65686-49-9Relevant articles and documents
Sex pheromone of Lonomia obliqua: Daily rhythm of production, identification, and synthesis
Zarbin, Paulo H. G.,Lorini, Lisete M.,Ambrogi, Bianca G.,Vidal, Diogo M.,Lima, Eraldo R.
, p. 555 - 565 (2008/04/01)
The sex pheromone of Lonomia obliqua Walker (Lepidoptera: Saturniidae) was studied in the laboratory. All female calling occurred during the scotophase. Most females (70.6%) called first within 24 hr of eclosion. Calling varied with age of female, with older (5- to 6-day-old) females calling earlier in the scotophase and for longer durations than younger (0- to 1-day-old) females. The sex pheromone gland of 1- to 3-day-old virgin females was extracted during the calling peak. A Y-olfactometer bioassay showed significant attraction of males to a filter paper containing the female gland extract. Gas chromatographic- electroantennogram detection (GC-EAD) analysis of the extract indicated the presence of at least two possible pheromone components. Gas chromatographic-mass spectrometric analysis of the major GC-EAD-active peak indicated a hexadecenyl acetate; chemical derivatization indicated Δ11 unsaturation. Synthetic samples of (E)- and (Z)-11-hexadecenyl acetate were obtained by coupling 10-bromo-1-decanol and 1-hexyne, utilizing lithium chemistry. The comparison of the retention time of dimethyl disulfide derivatives of the natural compound, to those of synthetic chemicals, confirmed the natural compound as (E)-11-hexadecenyl acetate. The minor component was identified as the related alcohol, (E)-11-hexadecenol. The ratio of the two components in female extract was 100:35. Preliminary tests of males in a Y-olfactometer showed that their response to a mixture of the two compounds was not significantly different from that to gland extract.
Use of enyne compounds in the synthesis of insect pheromones
Ishmuratov,Ishmuratova,Odinokov,Tolstikov
, p. 25 - 30 (2007/10/03)
A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.
Preparation of functionalized alkynes having internal triple bonds
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, (2008/06/13)
Functional internal alkynes are conveniently and economically prepared by dehydrohalogenating a dibromide with an alkali metal hydroxide in the presence of a phase transfer catalyst.
SYNTHESIS OF TRANS-2,CIS-13- AND TRANS-3,CIS-13-OCTADECADIEN-1-OL ACETATES, COMPONENTS OF THE SEX PHEROMONE OF SYNANTHEDON TIPULIFORMIS (LEPIDOPTERA, SISIIDAE)
Sorochinskaya, A.M.,Kovalev, B.G.
, p. 621 - 624 (2007/10/02)
The Wittig-Horner reaction of ethoxycarbonylmethylenetriphenylphosphorane or ethyl diethylphosphonoacetic acid with cis-11-hexadecenal and the modified Knoevenagel reaction of this aldehyde with malonic acid gave the ethyl ester of trans-2,cis-13-octadecadienoic acid and trans,cis-13-octadecadienoic acid, which upon reduction and acetylation were converted into trans-2,cis-13- and trans-3-cis-13-octadecadien-1-yl acetates, which are components of the sex pheromone of Synanthedon tipuliformis (Lepidoptera, Sisiidae).
INSECT PHEROMONES AND THEIR ANALOGUES XXV. SYNTHESIS OF ACETYLENIC PRECURSORS OF PHEROMONES FROM UNDECYLENIC ACID
Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Vyrypaev, E. M.,Tolstikov, G. A.
, p. 702 - 704 (2007/10/02)
The selective ozonolysis of pentadec-1-en-22-yne and heptadec-1-en-22-yne, synthesized from the readily available undecylenic acid, has given tetradec- and hexadec-11-yn-1-ols - acetylenic precursors of a number of pheromones of insects of the order Lepidoptera.
A facile synthesis of cotton bollworm (Heliothis armigera) pheromone components: (Z)-11-Hexadecenal and (Z)-9-hexadecenal
Mithran, S.,Mamdapur, V. R.
, p. 755 - 756 (2007/10/02)
(Z)-Hexadecenal (1) and (Z)-9-hexadecenal (2) have been synthesised starting from easily accessible propargyl alcohol.Alkylation of propargyl alcohol yields 3 and 4, which on acetylene-zipper reaction give terminal acetylenes (5 and 6, R'=H).Alkylation of 5 and 6 followed by depyranylation afford 7 and 8.Partial cis-hydrogenation of these with P2Ni followed by PCC oxidation give compounds 1 and 2.
INSECT PHEROMONES AND THEIR ANALOGS. XVII. SYNTHESIS OF (Z)-HEXADEC-11-ENAL AND (Z)-HEXADEC-11-EN-1-YL ACETATE
Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Tolstikov, G. A.
, p. 365 - 368 (2007/10/02)
(Z)-Hexadec-11-enal and (Z)-hexadec-11-en-1-yl acetate - components of the sex pheromone of insects of the genera Heliothis and Manestra, respectively - have been synthesized by the condensation of undec-10-enal with hex-1-yne, deoxygenation of the heptadec-1-en-12-yn-11-ol formed via the corresponding tosylate to heptadec-1-en-12-yne, and the selective oxonolysis of the latter.
Vinylic Organoboranes. 5. An Improved, Convenient Synthesis of Unsymmetrical Alkynes via Iodination of Lithium Alkynyl "Ate" Complexes of Thexylalkylborinates
Sikorski, James A.,Bhat, N. G.,Cole, Thomas E.,Wang, Kung K.,Brown, Herbert C.
, p. 4521 - 4525 (2007/10/02)
The transfer reaction induced by iodination of lithium alkynyl "ate" complexes of organoboranes represents a novel route to unsymmetrical alkynes.Several potential "blocking" groups were examined in order to achieve the selective migration of one primary alkyl group and thereby increase the efficiency of this process.Best results were obtained with the combined use of the thexyl and methoxy moieties as "blocking" groups in this reaction.The required thexylalkylborinate intermediates were conveniently prepared in high yield from thexylchloroborane via hydroboration and methanolysis.Subsequent complexation with an appropriate lithium alkyne, followed by iodination, produced the desired unsymmetrical alkyne in high yield.Minimum amounts of the product resulting from competitive migration of the thexyl group were observed.Under these conditions, an efficient utilization of a primary alkyl group in this transfer reaction is achieved.Furthermore, the high tolerance of thexylchloroborane toward many functional groups and its high regioselectivity in terminal alkene hydroboration produces intermediates that are particularly useful for the synthesis of insect pheromones and not readily accessible via conventional organometallic procedures.
SYNTHESIS OF (Z)-TETRADEC-11-EN-1-OL AND (Z)-HEXADEC-11-EN-1-OL FROM DODECANE-1,12-DIOL
Zakharkin, L. I.,Guseva, V. V.
, p. 733 - 736 (2007/10/02)
A method have been developed for obtaining (Z)-tetradec-11-en-1-ol and (Z)-hexadec-11-en-1-ol via dodec-11-yn-1-ol.
