92180-65-9Relevant academic research and scientific papers
INSECT PHEROMONES AND THEIR ANALOGUES XXIV. SYNTHESIS OF LONG-CHAIN 1,5-DIMETHYL-BRANCHED PHEROMONES FROM GERANYL ACETATE
Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Tolstikov, G. A.
, p. 697 - 701 (1990)
Schemes for the synthesis of long-chain 1,5-dimethyl-branched pheromones (7,11-dimethyloctadecane, 15,19-dimethyltritriacontane, and 2-acetoxy-3,7-dimethylpentadecane) from the product of allyl oxidation of geranyl acetate (8-acetoxy-2,6-dimethylocta-2E,6E-dien-1-ol) have been developed.
INSECT PHEROMONES AND THEIR ANALOGUES. XVIII. REGIOSPECIFIC SYNTHESIS OF (+/-)-15,19-DIMETHYLTRITRIACONTANE - A COMPONENT OF THE PHEROMONE OF Stomoxys calcitrans
Odinokov, V. N.,Akhmetova, V. R.,Savchenko, R. G.,Tolstikov, G. A.
, p. 500 - 502 (2007/10/02)
(+/-)-15,19-Dimethyltritriacontane (II) - a component of the pheromone of the stable fly - has been obtained by a five-stage synthesis from dimethylcyclooctadiene (I).The coupling of 1,1-dimethoxy-4-methyl-8-oxonon-4Z-ene with n-C13H27CH=PPh3 (THF; -30 deg C, 2 h; 25 deg C, 15 h; Ar) gave 1,1-dimethoxy-4,8-dimethyldocosa-4Z,8Z(E)-diene (III).The hydrolysis of (III) (TsOH.Py, H2O-Ac, boiling, 4 h) gave the corresponding aldehyde (IV).The condensation of (IV) with n-C10H21CH=PPh3 (THF; -60 to -30 deg C, 2 h, 25 deg C, 15 h) led to 15,19-dimethyltritriaconta-11Z(E),15Z,19Z(E)-triene (V), the exhaustive hydrogenation of which (ethanol, H2, 5percent Pd/C, 25 deg C) gave (II).The substance, the yield in percent, and Rf values are given, respectively: (II), 95, 0.92; (III), 29, 0.74; (IV), 80, 0.72; (V) 50, 0.8.The IR and PMR spectra of compounds (II)-(V) and the mass spectra of (II) and (III) are given.
