75983-34-5Relevant academic research and scientific papers
Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone
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, (2019/01/08)
The invention discloses a synthetic method for an attractant component namely a cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone. With the synthetic method provided by the invention,5-hexyne-1-ol and 3, 4-dihydro-2H-pyran used as starting materials are successively subjected to an addition reaction, a condensation reaction, an elimination reaction, a hydrogenation reaction, a deprotection reaction and a derivatization reaction to obtain the cis,trans-5,7-dodecadiene derivative. The synthetic method provided by the invention has the advantages of short route, high reaction yield in each step, simple operation and convenience in mass production.
Efficient synthesis of (5Z,7E)-Dodecadienal, the sex pheromone of the european pine moth dendrolimus pini
T?t?s, ?tefania,Vasian, Iuliana,Gorgan, Monica,T?t?s, Róbert,Lar, Claudia
, p. 315 - 319 (2018/10/20)
Efficient synthesis of (5Z,7E)-dodecadienal, the sex pheromone of European pine moth Dendrolimus pini, was stereoselectively accomplished via Pd- and Fe- catalyzed cross-coupling reactions in the key steps. The very simple and practical method developed herein provides a general synthetic approach to other (Z,E)-diene compounds.
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.
Stereoselective synthesis of Z, E conjugated dienes: Application to the synthesis of insect sex pheromones
Vig,Sharma,Kapur,Thapar,Gupta
, p. 606 - 610 (2007/10/02)
Stereoselective synthesis of insect pheromone components 1-5, p possessing Z,E conjugated diene system has been developed using 1,3-enynes (generated by the in situ alkylation of dianion of prop-2-yn-1-ol followed by Horner-Witting reaction) as precursors.
SYNTHESIS OF INSECT ATTRACTANTS (SEX ATTRACTANTS). VIII. STEREOSELECTIVE SYNTHESIS OF FOUR ISOMERS OF 5,7-DODECADIEN-1-OL AND THEIR ACETATES AND ALDEHYDES, COMPONENTS OF THE SEX PHEROMONES OF INSECTS OF THE Lasiocampidae (Lepidoptera) FAMILY
Kovalev, B. G.,Rastegaeva, V. M.,Kurts, A. L.,Bundel', Yu. G.
, p. 1632 - 1638 (2007/10/02)
A new method is proposed for the stereoselective synthesis of four stereoisomers of 5,7-dodecadien-1-ol and their acetates and aldehydes on the basis of the Wittig reaction. 7-(2-Tetrahydropyranyloxy)-2-heptyn-1-ol was obtained by the alkylation of 2-propyn-1-ol with 2-(4-bromobutoxy)tetrahydropyran.By hydrogenation in the presence of colloidal nickel catalyst or by reduction with lithium aluminum hydride it was converted into the Z and E isomers respectively of 7-(2-tetrahydropyranyloxy)-2-hepten-1-ol.Oxidation of the alcohol group in the above-mentioned hydroxy acetals led to the corres ponding aldehydes, which then entered into the Wittig reaction with pentylidenetriphenylphosphorane under the conditions for the formation of a double bond with a specific configuration of the isomers (Z and E).Subsequent removal of the tetrahydropyranyl protection of the alkyl group in the Wittig reaction products gave 5,7-dodecadien-1-ols, which were converted into the corresponding acetates of the aldehydes by acetylation of oxidation.The products are components of the sex pheromones of insects of the Lasiocampidae family.
Mass Spectra of Dodecadienic Compounds with a Conjugated Double Bond, Lepidopterous Sex Pheromones
Ando, Tetsu,Katagiri, Yoshio,Uchiyama, Masaaki
, p. 413 - 422 (2007/10/02)
All geometrical isomers of 5,7-, 6,8-, 7,9-, 8,10- and 9,11-dodecadien-1-ols, and their acetates and aldehyde derivatives were analyzed by electron impact mass spectrometry.The abundance of molecular ion (M(1+)) was observed in every spectrum, and the relative intensity of M(1+) tended to be strong if the compound possessed an (E)-double bond(s).In addition to M(1+), (1+) (alcohols) and (1+) (acetates), every dienic compound showed typical series of CnH(2n-2)(1+)CnH(2n-5)(1+) with abundance maxima around C4, C5, C6 or C7.Each double bond positional isomer characteristically yielded different ion peaks in the series, which were useful for its distinction from other isomers.These results indicate that the chemical structure of a natural pheromone of Lepidoptera is easily deduced successfully by GC-MS analysis if it is a conjugated dienic pheromone.
