78350-11-5Relevant academic research and scientific papers
Synthesis of (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof
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Paragraph 0039-0041, (2019/03/28)
The invention belongs to the technical field of insect pheromone synthesis, and discloses a new method for synthesizing (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof.The method takes propynol as an initial raw material to be subjected to coupling with 1-bromobutane to generate 2-heptyne-1-alcohol, triple bond is reduced to be E-type double bond through LiAlH4, 2-heptyne-1-alcohol is oxidized to be olefine aldehyde through PDC, olefine aldehyde reacts with a Wittig reagent (5-ethyoxyl-5-oxopentyl)triphenyl phosphonium bromide to produce (5Z,7E)-dodecane-5,7-dienoic acid ethyl ester which is reduced by LiAlH4 to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol, (5Z,7E)-dodecane-5,7-diene-1-alcohol reacts with acetyl chloride and propionyl chloride finally to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol acetate and (5Z,7E)-dodecane-5,7-diene-1-alcohol propionate. The method utilizes LiAlH4 to reduce the triple bond to be the E-type double bond, and utilizes theWittig reaction of the Wittig reagent with the tail end provided with ester group and aldehyde to directly build the Z-type double bond, the synthesis route is simple, convenient and efficient, and the reaction condition is moderate and environmentally friendly.
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.
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.
STEREOSPECIFIC SYNTHESIS OF (Z)-13-HEXADECEN-11-YN-1-YL ACETATE THE SEX PHEROMONE OF THE PROCESSIONARY MOTH, AND OF (5Z,7E)-5,7-DODECADIEN-1-OL, A SEX PHEROMONE COMPONENT OF THE FOREST TENT CATERPILLAR
Rossi, Renzo,Carpita, Adriano
, p. 287 - 290 (2007/10/02)
(Z)-13-hexadecen-11-yn-1-yl acetate (2), the sex pheromone of Thaumetopoea pytyocampa, and (5Z,7E)-5,7-dodecadien-1-ol (3), sex pheromone component of Malacosoma disstria, have been prepared in high chemical and stereoisomeric purity by synthetic schemes involving the stereospecific coupling of ω-functionalized 1-alkynes with (Z)- or (E)-1-iodo-1-alkenes in the presence of a catalytic amount of (PPh3)4Pd and CuI, under phase transfer conditions.
