27 Allium属植物に存在する環状硫黄化合物の構造

概要

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From the steam volatile oils of the title plant, four novel cyclic sulfur compound were isolated to be respectively determined as 3,5-dialkyl trithiolan (3-6). The steam volatile oil was subjected to column chromatography on alumina, and cyclic sulfur compounds separated from the benzene fraction. Compound of (1), M^+180, analysed for C_6H_<12>S_3. The physical data (including i.r. n.m.r. and m.s.) suggest that is a dialkyl trithiolan with structure (1) or (2). The low-field position of the methine protone (δ ca 4.6) suggests structure (1) in which the hydrogen is adjacent to two sulfur atoms rather than (2). No optical activity was detected for compound of (3) and (4), indicating cis-isomer and trans-form. From difference of shift of each proton on the n.m.r., and an intense i.r. band at 720Cm^<-1> is evidence for the cis-form, determined (4) is cis-3,5-diethyl 1,2,4-trithiolan, (3) is trans-3,5-diethyl 1,2,4-trithiolan. Similarly, compound (5) and (6), M^+166, analysed for C_5H_<10>S_3. From physical data determined (5) is trans-3-methyl 5-ethyl 1,2,4-trithiolan, (6) is cis-3-methyl 5-ethyl 1,2,4-trithiolan.
天然有機化合物討論会の論文
1978-08-22