1489-47-0Relevant academic research and scientific papers
INSECT PHEROMONES AND THEIR ANALOGUES XLIII. CHIRAL PHEROMONES FROM (S)-(+)-3,7-DIMETHYLOCTA-1,6-DIENE 3. SYNTHESIS OF (4R)-4-METHYLNONAN-1-OL - SEX PHEROMONE OF Tenebrio molitor AND ITS RACEMIC ANALOGUE
Odinokov, V. N.,Ishmuratov, G. Yu.,Yakovleva, M. P.,Sokol'skaya, O. V.,Kharisov, R. Ya.,et al.
, p. 618 - 621 (1992)
Starting from the readily available enantiomerically enriched (S)-(+)-3,7-dimethylocta-1,6-diene (ee ca. 50percent), we have synthesized (4R)-4-methylnonan-1-ol - the sex pheromone of the yellow mealworm bettle Tenebrio molitor L.A scheme for synthesizing the racemic analogue of the pheromone from 4-methyltetrahydropyran has been developed.
Studies related to fatty acid desaturation. Part I: Preparation of methyl-substituted nonanols, nonyl bromides and total synthesis of new branched oleic acids
Genard, S.,Patin, H.
, p. 397 - 406 (2007/10/02)
Convenient pathways for the synthesis of seven structurally defined isomers of methyl-nonanols and methyl-nonylbromides are described.These synthons are used to perform Wittig reactions between convenient phosphoranes and aldehydes in order to obtain seven new octadecenoic acids bearing a methyl grouping on carbons 11 to 17. branched nonan-1-ols / branched 1-nonylbromides / Wittig reactions / methyl 9-bromononanoate / methyl 8-formyloctanoate / methyl 11 or 17-methyloctadec-9-enoates
THE RACEMIC FORM AND THE TWO ENANTIOMERS OF 4-METHYL-1-NONANOL, A SEX ATTRACTANT OF THE YELLOW MEALWORM, Tenebrio molitor L.
Carpita, Adriano,Magistris, Elisabetta De,Rossi, Renzo
, p. 99 - 106 (2007/10/02)
The racemic form of 4-methyl-1-nonanol, (R)(S)-1, a sex attractant secreted by the female of the yellow mealworm, has been synthesized in 31 percent overall yield from commercially available methyl 2-octynoate, 2.Almost enantiomerically pure (R)- and (S)-1 have been stereospecifically synthesized in 21.3 and 23.9 percent overall yields, respectively, starting from methyl hydrogen (R)-3-methylglutarate, (R)-3.A precursor for (S)-1, i.e. (S)-3-methyloctanoic acid, (S)-4, has been also prepared in 84 percent yield and over 96 percent enantiomeric purity by the BF3-mediated 1,4-addition of n-pentylcopper to (-)-8-phenylmenthyl crotonate, 15, followed by saponification.The enantiomeric purities of methyl (R)-3-methyloctanoate, (R)-7, and (S)-3-methyl-1-octanol, (S)-8, have been determined by converting these compounds into (R)- and (S)-3-methyloctanoic acid, (R)-4 and (S)-4, respectively, followed by GLC analysis of the corresponding 1-(1-naphthyl)ethylamides obtained from nearly optically pure (R)-1-(1-naphthyl)ethylamine.
