アピトン樹脂中の新セスキテルペン炭化水素

概要

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A new natural sequiterpenic hydrocarbon C_<15>H_<26>, named tentatively "Apitonene-1", was isolated from the resin of Apitong timber, presumably Dipterocarpus gracilis, imported from the Philippines, by distillation of followed by chromatography on silica gel impregnated with silver nitrate. Dehydrogenation with sulphur gave S-guaiazulene (II) showing hydroguaiazulenic skeleton of the hydrocarbon. The hydrogenation in acetic acid in the presence of Adams catalyst gave a saturated hydrocarbon C_<15>H_<28> whose IR spectrum nearly coincided with that of guaiane (I). In ethanol, however, no hydrogenation occurred. The IR spectrum of the original hydrocarbon (Apitonene-I) showed the presence of isopropyl group (1381, 1364, 1172 cm^<-1>) and excluded the presence of double bond outside the ring system. The mass spectrum of the original and the dihydrocompound showed molecular weight 206 and 208 respectively and the presence of isopropyl and methyl groups. Although the position of unsaturation in the ring system remains undecided, we may estimate the gross structure of "Apitonene-1" either 4,10-dimethyl-7-isopropyl-bicyclo [0,3,5]-deca-4-ene(IV) or 4,10-dimethyl-7-isopropyl-bicyclo [0,3,5]-deca-10-ene (V) from the results of its NMR spectrum.
社団法人日本材料学会の論文
1967-10-15