765-17-3Relevant academic research and scientific papers
Bidirectional, organocatalytic synthesis of lepidopteran sex pheromones
De Figueiredo, Renata Marcia,Berner, Raphael,Julis, Jennifer,Liu, Ting,Tuerp, David,Christmann, Mathias
, p. 640 - 642 (2007/10/03)
Shuffling of two simple building blocks and a regioselective transfer hydrogenation allow for the rapid synthesis of a small collection of lepidopteran sex pheromones, e.g., 8E,10Z-tetradeca-8,10-dienal 5c, from the horse chestnut leafminer (Cameraria ohridella).
Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, lepidoptera pheromone components, via zinc reduction of enyne precursors. Test of pheromone efficacy against the Siberian moth
Khrimian, Ashot,Klun, Jerome A.,Hijji, Yousef,Baranchikov, Yuri N.,Pet'Ko, Vladimir M.,Mastro, Victor C.,Kramer, Matthew H.
, p. 6366 - 6370 (2007/10/03)
Efficient syntheses of (Z,E)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semihydrogenation was ≥98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80 °C were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.
A facile preparation of geometrically pure alkenyl, alkynyl, and aryl conjugated Z-alkenes: Stereospecific synthesis of bombykol
Uenishi, Jun'Ichi,Kawahama, Reiko,Izaki, Yoshiyuki,Yonemitsu, Osamu
, p. 3493 - 3500 (2007/10/03)
Ni- and Pd-catalyzed cross coupling reactions of 2-alkenyl, 2-alkynyl, and 2-aryl substituted (1Z)-1-bromoalkene with alkyl Grignard reagents gave 1-alkyl substituted (1Z,3E)-diene, (1Z)-en-3-yne, and (1Z)-2-arylethene, each in good yield. When (trimethylsilyl)-methylmagnesium chloride was used as the Grignard reagent, conjugated Z-allylsilane was produced. Bombykol, (10E, 12Z)-10,12-hexadecadien-1-ol, a sex pheromone of female moss, Bombyx mori, was synthesized stereospecifically. 2000 Elsevier Science Ltd.
Alkene ozonolysis and the study of reactions of polyfunctional compounds: LXI. New synthetic route to bombycol, pheromone of mulberry silkworm
Kukovinets,Kasradze,Chernukha,Odinokov,Dolidze,Galin,Spirikhin,Abdullin,Tolstikov
, p. 1156 - 1159 (2007/10/03)
Starting from a product of partial ozonolysis of 1,4-cyclohexadiene, methyl (E)-6-oxo-4-hexenoate, a new synthetic route was developed for (10E, 12Z)-hexadeca-10,12-dien-1-ol (bombycol), the main component of sex pheromone of mulberry silkworm (Bombix mori).
Stereospecific synthesis of (E,Z)- and (Z,Z)-hexadeca-10,12-dienal. Sex pheromone components of Diaphania hyalinata
Cabezas, Jorge A.,Oehlschlager, Allan C.
, p. 107 - 111 (2007/10/03)
Isomeric (E,Z)- and (Z,Z)-hexadeca-10,12-dienal were prepared, stereospecifically, in 51% and 43% overall yields from dec-1-yne.
Sex pheromone of the common sheep moth, Hemileuca eglanterina, from the San Gabriel Mountains of California
McElfresh, J. Steven,Millar, Jocelyn G.
, p. 687 - 709 (2007/10/03)
The sex pheromone of Hemileuca eglanterina from the San Gabriel Mountains, California, was determined to be a combination of E10,Z12- hexadeca-10,12-dien-1-yl acetate, E10,Z12-hexadeca-10,12-dien-1-ol, and E10,Z12-hexadeca-10,12-dienal. Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100:48:1.1 of the acetate, alcohol, and aldehyde, respectively. Field trials with synthetic compounds indicated that the optimum ratio of alcohol to aldehyde was 10:1 and that this ratio was more critical than the ratio of either compound to the acetate. A synthetic blend of 100:10:1 acetate-alcohol-aldehyde was effective at attracting male moths in the field. Additional compounds found in both extract and aeration samples failed to significantly increase trap catches of male moths, although some of these minor components elicited responses from male moth antennae in coupled gas chromatography-electroantennography studies.
INSECT PHEROMONES AND THEIR ANALOGUES XLVIII. A CONVENIENT SYNTHESIS OF THE 10E,12Z- AND 10E,12E-ISOMERS OF HEXADECADIEN-1-OL AND OF HEXADECA-10E,12Z-DIENAL - COMPONENTS OF THE SEX PHEROMONE OF THE SILKWORM MOTH
Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Sokol'skaya, O. V.,Muslukhov, R. R.,et al.
, p. 668 - 673 (2007/10/02)
The 10E,12Z- and 10E,12E-isomers of hexadecadien-1-ol and of hexadeca-10E,12Z-dienal - components of the sex pheromone of the silkworm moth Bombyx mori - have been synthesized from the readilly available octa-2E,7-dien-1-ol.
HIGHLY STEREOSELECTIVE SYNTHESES OF CONJUGATED E,E- AND E,Z-DIENES, E-ENYNES AND E-1,2,3-BUTATRIENES VIA ALKENYLBORANE DERIVATIVES
Negishi, Ei-ichi,Yoshida, Takao,Abramovitch, Akiva,Lew, George,Williams, Robert M.
, p. 343 - 356 (2007/10/02)
A highly selective and potentially general methodology for the synthesis of conjugated E,E- and E,Z-dienes, E-enynes, and E-1,2,3-butatrienes via hydroboration of alkynes is reported.The observed stereoselectivity was >98-99percent.
A new synthesis of α,β-unsaturated aldehydes: Synthesis of traumatin and bombykol
Dasaradhi,Neelakantan,Jagadishwar,Bhalerao
, p. 183 - 190 (2007/10/02)
A novel conversion of an alkene to a higher homologue α,β-unsaturated aldehyde was achieved in three steps. The aldehydes were used for the synthesis of traumatin, a wound hormone and bombykol, the pheromone of bombyx mori.
AN EASY ROUTE TO INSECT PHEROMONES WITH A E-Z OR Z-E CONJUGATED DIENE STRUCTURE
Fiandanese, V.,Marchese, G.,Naso, F.,Ronzini, L.,Rotunno, D.
, p. 243 - 246 (2007/10/02)
Insect pheromones having a conjugated diene system of E-Z or Z-E configuration can be prepared with high stereoselectivity, by means of addition reactions of Z-dialkenyl cuprates to phenylthioacetylene.The alkadienyl sulphides intermediates are then subjected to a cross-coupling reaction with Grignard reagents, in the presence of a Ni(II) complex as a catalysts, leading to the desired pheromones.
