72922-18-0Relevant academic research and scientific papers
PROCESS FOR PREPARING A FORMYLALKENYL ALKOXYMETHYL ETHER COMPOUND AND PROCESSES FOR PREPARING CONJUGATED DIENE COMPOUNDS FROM THE SAME
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Paragraph 0189-0194, (2021/10/02)
The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R3CH2OCH2O(CH2)aCH═CHCHO (2), wherein R3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R3CH2OCH2O(CH2)aCH═CHCH(OR1)(OR2) (1), wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, having 2 to 10 carbon atoms; and R3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).
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.
Systematic Syntheses and Charactarization of Dodecadien-1-ols with Conjugated Double Bond, Lepidopterous Sex Pheromones
Ando, Tetsu,Kurotsu, Yuichi,Kaiva, Mieko,Uchiyama, Masaaki
, p. 141 - 148 (2007/10/02)
Four geometrical isomers of 5,7-, 6,8-, 7,9- and 8,10-dodecadein-1-ols were systematically synthesized by two routes.One involved the Wittig reaction between (E)-2-alkenal and a phosphorane with an appropriate carbon chain, and yielded a mixture of (E,Z)- and (E,E)-isomers in a ratio of ca. 3:2.The other route comprised of the Wittig reaction of a 2-alkynal and the stereoselective reduction of the triple bond to a (Z)-double bond via hydroboration with dicyclohexylborane to give a mixture of (Z,Z)- and (Z,E)-isomers in a ratio of 6:1 10:1.Both the mixtures were separately chromatographed on a silica gel column impregnated with silver nitrate to give four geometrically pure isomers.With 9,11-diene they were analysed by GC on a capillary column, HPLC, silver nitrate impregnated TLC, and 13C NMR.
