66410-24-0Relevant articles and documents
Method for preparation of Octadecadienyl acetate as major sex pheromone of cherry tree borer, Synanthedon bicingulate
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Paragraph 0057; 0069-0071, (2018/06/26)
The present invention relates to a method for producing a sex pheromone of cherry tree borer (Synanthedon bicingulata) in an attempt to control the same. More specifically, provided is a method for stereoselectively producing high purity (3E,13Z)- octadecadienyl acetate and (3Z,13Z)-octadecadienyl acetate respectively which are major sex pheromones of cherry tree borer from a cheap starting material in an efficient, simple, and economically feasible way.COPYRIGHT KIPO 2018
Synthesis and characterization of 3,13- and 2,13-octadecadienyl compounds for identification of the sex pheromone secreted by a clearwing moth, Nokona pernix
Naka, Hideshi,Nakazawa, Tomotake,Sugie, Mieko,Yamamoto, Masanobu,Horie, Yoshiteru,Wakasugi, Ryohei,Arita, Yutaka,Sugie, Hajime,Tsuchida, Koji,Ando, Tetsu
, p. 508 - 516 (2008/02/10)
Several geometrical isomers of 3,13- and 2,13-octadecadien-1-ols and their acetates were synthesized starting from 1,8-octanediol or 1,9-nonanediol utilizing acetylene coupling reactions. In addition to commercially available compounds, all geometrical isomers of each dienyl compound were analyzed by NMR and GC-MS to accumulate chemical data for studies of sex pheromones secreted from clearwing moths classified into the family Sesiidae of Lepidoptera. Although acetoxy derivatives of the 3,13- and 2,13-dienes showed almost the same mass spectra, the alcohols were distinguished by comparing the relative intensities of [M - 18]+ at m/z 248, indicating direct differentiation of the two positional isomers without derivatization. Furthermore, each geometrical isomer eluted from a high-polar GC column with a different retention time. Base on these data, a pheromone gland extract of a sesiid moth, Nokona pernix, was analyzed by GC-EAD and GC-MS, and two EAG-active components were identified, viz., the (3E,13Z)- and (3Z,13Z)-isomers of 3,13-octadecadien-1-ol in a ratio of 9:1. In the field, the synthetic compounds mixed in 9:1 ratio attracted N. pernix males well, while a single component scarcely attracted the males. The number of attracted males peaked in the middle of June, and a small second peak was observed in August.
Synthesis of (3Z,13Z)-3,13-octadecadienyl acetate - Sex pheromone of Synanthedon tenuis-using readily available C11-synthon
Narasimhan,Ganeshwar Prasad,Madhavan
, p. 99 - 101 (2007/10/03)
Synthesis of (3Z,13Z)-3,13-octadecadienyl acetate has been achieved from the readily available 10-undecen-1-ol using cheaper reagents and less number of steps. In the key step alkylation of an alkyne is performed with solid sodamide giving the product in 50% yield. The method can be easily scaled-up.
1,(ω-1)-Dienes: solvent controlled unilateral or bilateral metallation
Moret, Etienne,Desponds, Olivier,Schlosser, Manfred
, p. 83 - 91 (2007/10/02)
In hexane, i.e. under heterogeneous conditions, 1,(ω-1)-dienes readily undergo double deprotonation to give bis(allylmetal) intermediates.In tetrahydrofuran at -75 or -50 deg C, however, only monometallation occurs with dienes having chains of up to 12 carbon atoms.The practical potential of such selective monosubstitution reactions is demonstrated by two novel pheromone syntheses.
Stereoselective synthesis of (Z,Z)-3, 13-octadecadien-1-ol, (Z,Z)-3, 13-octadecadien-1-yl acetate and their (E,Z)isomers
Trehan, I R,Kad, G L,Singh, Vasundhara,Vig, Rakesh
, p. 563 - 566 (2007/10/02)
(Z,Z)-3,13-Octadecadien-1-ol (VIII), (Z,Z)-3,13-octadecadien-1-yl acetate (IX) and their corresponding (E,Z) isomers (X and XI) have been synthesized via Li2CuCl4 catalysed coupling reaction of (Z)-8-tridecylmagnesium bromide with mesylate (II) as a key step.
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.
SIMPLE AND STEREOCONTROLLED SYNTHESIS OF AN OPTIMAL ISOMERIC MIXTURE OF 3,13-OCTADECADIEN-1-YL ACETATES
Vinczer, Peter,Baan, Gabor,Juvancz, Zoltan,Novak, Lajos,Szantay, Csaba
, p. 1257 - 1270 (2007/10/02)
A simple route has been developed for the preparation of the optimal isomeric mixture of 3,13-octadecadien-1-yl acetates (ODDA) which is the active sex pheromone of many Synanthedon species.The stereocontrolled formation of double bonds have been achieved via Wittig reaction and subsequent reduction of C-C triple bond.
