75539-65-0Relevant academic research and scientific papers
Insect pheromones and their analogs LIX. A new method for the synthesis of components of the sex pheromones of insects of the genus Malacosoma
Kukovinets,Kasradze,Salimova,Odinokov,Galin,Fedorov
, p. 358 - 360 (2007/10/03)
A new method has been developed for the synthesis of the main components of the sex pheromones of insects of the Malacasoma genus that is based on the selective transformation of the product of the partial ozonolysis of cyclohexa-1,4-diene - methyl 6-oxohex-4E-enoate.
OZONOLYSIS OF ALKENES AND THE REACTIONS OF POLYFUNCTIONAL COMPOUNDS LII. SELECTIVE OZONOLYSIS OF (E)-2,7-OCTADIENAL AND (E)-3,7-DIMETHYL-2,6-OCTADIENAL IN THE SYNTHESIS OF INSECT PHEROMONES
Odinokov, V. N.,Ishmuratov, G. Yu.,Sokol'skaya, O. V.,Galeeva, R. I.,Muslukhov, R. R.,Tolstikov, G. A.
, p. 19 - 23 (2007/10/02)
The partial ozonolysis of (E)-2,7-octadienal and (E)-3,7-dimethyl-2,6-octadienal led to (E)-7,7-dimethoxy-2-heptenal and (E)-1,6-diacetoxy-3-methyl-2-hexene.The products were used for the synthesis of (5E,7Z)-5,7-dodecadienal and the corresponding alcohol and acetate , 4,8-dimethyldecanal , and (E)-4-methyl-1,1-dimethoxy-8-oxo-4-nonene .
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.
