66113-31-3Relevant articles and documents
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Meinwald,J. et al.
, p. 3485 - 3488 (1971)
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(S)-3,7-Dimethyl-5-octene-1,7-diol and Related Oxygenated Monoterpenoids from Petals of Rosa damascena Mill
Knapp, Holger,Straubinger, Markus,Fornari, Selenia,Oka, Noriaki,Watanabe, Naoharu,Winterhalter, Peter
, p. 1966 - 1970 (2007/10/03)
The methanolic extract obtained from rose flowers was subjected to XAD-2 adsorption chromatography. Prefractionation of the methanolic eluate using multilayer coil countercurrent chromatography (MLCCC) yielded five subfractions. From the least polar subfraction V, a major amount of the key odorants of rose oil, that is, isomeric rose oxides 1a/b, was liberated upon heat treatment at pH 2.5. Further Chromatographic workup of fraction V led, for the first time, to the identification of the genuine rose oxide precursor (S)-3,7-dimethyl-5-octene-1,7-diol (2). In addition to diol 2, the following monoterpene diols have been identified: 3,7-dimethyl-7-octene-1,6-diol (3), 2,6-dimethyl-1,7-octadiene-3,6-diol (4), (2E,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (5), (2E)-3,7-dimethyl-2,7-octadiene-1,6-diol (6), (2Z,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol (7), (2Z)-3,7-dimethyl-2,7-octadiene-1,6-diol (8), (Z)-2,6-dimethyl-2-octene-1,8-diol (9), (E)-2,6-dimethyl-2-octene-1,8-diol (10), (Z)-2,6-dimethyl-2,7-octadiene-1,6-diol (11), (E)-2,6-dimethyl-2,7-octadiene-1,6-diol (12), (2E,6E)-2,6-dimethyl-2,6-octadiene-1,8-diol (13), (2E,6Z)-2,6-dimethyl-2,6-octadiene-1,8-diol (14), 2,6-dimethyloctane-1,8-diol (15), 2,6-dimethyl-7-octene-1,6-diol (16), (E)-3,7-dimethyl-2-octene-1,8-diol (17), (Z)-3,7-dimethyl-2-octene-1,8-diol (18), 3,7-dimethyloctane-1,7-diol (19), 2,6-dimethyl-7-octene-2,6-diol (20), 3,7-dimethyl-6-octene-1,3-diol (21) and (2E)-3,7-dimethyl-2,6-octadiene-1,4-diol (22).
BIS(ARYLSULFONYL)METHANE : A VERSATILE SYNTHON IN PHEROMONE SYNTHESIS
Ferroud, D.,Gaudin, J. M.,Genet, J. P.
, p. 845 - 846 (2007/10/02)
(E)-9-oxo-2-decenoic acid (queen substance) (1); (E)-3,7-dimethyl-2,7-octadienyl propionate (2) and (E)-3,7-dimethyl-2-octene-1,8-diol (3) are easily synthesized via sequential alkylation of bis-(arylsulfonyl)methane 4 with 1,4-allylic substrates 7 and a second electrophile such as 4,4-(ethylenedioxy)pentyl iodide and ethyl 2-methylallyl carbonate.
A New Synthesis of (E)-3,7-Dimethyloct-2-en-1,8-diol, a Component of the Hairpencil Secretion of African Monarch Butterfly
Joshi, N..N.,Mamdapur, V. R.,Chadha, M. S.
, p. 238 - 240 (2007/10/02)
A facile synthesis of the title compound (1) has been achieved.The key intermediate, viz, the keto acid (6) is prepared via a novel route starting from the alkenol (2).Bromination of (2), and subsequent elaboration through the alkylation of diethyl malonate or propionic acid, affords the alkenoic acid (5) which upon oxidation with Jones' reagent in presence of Hg(OAc)2, provides 6.Following a well-established sequence of reactions, 6 is then transformed into 1.
