3,3,7-TRIMETHYL-4-OCTEN-1-OLS 307 (s,b), 2176 (s), 1248 (s), 1172 (m), 1036 (s), 840 (s). Anal. Calcd. for C•oH2oOSi: C, 65.15 H, 10.93. Found: C, 65.03 H, 10.78. 2- (Dimethyl- (4-methyl- 1 (Z)-pe,te,- 1 -y/)si/yl]eth•,ol (17). Diisobutylaluminum hydride (4 cm 3 of 1M solution in hexane) was added under nitrogen to a hexane (10 cm 3) solution of alcohol 16 (0.3 g, 1.63 mmole), and the reaction mixture was stirred for 4 h. Then the reaction mixture was diluted with ethyl ether (50 cm •) and a 10% solution of NaCI (20 cm'•). The product was extracted with ethyl ether and after work-up was purified by column chromatography. In this way, 0.25 g of pure alcohol 17 was ob- tained: b.p. 63øC/2 mm Hg n•) 2ø = 1.4539 1H NMR (8): 0.11 (s, 6H, -Si(CH•)2-), 0.88 (d, J = 6.7 Hz, 2H, -CH(CH•)2), 1.03 (t, J = 8.3 Hz, 2H, -CH2CH2OH) , 1.48 (s, 1H, -OH), 1.63 (m, 1H, -CH(CH3)2) , 1.99 (ddd, J = 7.3, 6.9 and 1.3 Hz, 2H, -CH2CH=CH), 3.72 (t, J = 8.3 Hz, 2H, -CH2OH), 5.46 (d,t, J = 14.2 and 1.3 Hz, 1H, -CH2CH=CH-), 6.33 (dt, J = 14.2 and 7.3 Hz, 1H, -CH•CH=CH-) IR (cm-•): 3344 (s,b), 1604 (m), 1248 (s), 1172 (m), 1036 (s), 836 (s), Anal. Calcd. for C•oH22OSi: C, 64.45 H, 11.90. Found: C, 64.32 H, 11.74. Alcohol 17 was also obtained in 79% yield by the reduction of epoxide 15 with two equivalents of diisobutylaluminum hydride. Synthesis of •cet•tes 4, 9, 13, 18, •nc119. General procedure: A solution of acetyl chloride (0.0025 mole) in ethyl ether (5 cm •) was added to a cooled (0øC) solution of alcohol (0.002 mole) and anhydrous pyridine (0.004 mole) in ethyl ether (30 cm•), and the reaction mixture was stirred for 2 h. Then water (20 cm •) was added and the product was extracted with ethyl ether (2 x 20 cm•). The combined ethereal solution was washed with 10% CuSO 4 solution, 10% NaHCO3 solution, and brine, and dried (MgSO4). The crude acetates were purified by column chromatography. Their physical and spectral data are given below: 4: Yield: 94% b.p. 62øC/2 mm Hg nD 2ø = 1.4356 1H NMR (8): 0.84 (d, J = 6.6 Hz, 6H, -CH(CH3)•), 0.99 (s, 6H, -C(CH3)•), 1.56 (m, 1H, -CH(CH3)•), 1.60 (t, J = 7.6 Hz, 2H, -CH2CH•O-), 1.84 (m, 2H, -CH:CH=CH-), 2.00 (s, 3H, -C(O)CH3), 4.02 (m, 2H, -CH20-), 5.23-5.30 (m, 2H, -CH=CH-) IR (cm-1): 1740 (s), 1384 (s), 1368 (m), 1244 (s), 1032 (s), 976 (s). Anal. Calcd. for C13H2402: C, 73.54 H, 11.39. Found: C, 73.41 H, 11.42. 9: Yield: 95% b.p. 65øC/2 mm Hg nD 2ø = 1.4410 •H NMR (8): 0.88 (d, J = 6.6 Hz, 6H, -CH(CH3)•, 1.11 (s, 6H,-C(CH3):-) , 1.54 (m, 1H, -CH(CH3):) , 1.71 (t,J = 6.7 Hz, 2H, CH2CH20-), 2.01 (s, 3H, -C(O)CH3), 2.02 (m, 2H, -CH2CH=CH-) , 4.09 (t, J -- 6.7 Hz, 2H, -CH•CH20-), 5.21-5.24 (m, 2H, -CH=CH-) IR (cm-1): 1748 (s), 1468 (s), 1384 (s), 1364 (s), 1236 (s), 1032 (s), 712 (m). Anal. Calcd. for C•3H2402: C, 73.54 H, 11.39. Found: C, 73.35 H, 11.45. 13: Yield: 78% b.p. 64øC/2 mm Hg nD 2ø = 1.4420 1H NMR (8): 0.07 (s, 6H, -Si (CH3)•)-) , 1.02 (m, 2H, -CH:CH20), 0.85 (d, J = 6.6 Hz, 6H, -CH(CH3):), 1.40 (m, 1H, -CH(CH3):), 1.98 (m, 2H, -CH•CH=CH-), 2.00 (s, 3H, -C(O)CH3), 4.11 (m, 2H, -CH:CH:O-), 5.56 (dt, J = 18.5 and 1.3 Hz, 1H, -CH2CH=CH-), 6.00 (dt, J = 18.5 and 6.7 Hz, 1H, -CH•CH=CH-) IR (cm-1): 1740 (s), 1616 (w), 1372 (m), 1360 (m), 1244 (s), 1048 (s), 952 (m), 826 (s). Anal. Calcd. for C•2Hi•O•Si: C, 64.23 H, 8.98. Found: C, 64.15 H, 9.05.

308 JOURNAL OF COSMETIC SCIENCE 18: Yield: 60% b.p. 63.5øC/2 mm Hg nD 20 = 1.4432 •H NMR (8): 0.16 (s, 6H, -Si(CH3)2-), 0.95 (d, J -- 6.6 Hz, 6H, -CH(CH3)2) , 1.05 (t, J = 8.4 Hz, 2H, -CH2CH20-), 1.80 (m, 1H, -CH(CH3)2) , 2.01 (s, 3H, -C(O)CH3), 2.08 (d, j = 6.6 Hz, -CH2C=), 4.20 (t, J = 8.4 Hz, -CH2CH20-) IR (cm •): 2176 (s), 1740 (s), 1240 (s), 1040 (s), 824 (s). Anal. Calcd. for C12H2202Si: C, 63.67 H, 9.79. Found: C, 63.75 H, 9.85. 19: Yield 91% b.p. 67øC/2 mm Hg nD 2ø -- 1.4440, •H NMR (8): 0.13 (s, 6H, -Si(CH3)2-) , 0.88 (d, J -- 6.8 Hz, 6H, -CH(CH3)2, 1.04 (t, J = 8.4 Hz, 2H, -CH2CH20-), 1.61 (m, 1H, -CH(CH3)2) , 1.98 (ddd, j = 7.3, 6.9 and 1.3 Hz, 2H, -CH2CH=CH-), 1.99 (s, 3H, -C(O)CH•), 4.14 (t, j = 8.4 Hz, -CH2CH20-), 5.44 (dr, J = 14.2 and 1.3 Hz, 1H, -CH2CH=CH-), 6.33 (dr, J = 14.2 and 7.3 Hz, 1H, -CH2CH=CH-) IR (cm •): 1740 (s), 1608 (m), 1240 (s), 1048 (s), 712 (m). Anal. Calcd. for C•2H2402Si: C, 63.10 H, 10.59. Found: C, 63.01 H, 10.72. ACKNOWLEDGMENTS We thank Prof. J. G6ra for help in the odor evaluation of our compounds. REFERENCES (1) (2) (3) (4) (5) (6) (7) (8) (9) (lO) (11) (12) (13) (14) (15) C. Wawrzeficzyk, Z. Przepi6rka, and A. Zab2a, Insect growth regulators. Part IX. Syntheses of aryl 3,7-dimethyl-4-octen-l-yl ethers, Po/. J. Chem., 55, 819 (1981). R. Obara, T. Olejniczak, and C. Wawrzeficzyk, Odoriferous derivatives of (E)-3,7,7-trimethyl-4-octen- 1-ol and its 7-sila analogue, J. Soc Cosmet. Chem., 46, 321-328 (1995). R. Tacke, M. Strecker, G. Lambrecht, U. Moser, E. Mutschler, Bioisosteric C/Si exchange in para- sympatholytics of the pridinol type sila drugs, Arch. Pharm., 317, 207 (1984). R. Tacke, M. Strecker, G. Lambrecht, U. Moser, and E. Mutschler, (2-Aminoethyl) cycloalkylphenyl- silanole: Bioisosterer CSi--Austausch bei parasympatholytika vom typ des trihexylphenidyls, Lycrim- ins und Procyclidins, Liebigs Ann. Chem., 922-930 (1983). S. McN. Siebruth, S. Y. Lin, J. F. Engel, J. A. Greenblatt, S. E. Burkart, and D. W. Gammon, "Silane Analogues of MTI-800: Biology and Chemistry," in Recent Advances in the Chemistry of lmect Control J. Crombie, Ed. (Royal Society of Chemistry, Cambridge, 1989), pp. 142-150. I. Ujvary, A. Kis-Tamas, L. Varjes, and L. Nowak, Syntheses of silicon-containing juvenile hormone analogues, Acta Chimica Hungarica, 113, 165-175 (1983). T. Olejniczak, S. Lakota, A. Raszka, and C. Wawrzeficzyk, "Synthesis and Biological Activity of Some Sila-Juvenoids," in Insects: Chemical, Physiological and Environmental Aspects, D. Konopifiska, Ed., 1985, pp. 271-275. R. Munstedt and U. Wannagat, Sila-Riechstoffe und Riechstoffe-Isostere, Ein neur Weg zu Sila-[3- Jonon, Monatsh, 116, 693-700 (1985). R. Munstedt and U. Wannagat, ot-Formylopropenylsilane als Modellsubstanzen flit b-cyclocitral, Liebigs Ann. Chem., 944-945 (1985). U. Wannagat, R. Munstedt, and U. Horder, Sila [3-jonon und verwandte Verbindungen, Liebigs Ann. Chem., 950-958 (1985). E. Vedejs and P. L. Fuchs, Inversion of acyclic olefins by the phosphorus betaine method: Scope and limitations, J. Am. Chem. So• , 95, 822-825 (1973). L. Birkofer and T. Ktihn, Einfache Synthesen von symmetrischen his (trimethylsilyl)-ethen, Chem. Ber., 111, 3119-3123 (1978). H.N. Miller, K.W. Greenlee, J. M. Derlet, and C.E. BooM, Mono- and dialkylacetylenes from vicinal dihalides and sodium amide in liquid ammonia, J, Org. Chem., 19, 1882-1888 (1954). P.M. Milller and D. Lamparsky, Perfurmes--Art, Science and Technology (Elsevier Applied Science, London, 1991), pp. 278-286. L. Bateman, J. I. Cunneen, and E. S. Waight, Geranidenes the decomposition of 2,6-dimethylhept- 5-en-2-ol and some derivatives thereof, J. Chem. Soc., 1714-1718 (1952).