86252-74-6Relevant academic research and scientific papers
Stereospecific synthesis of (2E,13Z)-2,13-octadecadienyl acetate, the sex pheromone component of the Lepidoptera species
Grodner, Jacek
, p. 919 - 924 (2006)
The main component of the sex pheromone of many lepidopteran pests, (2E,13Z)-2,13-octadecadienyl acetate (1), has been synthesized following a simple route using 12-(2-tetrahydropyranyloxy)-1-dodecyne (2) as the starting material. Copyright Taylor & Francis Group, LLC.
Synthesis from 10-undecenoic acid of octadeca-2E,13Z-dienylacetate, a component of the sex pheromones of Synanthedon tipuliformis and Zenzera pyrina
Ishmuratov,Botsman,Botsman,Yakovleva,Kharisov,Tolstikov
, p. 207 - 209 (2007/10/03)
A new synthesis of octadeca-2E,13Z-dienylacetate from 10-undecenoic acid is developed by constructing the carbon framework of the pheromone in the key step and introducing the 2E double bond by Doebner condensation of hexadec-11-ynal and malonic acid.
A convergent and highly efficient synthesis of (E,Z)-2,13-octadecadienyl acetate and (E,Z)-3,13-octadecadienyl acetate, components of the sex pheromone of the Leopard Moth Zeuzera pyrina, through sulfones
Capdevila, Anna,Prasad, Attaluri R.,Quero, Carmen,Petschen, Ine?s,Bosch, Maria P.,Guerrero, Angel
, p. 845 - 848 (2008/02/09)
(equation presented) A new, convergent synthesis of (E,Z)-2,13-octadecadienyl acetate (1) and (E,Z)-3,13-octadecadienyl acetate (2), the two key components of the leopard moth Zeuzera pyrina, from 2-chloromethyltetrahydrofuran in good overall yields and stereomeric purity is reported. The synthesis of both components utilizes the common intermediate sulfone 12 as a convenient building block to be coupled with iodoacetylenic derivatives 9 or 17 in the key step.
Chemistry of natural compounds and bioorganic chemistry a convergent synthesis of octadeca-2E,13Z-dienyl acetate, a pheromone component of Synanthedon tipuliformis C
Ishmuratov,Yakovleva,Kharisov,Kunafina,Gorobets,Kuchin,Tolstikov
, p. 1465 - 1467 (2007/10/03)
A convergent synthesis of octadeca-2E,13Z-dienyl acetate, a pheromone component of Synanthedon tipuliformis C., has been developed. The synthesis is based on cross-coupling of 8-iodooct-2E-en-1-ol THP ether with dec-57-enyl bromide catalyzed by CuBr.
A simple, cost effective synthesis of E,Z-2,13-octadecadienyl acetate, a major sex pheromone component of lepidopteran pests
Narasimhan, S.,Mohan, H.,Madhavan, S.
, p. 531 - 534 (2007/10/02)
A simple, cost effective synthesis of E,Z-2,13-octadecadienyl acetate (1), a major sex pheromone component of many lepidopteran pests, has been achieved in optimum number of steps using cheaper raw meterials.The strategy provides the target compound in 43percent overall yield, and can be scaled up easily.
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).
A CONVENIENT SYNTHESIS OF 2,13- AND 3,13-OCTADECADIENYL ACETATES, SEX PHEROMONE COMPONENTS OF THE Synanthedon SPECIES
Hoskovec, Michal,Saman, David,Koutek, Bohumir
, p. 2270 - 2281 (2007/10/02)
The sex pheromone components of several Synanthedon species, 2,13- and 3,13- octadecadienyl acetates (Ic, Id, IIc, IId), have been synthesized following the acetylenic route of chain elongation.Starting from ω-alkyn-1-ols III, the final compounds were constructed in five steps in about 30percent overall yields.Transformation of triple bond containing intermediates into the corresponding (Z)- and (E)-olefins was achieved either by hydrogenation over the P2-Ni catalyst or by using a dispersion of sodium in toluene.The title pheromones were generated in more than 97percent stereoisomeric purity. 1H and 13C NMR data of all derivatives are included.
Synthesis of (2E, 13Z)-2, 13-octadecadien-1-yl acetate
Sharma,Thapar,Gupta
, p. 657 - 658 (2007/10/02)
(2E, 13Z)-2, 13-Octadecadien-1-yl acetate (1), a new pheromone from the moths of Sesiidae family has been synthesized employing copper (I) and copper (II) catalyzed coupling reactions as the key steps.
SYNTHESIS OF THE ACETATE OF OCTADECA-trans-2,cis-13-DIEN-1-OL, A COMPONENT OF THE SEX PHEROMONES OF synanthedon tipuliformis AND Zeuzera pyrina
Sorochinskaya, A. M.,Kovalev, B. G.
, p. 228 - 230 (2007/10/02)
A new synthesis of the acetate of octadeca-trans-2,cis-13-dien-1-ol based on the alkylation of propargyl alcohol with pentadec-cis-10-enyl bromide, obtained from the readily accessible decamethylene bromohydrin, has been effected.
A New Highly Stereospecific Synthesis of (E,Z)-2,13-octadecadienyl Acetate, a Sex Pheromone Component of Some Lepidoptera Species.
Ramiandrasoa, F.,Descoins, C.
, p. 2703 - 2712 (2007/10/02)
The synthesis of the Z moiety of the title compound has been achieved by carbocupration of acetylene followed by alkylation with the appropriate organozinc reagent in the presence of catalytic Pd0.The coupling of this intermediate with protecte
