73416-71-4

Usage

Uses

Used in Pheromone Production:
(5Z,7E)-5,7-Dodecadien-1-ol is used as a key component in the production of female sex pheromones for the pine caterpillar moth, Dendrolimus kikuchii Matsumura. This application takes advantage of the compound's ability to mimic natural pheromones, which can be utilized in pest control strategies to manage and reduce the population of these moths, thereby protecting forests and agricultural crops from damage.
Used in Chemical Ecology:
In the field of chemical ecology, (5Z,7E)-5,7-Dodecadien-1-ol is used as a research tool to study the chemical communication and mating behaviors of various insect species. Understanding the role of (5Z,7E)-5,7-Dodecadien-1-ol in pheromone production can provide valuable insights into the ecological interactions between different species and their environments.
Used in Fragrance Industry:
Due to its unique scent profile, (5Z,7E)-5,7-Dodecadien-1-ol can be used as a component in the fragrance industry to create natural and complex scents for perfumes, cosmetics, and other scented products. Its ability to evoke specific olfactory responses makes it a valuable addition to the palette of fragrance chemists.
Used in Agricultural Pest Control:
(5Z,7E)-5,7-Dodecadien-1-ol can be employed in the development of pheromone-based pest control strategies, which involve the use of synthetic pheromones to disrupt the mating behavior of target insect pests. This approach can be an effective and environmentally friendly alternative to traditional chemical pesticides, reducing the impact on non-target organisms and the environment.

Synthesis Reference(s)

Synthesis, p. 674, 1986 DOI: 10.1055/s-1986-31746Tetrahedron Letters, 30, p. 243, 1989 DOI: 10.1016/S0040-4039(00)95171-2

Upstream product

• 1720-37-2 2-(hex-5-yn-1-yloxy)tetrahydro-2H-pyran 
• 693-02-7 hex-1-yne 
• 90108-05-7 1-tert-butyldimethylsiloxy-8-methylthiododec-5-yne 
• 83085-84-1 <5-(acetyloxy)pentyl>triphenylphosphonium bromide 
• 1220779-79-2 12-(tetrahydro-2H-pyran-2-yloxy)dodec-7-yn-6-ol 
• 1002-36-4 hep-2-yn-1-ol 
• 130333-92-5 (5Z,7E)-ethyl dodecyl-5,7-dienoate 
• 78350-11-5 (5Z,7E)-5,7-dodecadien-1-yl acetate 
• 17421-51-1 (E)-1-trimethylstannyl-1-hexene 
• 132716-07-5 (Z)-6-iodo-5-hexene-1-ol 
• 65960-08-9 tridec-5t-en-7-yne 
• 130592-52-8 ethyl (E)-10-(tetrahydro-2H-pyran-2-yloxy)dec-2-en-5-ynoate 
• 130592-54-0 (E)-9-(Tetrahydro-pyran-2-yloxy)-non-2-en-4-yn-1-ol 
• 130592-56-2 (2E,4Z)-9-(Tetrahydro-pyran-2-yloxy)-nona-2,4-dien-1-ol 

Downstream Products

• 78350-11-5 (5Z,7E)-5,7-dodecadien-1-yl acetate 
• 83959-30-2 (5Z,7E)-dodec-5,7-dien-1-yl propionate 
• 75983-34-5 (5Z,7E)-5,7-dodecadienal 

Relevant academic research and scientific papers

An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis

The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. Here we report Z-selective semihydrogenation of alkynes with ethanol via a coordination-induced ionic monohydride mechanism. The EtOH-coordination-driven Cl- dissociation in a pincer Ir(III) hydridochloride complex (NCP)IrHCl (1) forms a cationic monohydride, [(NCP)IrH(EtOH)]+Cl-, that reacts selectively with alkynes over the corresponding Z-alkenes, thereby overcoming competing thermodynamically dominant alkene Z-E isomerization and overreduction. The challenge for establishing a catalytic cycle, however, lies in the alcoholysis step; the reaction of the alkyne insertion product (NCP)IrCl(vinyl) with EtOH does occur, but very slowly. Surprisingly, the alcoholysis does not proceed via direct protonolysis of the Ir-C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl- ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)-H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting the alcoholysis. The 1-amine-EtOH catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility, as demonstrated by Z-selective reduction of all alkyne classes, including challenging enynes and complex polyfunctionalized molecules. Comparison with a cationic monohydride complex bearing a noncoordinating BArF- ion elucidates the beneficial role of the Cl- ion in controlling the stereoselectivity, and comparison between 1-amine-EtOH and 1-NaOtBu-EtOH underscores the fact that this base variable, albeit in catalytic amounts, leads to different mechanisms and consequently different stereoselectivity.

Synthesis of (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof

The invention belongs to the technical field of insect pheromone synthesis, and discloses a new method for synthesizing (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof.The method takes propynol as an initial raw material to be subjected to coupling with 1-bromobutane to generate 2-heptyne-1-alcohol, triple bond is reduced to be E-type double bond through LiAlH4, 2-heptyne-1-alcohol is oxidized to be olefine aldehyde through PDC, olefine aldehyde reacts with a Wittig reagent (5-ethyoxyl-5-oxopentyl)triphenyl phosphonium bromide to produce (5Z,7E)-dodecane-5,7-dienoic acid ethyl ester which is reduced by LiAlH4 to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol, (5Z,7E)-dodecane-5,7-diene-1-alcohol reacts with acetyl chloride and propionyl chloride finally to obtain (5Z,7E)-dodecane-5,7-diene-1-alcohol acetate and (5Z,7E)-dodecane-5,7-diene-1-alcohol propionate. The method utilizes LiAlH4 to reduce the triple bond to be the E-type double bond, and utilizes theWittig reaction of the Wittig reagent with the tail end provided with ester group and aldehyde to directly build the Z-type double bond, the synthesis route is simple, convenient and efficient, and the reaction condition is moderate and environmentally friendly.

Synthetic method for attractant component namely cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone

The invention discloses a synthetic method for an attractant component namely a cis,trans-5,7-dodecadiene derivative in Dendrolimus sex pheromone. With the synthetic method provided by the invention,5-hexyne-1-ol and 3, 4-dihydro-2H-pyran used as starting materials are successively subjected to an addition reaction, a condensation reaction, an elimination reaction, a hydrogenation reaction, a deprotection reaction and a derivatization reaction to obtain the cis,trans-5,7-dodecadiene derivative. The synthetic method provided by the invention has the advantages of short route, high reaction yield in each step, simple operation and convenience in mass production.

Efficient synthesis of (5Z,7E)-Dodecadienal, the sex pheromone of the european pine moth dendrolimus pini

Efficient synthesis of (5Z,7E)-dodecadienal, the sex pheromone of European pine moth Dendrolimus pini, was stereoselectively accomplished via Pd- and Fe- catalyzed cross-coupling reactions in the key steps. The very simple and practical method developed herein provides a general synthetic approach to other (Z,E)-diene compounds.

Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, lepidoptera pheromone components, via zinc reduction of enyne precursors. Test of pheromone efficacy against the Siberian moth

Efficient syntheses of (Z,E)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semihydrogenation was ≥98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80 °C were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.

Insertion of 1-chloro-1-lithioalkenes into organozirconocenes. A versatile synthesis of stereodefined unsaturated systems

Hydrozirconation of alkenes and alkynes, followed by insertion of 1- halo-1-lithio-1-alkenes, generated in situ by lithium tetramethylpiperidide deprotonation of vinyl halides, affords vinylzirconocene species which may be further elaborated. The method provides easy access to many structures including terminal (3E)- and (3Z)-1,3-dienes and (3E,5E)- and (3Z,5E)-1,3,5- trienes, and internal (E,Z)-dienes,(E,Z,E)-trienes, and (1E, 3Z)1,3-dien-5- ynes. Insertion of 2-monosubstituted 1-halo-1-lithio-1-alkenes occurs with clean inversion of configuration of the sp2-carbenoid carbon. Carbenoids derived by deprotonation of 2,2-disubstituted 1-halo-1-alkenes gave poor stereocontrol probably due to isomerization before insertion into the organozirconium species. Insertion of vinyl carbenoids into alkynylzirconocenes affords terminal (3E)- or (3Z)-1,3-dien-5-ynes, internal (1E,3Z)-1,3-dien-5-ynes, and (Z)-3-en-1,5-diynes.

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.

Oxidation of Alcohols with Electrolytic Manganese Dioxide. Its Application for the Synthesis of Insect Pheromones

Oxidation of alcohols with electrolytic manganese dioxide under mild conditions afforded aldehydes and ketones in good yields.The method was applied for the syntheses of cystophorene (15) and a sex pheromone of forest tent cater pillar .

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.