cas 50767-79-8, Z,E-9,11-TETRADECADIENYL ACETATE

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SYNTHESIS WITH SULFONES (noXXXI): THE STEREOSPECIFIC REDUCTION OF 2-BENZENESULFONYL-1,3 DIENES TO CONJUGATED Z,E-DIENES. SYNTHESIS OF (9Z,11E)-9,11-TETREDECADIENYL ACETATE.
The stereospecific reduction of 2-phenylsulfonyl-1,3-dienes 1i to conjugated EZ dienes 2 catalysed by transition metal complexes in the presence of n-butylmagnesium chloride is described.This method is illustrated by the synthesis of the pheromone of Spodoptera littoralis : 9Z,11E-tetradecadien-1-yl acetate 8, R = Ac.
Cuvigny, T.,Fabre, J. L.,Herve, du Penhoat C.,Julia, M.
p. 4319 - 4322
(1983)
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A kind of 9Z, 11E - tetradecenoic dienol acetate method for the synthesis of
The invention relates to a synthesis method of prodenia litura sex pheromone main component (9Z,11E)-tetradecadienol acetate. The method comprises the following steps: by using 7-bromine-(4Z,6E)-heptadienal and 1,5-pentanediol as initial raw material, firstly reducing 7-bromine-(4Z,6E)-heptadienal as 7-bromine-(4Z,6E)-heptadienol; performing Kumada cross coupling reaction on 7-bromine-(4Z,6E)-heptadienol and ethyl magnesium bromide to obtain (4Z,6E)-nonadienol; performing chlorination through thionyl chloride to obtain (3E,5Z)-9-chlorine nonadienol; reacting (3E,5Z)-9-chlorine nonadienol with magnesium to prepare a corresponding Grignard reagent; and coupling (3E,5Z)-9-chlorine nonadienol with 2-(5-bromo pentyloxy)-tetrahydropyrane prepared by 1,5-pentanediol under the catalysis of lithium tetrachlorocuprate to obtain 2-(9Z,11E-tetradecadiallyloxy)-tetrahydropyrane, and finally reacting with acetylchloride to obtain a target product (9Z,11E)-tetradecadienol acetate. The method provided by the invention has the advantages of available and cheap raw material, simple synthesis line, moderate reaction condition, high yield and low cost, and is convenient and safe to operate.
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(2017/02/28)

Z-Selective Cross-Metathesis and Homodimerization of 3E-1,3-Dienes: Reaction Optimization, Computational Analysis, and Synthetic Applications
Olefin metathesis reactions with 3E-1,3-dienes using Z-selective cyclometalated ruthenium benzylidene catalysts are described. In particular, a procedure for employing 3E-1,3-dienes in Z-selective homodimerization and cross-metathesis with terminal alkenes is detailed. The reaction takes advantage of the pronounced chemoselectivity of a recently reported ruthenium-based catalyst containing a cyclometalated NHC ligand for terminal alkenes in the presence of internal E-alkenes. A wide array of commonly encountered functional groups can be tolerated, and only a small excess (1.5 equiv) of the diene coupling partner is required to achieve high yields of the desired internal E,Z-diene cross-metathesis product. Computational studies have been performed to elucidate the reaction mechanism. The computations are consistent with a diene-first pathway. The reaction can be used to quickly assemble structurally complex targets. The power of this cross-metathesis reaction is demonstrated by the concise syntheses of two insect pheromones.
Luo, Shao-Xiong,Cannon, Jeffrey S.,Taylor, Buck L. H.,Engle, Keary M.,Houk,Grubbs, Robert H.
supporting information
p. 14039 - 14046
(2016/11/06)

Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)
Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9- dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11- tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding the (Z,Z)-7,9- dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.
Zhu, Junwei,Ryrholm, Nils,Ljungberg, Hakan,Hansson, Bill S.,Hall, David,Reed, Darwin,Loefstedt, Christer
p. 1505 - 1526
(2007/10/03)

Facile synthesis of (9Z,11E)-tetradecadien-1-yl acetate, sex pheromone component of some lepidopterous pests
The bifunctionality of propargyl alcohol has been exploited to synthesise the title conjugated dienic pheromone using some operationally simple reactions.
Chattopadhyay, A,Mamdapur, V R
p. 260 - 261
(2007/10/02)

Stereoselective synthesis of Z, E conjugated dienes: Application to the synthesis of insect sex pheromones
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.
Vig,Sharma,Kapur,Thapar,Gupta
p. 606 - 610
(2007/10/02)

Stereoselective Synthesis of a Potential Sex Pheromone of Stenoma Cecropia (Lepidoptera)
A convenient preparation of (Z,E) 9,11- and (Z,Z) 9,11-tetradecadien-1-yl and (9Z) 9,11-tetradecenyn-1-yl acetate, alcohol and aldehyde with 99.5percent stereoisomeric purity is described.The key step of this synthesis is the carbocupration of acetylene followed by palladium catalyzed cross coupling rection with the appropriate zinc reagent.
Ramiandrasoa, F.,Tellier, F.
p. 333 - 344
(2007/10/02)

PREPARATION OF 1,3-DIENES, ITS APPLICATION TO THE SYNTHESIS OF (Z,E)-9,11-TETRADECADIENYL ACETATE AND (E,E)-10,12-HEXADECADIENAL: SEX PHEROMONES OF COTTON PESTS
E-2-Penten-4-yn-1-ol (3) has been utilized as a source for 1,3-diene systems by employing lithium amide induced alkylation, and curpous iodide catalysed Grignard coupling reaction as key steps.Its application for the synthesis of (Z,E)-9,11-tetradecadienyl acetate and (E,E)-10,12-hexadecadienal is described.
Yadav, J S,Deshpande, Prasad K,Reddy, E Rajarathnam
p. 125 - 134
(2007/10/02)

AN EASY ROUTE TO INSECT PHEROMONES WITH A E-Z OR Z-E CONJUGATED DIENE STRUCTURE
Insect pheromones having a conjugated diene system of E-Z or Z-E configuration can be prepared with high stereoselectivity, by means of addition reactions of Z-dialkenyl cuprates to phenylthioacetylene.The alkadienyl sulphides intermediates are then subjected to a cross-coupling reaction with Grignard reagents, in the presence of a Ni(II) complex as a catalysts, leading to the desired pheromones.
Fiandanese, V.,Marchese, G.,Naso, F.,Ronzini, L.,Rotunno, D.
p. 243 - 246
(2007/10/02)

A Stereospecific Synthesis of All Four Isomers of 9,11-Tetradecadienyl Acetate Using a General Method Applicable to 1,3-Dienes
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Bjoerkling, Fredrik,Norin, Torbjoern,Unelius, C. Rikard
p. 292 - 294
(2007/10/02)

Stereoselective synthesis of (7E,9Z)-7,9-dodecadien-1-yl acetate, (E)-9,11-dodecadien-1-yl acetate, and of (9Z,11E)-9,11-tetradecadien-1-yl acetate by palladium-catalyzed reactions
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Rossi,Carpita,Quirici
p. 2617 - 2623
(2007/10/02)

NEW SYNTHESIS OF THE SEX PHEROMONE OF THE EGYPTIAN COTTON LEAFWORM, SPODOPTERA LITTORALIS.
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Ratovelomana, V.,Linstrumelle, G.
p. 917 - 924
(2007/10/02)

Pheromones. XXXIV. Synthesis of conjugated-unsaturated lepidoptera pheromones of analogues
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Bestmann,Suess,Vostrowsky
p. 2117 - 2138
(2007/10/02)

SYNTHESIS OF LOBESIA BOTRANA AND SPODOPTERA LITTORALIS NATURAL SEX-ATTRACTANTS
Starting from the coupling reaction of alkyl cuprates with 1-alkynyl-2-propenyl acetates, the title compounds were preparated by short convenient syntheses.
Cassani, G.,Massardo, P.,Piccardi, P.
p. 3497 - 3498
(2007/10/02)