A tricyclic terpene hydrocarbon — Cyclopinene
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The reduction of the tosylate of filipendulol (2,7,7-trimethylbicyclo[3.1.1]hept-2-en-6-ol) with lithium tetrahydroaluminate in ether has given a hydrocarbon (I), C10H16 (bp 66.5°C/50 mm, n D 20 1.4565, d 20 20 0.8599, [α] D 19 -104.5°. NMR: 0.69 ppm (CH3); 0.95 ppm (CH3); 1.17 ppm (CH3); no signals of olefinic protons. IR: 3054 cm−1 (three-membered ring with gem-protons); 1363 and 1387 cm−1 (gem-CH3); absorption bands of multiple bonds absent. Heating (70°C) (I) with a sulfonated cation-exchange resin in hexane gave α-pinene. The hydrogenation of (I) over PtO2 in acetic acid gave pinane. The most probable structure of (I) is 2,7,7-trimethyltricyclo[3.1.1.O2,4]heptane. The substance has been called cyclopinene.
KeywordsHydrocarbon Heptane Tosylate Multiple Bond Olefinic Proton
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