54364-62-4

Usage

Uses

Used in Pest Control:
(7Z,9E)-dodeca-7,9-dienyl acetate is used as a sex pheromone for the bud borer Crocidosema Aporema. It serves as a chemical attractant to lure male insects towards female counterparts, enabling mating and reproduction. By utilizing this pheromone in pest control strategies, it is possible to disrupt the mating process and reduce the population of these pests, ultimately protecting crops and agricultural resources.
Used in Ecological Research:
(7Z,9E)-dodeca-7,9-dienyl acetate is also used in the study of the effect of sex pheromone emission on the attraction of Lobesia Botrana, a species of moth. Researchers employ (7Z,9E)-dodeca-7,9-dienyl acetate to investigate the behavioral and ecological aspects of these insects, including their mating habits, population dynamics, and interactions within their ecosystems. This information can be crucial for developing effective pest management strategies and understanding the role of these species in their respective environments.

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 217, 1988 DOI: 10.1016/S0040-4039(00)80057-X

InChI:InChI=1/C14H24O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h10-13H,3-9H2,1-2H3

Upstream product

• 54364-60-2 (7E,9Z)-dodeca-7,9-dien-1-ol 
• 108-24-7 acetic anhydride 
• 6228-47-3 n-propyltriphenylphosphonium bromide 
• 72553-55-0 (E)-8-Formyl-7-octensaeure-methylester 
• 127-08-2 potassium acetate 
• 115932-80-4 9-chloro-(E)-2-nonen-1-al 
• 115932-83-7 9-bromo-(2E)-2-nonen-1-al 
• 113093-79-1 7(E),9(Z)-1-tert-butoxy-7,9-dodecadiene 
• 154556-91-9 (7E,9Z)-dodec-7,9-dien-1-ol 
• 76934-43-5 (7E,9Z)-2-((dodec-7,9-dien-1-yl)oxy)tetrahydro-2H-pyran 
• 108377-84-0 C₄H₇BrZn 
• 94742-72-0 1-iodo-(E)1-octen-8-yl acetate 
• 75-36-5 acetyl chloride 
• 50375-98-9 (Z)-2-pentenylidene triphenylphosphorane 

Relevant academic research and scientific papers

A CONVENIENT PREPARATION OF TRANS (OR CIS)-1-CHLOROALKENES FROM TRANS (OR CIS)-1,2-DICHLOROETHYLENE: A NEW SYNTHESIS OF THE SEX PHEROMONE OF LOBESIA BOTRANA

Trans (or cis)-dichloroethylene leads to trans (or cis)-1-chloroalkanes when treated with Grignard reagents and to trans (or cis)-1-chloro-1-en-3-ynes when treated with terminal acetylenes.A symple synthesis of (7E, 9Z)-dodecadien-1-yl acetate has been realized.

A NEW STRATEGY FOR THE SYNTHESIS OF THE PHEROMONES of Lobesia botrana and Bombyx mori

Opening of epoxysilanes by alkenyl cuprates reagents in the presence of BF3*Et2O afford β-hydroxysilanes which after basic or acidic treatment give the title pheromones.

THE HYDROALUMINATION OF ω-TERBUTOXY ALKYNES AN EASY ACCESS TO ω-HYDROXY ALKENYL IODIDES APPLICATION TO THE SYNTHESIS OF DIENIC INSECT PHEROMONES

In contrast to classically protected ω-hydroxy alkynes, ω-terbutoxy alkynes undergo smooth hydroalumination with DIBAL-H.The obtained E or Z alkenyl alanes are iodinated leading to E or Z alkenyl iodides.The ω-terbutoxy group is easily converted into an acetate.The latter compounds are useful synthons for the synthesis of insect pheromones as examplified with two cases.

Eco-Friendly and Industrially Scalable Synthesis of the Sex Pheromone of Lobesia botrana. Important Progress for the Eco-Protection of Vineyard

A one-pot synthesis of the pheromone of Lobesia botrana is described. The procedure allows an efficient and economical access to this product which is used for the protection of vineyards.

Tellurium in organic synthesis: an approach to the synthesis of (Z,E)-dienic precursors of insect pheromones

A simple and straightforward route to (Z,E)-dienic precursors of insect pheromones was developed. The route features a cross-coupling of a (Z,E)-dienic telluride with an alkyl Lipshutz cuprate.

Method for preparing trans -7 and cis -9 - dodecadiene acetate

The invention discloses a method for preparing trans -7 and cis -9 - dodecadiene acetate, which comprises (1) adding 1 - 1 dichloroethylene in 2 - butyne tetrahydrofuran solution. The metal palladium compound, cuprous iodide and diisopropylamine undergo a coupling reaction to obtain 1 - chlorine -3 - yne -1 - hexene. (2) 20 °C (ClMgO) Under stirring, at CH. 2 )6 In MgCl, hexamethylphosphoric acid triamide and ferric acetyl acetonate are sequentially added, 1 - chlorine -3 - yne -1 - hexene is added dropwise to obtain the trans 7 - dodecene -9 - alkynol. (3) Zn powder was added to trans 7 - dodecene -9 - alkynol, stirred to obtain trans 7, cis 9 - dodecadienol, acetic anhydride and pyridine were added and stirred to obtain trans -7, cis -9 - dodecadiene acetate. The method provided by the invention is cheap and wide in source; the method has the advantages of short synthesis period, less steps, high yield, good stereoselectivity and simple post-treatment.

Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System

A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.

SYNTHESIS OF CONJUGATED DIENE PHEROMONES AND RELATED COMPOUNDS

Methods for preparing conjugated dienes are described. An α,β-unsaturated E olefin intermediate may be prepared via cross-metathesis using a catalyst comprising a transition metal (e.g., ruthenium), a first carbene ligand (e.g., a substituted indenylidene) and an N-heterocyclic carbene ligand (e.g., an imidazolidinylidene). The catalyst further includes a phenylphosphine ligand, a tri(isopropoxy)phosphine ligand, a dimethylsulfoxide ligand, an acetonitrile ligand, or a pyridine ligand. Following the cross metathesis-step, the α,β-unsaturated aldehyde intermediate may be converted to the conjugated diene product via reaction with a phosphonium ylide. Products obtained via the methods of the disclosure include (7E,9Z)-dodeca-7,9-dien-1-yl acetate, a pheromone produced by Lobesia botrana (European grapevine moth), and other insect pheromones.

METHOD FOR PRODUCING COMPOUND HAVING CONJUGATED DIENE STRUCTURE

PROBLEM TO BE SOLVED: To provide a method capable of industrially producing a conjugated diene or a conjugated triene in a short process from a raw material which is easy to obtain and handle. SOLUTION: A conjugated diene is produced from a 3-alkenal via reactions of the following first step, second step, and third step in this order: the first step of reacting a Grignard reagent with the 3-alkenal to obtain a homoallylic alcohol; a second step of reacting an esterification reagent or a halogenation reagent with the homoallylic alcohol to obtain a sulfonic ester or a halogenated product; and a third step of having a base act on the sulfinic acid ester or the halogenated product to cause an elimination reaction. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

A acetic acid 7 E, 9 Z - twelve carbon two alkene ester synthesis method (by machine translation)

The present invention provides a kind of acetic acid 7 E, 9 Z - twelve carbon two alkene ester synthesis method, which belongs to the technical field of organic synthesis. The present invention provides a method to synthesis of 1, 5 - dibromo-pentane as the starting material for the preparation of 1, 7 - heptyl glycol, then single-esterification reaction to produce acetic acid 7 - hydroxy heptyl esters, acetic acid 7 - hydroxy heptyl esters obtained after the oxidation of acetic acid 7 - [...], acetic acid 7 - [...] 1st Wittig reagent occurs with the 1st Wittig reaction, by hydrolytic reaction, to obtain acetic acid 9 - oxo - 7 E - [...], acetic acid 9 - oxo - 7 E - [...] 2nd Wittig reagent occurs with the 2nd Wittig reaction, to obtain acetic acid 7 E, 9 Z - [...], the route the required raw materials are cheap and easy to get, only five-step to get the final product. (by machine translation)