke, Organometallics 2003, 22, 370-372;
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(2003)
Organometallics
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, pp. 370-372
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Tacke, R.1
Schmid, T.2
Hofmann, M.3
Tolasch, T.4
Francke, W.5
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16
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0142258783
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c) T. Schmid, J. O. Daiss, R. Ilg, H. Surburg, R. Tacke, Organometallics 2003, 22, 4343-4346;
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Organometallics
, vol.22
, pp. 4343-4346
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Schmid, T.1
Daiss, J.O.2
Ilg, R.3
Surburg, H.4
Tacke, R.5
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17
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33947116910
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d) M. W. Büttner, M. Penka, L. Doszczak, P. Kraft, R. Tacke, Organometallics 2007, 26, 1295-1298;
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(2007)
Organometallics
, vol.26
, pp. 1295-1298
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Büttner, M.W.1
Penka, M.2
Doszczak, L.3
Kraft, P.4
Tacke, R.5
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18
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34547734347
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e) L. Doszczak, P. Kraft, H.-P. Weber, R. Bertermann, A. Triller, H. Hatt, R. Tacke, Angew. Chem. 2007, 119, 3431-3436;
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(2007)
Angew. Chem
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, pp. 3431-3436
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Doszczak, L.1
Kraft, P.2
Weber, H.-P.3
Bertermann, R.4
Triller, A.5
Hatt, H.6
Tacke, R.7
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19
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34250824718
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Angew. Chem. Int. Ed. 2007, 46, 3367-3371;
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(2007)
Chem. Int. Ed
, vol.46
, pp. 3367-3371
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Angew1
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23144441588
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Publications dealing with C/Si bioisosterism (silicon-based drugs): a) J. O. Daiss, C. Burschka, J. S. Mills, J. G. Montana, G. A. Showell, I. Fleming, C. Gaudon, D. Ivanova, H. Gronemeyer, R. Tacke, Organometallics 2005, 24, 3192-3199;
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Publications dealing with C/Si bioisosterism (silicon-based drugs): a) J. O. Daiss, C. Burschka, J. S. Mills, J. G. Montana, G. A. Showell, I. Fleming, C. Gaudon, D. Ivanova, H. Gronemeyer, R. Tacke, Organometallics 2005, 24, 3192-3199;
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22
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b) J. O. Daiss, C. Burschka, J. G. Mills, J. G. Montana, S. A. Showell, J. B. H. Warneck, R. Tacke, Organometallics 2006, 25, 1188-1198;
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(2006)
Organometallics
, vol.25
, pp. 1188-1198
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Daiss, J.O.1
Burschka, C.2
Mills, J.G.3
Montana, J.G.4
Showell, S.A.5
Warneck, J.B.H.6
Tacke, R.7
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23
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c) G. A. Showell, M. J. Barnes, J. O. Daiss, J. S. Mills, J. G. Montana, R. Tacke, J. B. H. Warneck, Bioorg. Med. Chem. Lett. 2006, 16, 2555-2558;
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Bioorg. Med. Chem. Lett
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, pp. 2555-2558
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Showell, G.A.1
Barnes, M.J.2
Daiss, J.O.3
Mills, J.S.4
Montana, J.G.5
Tacke, R.6
Warneck, J.B.H.7
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24
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33751432534
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d) R. Ilg, C. Burschka, D. Schepman, B. Wunsch, R. Tacke, Organometallics 2006, 25, 5396-5408;
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(2006)
Organometallics
, vol.25
, pp. 5396-5408
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Ilg, R.1
Burschka, C.2
Schepman, D.3
Wunsch, B.4
Tacke, R.5
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25
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DOI: 10.1002/cbic. 200700182
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e) M. W. Büttner, C. Burschka, J. O. Daiss, D. Ivanova, N. Rochel, S. Kammerer, C. Peluso-Iltis, A. Bindler, C. Gaudon, P. Germain, D. Moras, H. Gronemeyer, R. Tacke, ChemBioChem, 2007; DOI: 10.1002/cbic. 200700182.
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(2007)
ChemBioChem
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Büttner, M.W.1
Burschka, C.2
Daiss, J.O.3
Ivanova, D.4
Rochel, N.5
Kammerer, S.6
Peluso-Iltis, C.7
Bindler, A.8
Gaudon, C.9
Germain, P.10
Moras, D.11
Gronemeyer, H.12
Tacke, R.13
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26
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34548119014
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In the case of 6b and 6c, the asymmetric unit contains four crystallographically independent molecules, which are characterized by two different types of structures. These structures differ slightly in the conformation of the heterocyclic system of the 5,8-disila-5,6,7,8-tetrahydro-2- naphthyl moiety and in the orientation of the 1,3-dioxolane ring with respect to the bond between the carbon atom C-2 of the 5,8-disila-5,6,7,8-tetrahydro-2- naphthyl group and the carbon atom C-2 of the 1,3-dioxolane ring.
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In the case of 6b and 6c, the asymmetric unit contains four crystallographically independent molecules, which are characterized by two different types of structures. These structures differ slightly in the conformation of the heterocyclic system of the 5,8-disila-5,6,7,8-tetrahydro-2- naphthyl moiety and in the orientation of the 1,3-dioxolane ring with respect to the bond between the carbon atom C-2 of the 5,8-disila-5,6,7,8-tetrahydro-2- naphthyl group and the carbon atom C-2 of the 1,3-dioxolane ring.
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27
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34548139235
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The racemic mixtures 6a/6d and 6b/6c were obtained analogously to the synthesis of 6a and 6b, respectively, by using racemic propane-1,2-diol instead of (2R)-propane-1,2-diol, and the racemic mixtures 5a/5d and 5b/5c were obtained analogously to the synthesis of 5a and 5b, respectively, by using racemic propane-1,2-diol instead of (2R)-propane-1,2-diol.
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The racemic mixtures 6a/6d and 6b/6c were obtained analogously to the synthesis of 6a and 6b, respectively, by using racemic propane-1,2-diol instead of (2R)-propane-1,2-diol, and the racemic mixtures 5a/5d and 5b/5c were obtained analogously to the synthesis of 5a and 5b, respectively, by using racemic propane-1,2-diol instead of (2R)-propane-1,2-diol.
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28
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34548125636
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The relative configuration is noted with the like and unlike descriptor, see: D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696-702;
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The relative configuration is noted with the like and unlike descriptor, see: D. Seebach, V. Prelog, Angew. Chem. 1982, 94, 696-702;
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29
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0020246368
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Angew. Chem. Int. Ed. Engl. 1982, 21, 654-660. To improve the clarity, we used the full prefix rather than the abbreviations l and u.
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Angew. Chem. Int. Ed. Engl. 1982, 21, 654-660. To improve the clarity, we used the full prefix rather than the abbreviations l and u.
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34548125634
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J. A. Bajgrowicz, unpublished results (Givaudan Schweiz AG, Fragrance Research, Dübendorf), 15 January 1996. GC-odor thresholds (2 panellists): 5a: 0.33, 5b: 8.1, 5c: 0.42, and 5d: 5.3 ng per L air.
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J. A. Bajgrowicz, unpublished results (Givaudan Schweiz AG, Fragrance Research, Dübendorf), 15 January 1996. GC-odor thresholds (2 panellists): 5a: 0.33, 5b: 8.1, 5c: 0.42, and 5d: 5.3 ng per L air.
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34548128662
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Eds, P. Kraft, K. A. D. Swift, Wiley-VCH, Weinheim
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P. Kraft in Perspectives in Flavor and Fragrance Research (Eds.: P. Kraft, K. A. D. Swift), Wiley-VCH, Weinheim, 2005, pp. 136-137.
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Kraft, P.1
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0242472979
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CCDC-200244 and CCDC-200245
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C. A. Gray, M. T. Davies-Coleman, M. R. Caira, C. A. Nathanson, G. A. Wisch, J. Chem. Res. 2003, 405-407. CCDC-200244 and CCDC-200245.
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(2003)
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Gray, C.A.1
Davies-Coleman, M.T.2
Caira, M.R.3
Nathanson, C.A.4
Wisch, G.A.5
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33
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34548142070
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08 software package, Montreal, Quebec, Canada H3A 2R7
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Chemical Computing Group Inc, Molecular Operating Environment MOE
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Chemical Computing Group Inc., Molecular Operating Environment MOE 2006.08 software package, Montreal, Quebec, Canada H3A 2R7, 2006. For further information, see http://www.chemcomp.com.
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(2006)
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G. Ohloff, C. Vial, H. R. Wolf, K. Job, E. Jégou, J. Polonsky, E. Lederer, Helv. Chim. Acta 1980, 63, 1932-1946.
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Job, K.4
Jégou, E.5
Polonsky, J.6
Lederer, E.7
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0004150157
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University of Göttingen, Göttingen, Germany
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a) G. M. Sheldrick, SHELXS-97, University of Göttingen, Göttingen, Germany, 1997;
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(1997)
SHELXS-97
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Sheldrick, G.M.1
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0004150157
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University of Göttingen, Göttingen, Germany
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G. M. Sheldrick, SHELXL-97, University of Göttingen, Göttingen, Germany, 1997.
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(1997)
SHELXL-97
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Sheldrick, G.M.1
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