57981-60-9

Basic information

• Product Name: (Z,E)-trideca-4,7-dien-1-yl acetate
• Synonyms: (Z,E)-trideca-4,7-dien-1-yl acetate;(E,Z)-4,7-Tridecadienyl acetate;Einecs 261-058-2;(4E,7Z)-deca-4,7-dienyl acetate;4,7-Tridecadien-1-ol,1-acetate, (4E,7Z)-;4E7Z-13Ac
• CAS NO: 57981-60-9
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.36574
• EINECS: 261-058-2
• Mol File: 57981-60-9.mol

Chemical Properties

• Boiling Point: 302.2°Cat760mmHg
• Flash Point: 91°C
• Appearance: /
• Density: 0.893g/cm³
• Vapor Pressure: 0.00101mmHg at 25°C
• Refractive Index: 1.462
• CAS DataBase Reference: (Z,E)-trideca-4,7-dien-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,E)-trideca-4,7-dien-1-yl acetate(57981-60-9)
• EPA Substance Registry System: (Z,E)-trideca-4,7-dien-1-yl acetate(57981-60-9)

Safety Data

• Hazardous Substances Data: 57981-60-9(Hazardous Substances Data)

Usage

Uses

Used in Pest Control:
(Z,E)-trideca-4,7-dien-1-yl acetate is used as a pheromone in pest control for the potato tuber moth. (Z,E)-trideca-4,7-dien-1-yl acetate acts as a chemical attractant, luring the male moths towards the source of the pheromone, which can then be captured or monitored. This application helps in managing and controlling the population of the potato tuber moth, a significant agricultural pest that causes damage to potato crops.
Used in Chemical Synthesis:
(Z,E)-trideca-4,7-dien-1-yl acetate can also be used as a synthetic intermediate in the production of various chemicals and compounds. Its unique structure with the conjugated diene system and acetate functional group makes it a valuable building block for the synthesis of complex organic molecules, potentially leading to new materials and applications in various industries.
Used in Research and Development:
(Z,E)-trideca-4,7-dien-1-yl acetate (Z,E)-trideca-4,7-dien-1-yl acetate is utilized in research and development for studying the behavior and biology of the potato tuber moth and other related species. Understanding the chemical communication and mating patterns of these insects can provide valuable insights into their ecology and help develop more effective pest management strategies.

InChI:InChI=1/C15H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-17-15(2)16/h7-8,10-11H,3-6,9,12-14H2,1-2H3

Upstream product

• 68236-05-5 ethyl 4(E),7(Z)-tridecadienoate 
• 75-36-5 acetyl chloride 
• 57981-61-0 (4E,7Z)-4,7-Tridecadien-1-ol 
• 108-24-7 acetic anhydride 
• 84565-15-1 (4E,7Z)-4,7-tridecadienoic acid 
• 89473-49-4 (4E,7Z)-Trideca-4,7-dienenitrile 
• 5390-04-5 pent-1-yn-5-ol 
• 25466-54-0 (Z)-1-bromo-2-octene 
• 107691-98-5 (Z)-7-tridecen-4-yn-1-ol 
• 6089-09-4 4-pentynoic acid 
• 168422-42-2 7Z-tridec-7-en-4-yn-1-oic acid 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 26001-58-1 (Z)-oct-2-en-1-ol 
• 5910-87-2 (E,E)-2,4-nonadienal 

Relevant articles and documents

A simple synthesis of 4E,7Z-tridecadien-1-yl acetate, a component of the sex pheromone of the potato moth Phtorimaea operculella (Lepidoptera: Gelehiidae)

A simple, five-step synthesis of the title compound was developed starting from commercially available 2,4-nonadienal. The overall yield of the pheromone is 29%, and the geometric purity of the Δ4 and Δ7 double bonds is ≥95%. The Z configuration of the Δ7 bond results from the 1,4-cis-hydrogenation of the intermediate 1,4,6-undecatrien-3-ol in the presence of an (arene)chromium tricarbonyl complex, while the E configuration of the Δ4 bond arises in the Claisen-Johnson rearrangement occuring in the reaction of 1,5Z-undecadien-3-ol with trimethyl orthoacetate.

Exo- and endohormones XXI 1: Stereoselective synthesis of the four isomers of the 4,7-tridecadien-1-yl acetate. (4E,7Z)-4,7-tridecadien-1-yl acetate, the sex pheromone of the leafminer moth Phylonorycter corylifoliella

The synthesis of the four isomers of 4,7-tridecadien-1-yl acetate, based on a C5+C8 scheme is described. The coupling reaction took place between the Grignard reagent of pent-4-yn-1-oic acid and 1-bromo-2(Z/E)-octene. The four isomers were separated on SiO2-AgNO3 TLC plate and GS-MS. (4E,7Z)-4,7-Tridecadien-1-yl acetate is the sex pheromone of the spottet tentiform leafminer moth Phylonorycter corylifoliella.

Insect pheromones and their analogs LV. Synthesis of trideca-4E,7Z-dien-1-yl acetate - Component of the sex pheromone of Phthorimaea opercucella

Starting from propargyl alcohol and using the thermal Claisen rearrangement at the stage of constructing the (E)-double bond, we have synthesized trideca-4E, 7Z-dien-1-yl acetate - a component of the sex pheromone of the potato moth Phthorimaea opercucella (Zeller).

EXO- AND ENDOHORMONES, XVI SYNTHESIS OF (4E, 7Z)-4,7-TRIDECADIEN 1-YL ACETATE, THE SEX PHEROMONE FOR THE LEAFMINER LITHOCOLLETIS CORYLIFOLIELLA

The synthesis of the sex pheromone of the leafminer moth, Lithocolletis corylifoliella, (4E, 7Z)-4,7-tridecadien-1-yl acetate, was based on a C5+C8 scheme.The coupling reaction took place between the Grignard reagent of 4-pentin-1-1-oic acid and 1-bromo-2Z-octene.Propargylic alcohol was used as a starting material in order to obtain the two synthons.

Stereoselective Synthesis of 1,4-Dienes. Application to the Preparation of Insect Pheromones (3Z,6Z)-Dodeca-3,6-dien-1-ol and (4E,7Z)-Trideca-4,7-dienyl Acetate

Stereoselective synthesis of Z,E- and Z,Z-1,4-dienes has been achieved by the cross-coupling of allylic substrates with vinyl organometallic reagents.Key to this strategy was the development of a method for regiospecific incorporation of a tri-n-butylstannyl group in the γ-position of the allylic cross-coupling partner.The steric bulk of this moiety ensures the stereochemical integrity of the allylic double bond throughout the coupling sequence and is easily replaced by hydrogen in the coupled product.This strategy has been applied to the synthesis of the termite trail marker pheromone 22 and the leafminer moth sex pheromone 28.

ALKYLATION OF ACETYLCYCLOPROPANE CYCLOHEXYLIMINE BY ETHYLENE OXIDE DERIVATIVES AS A KEY STEP IN THE SYNTHESIS OF SOME INSECT ACETOGENIN PHEROMONES

The interaction of Li derivatives of acetylcyclopropane cyclohexylimine with ethylene, propylene, and isoprene oxides leads efficiently to the corresponding γ-cyclopropylketols.The cyclopropylcarbinol corresponding to the first of them is smoothly converted under the action of the couple Me3SiBr/ZnBr2 to a linear E-C7-homoallyl bromide, which is then used in the stereocontrolled synthesis of tridec-4E-enyl and trideca-4E,7Z-dienyl acetates - components of the sex pheromones of some Lepidoptera species.Keywords: acetylcyclopropane, insect acetogenin pheromones, homoallyl rearrangement, Julia olefination, olefin oxides.

Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones

Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.

Organoaluiminum-promoted claisen rearrangement of allyl vinyl ethers

Unprecedentad stereochemical control has achieved in the Claisen of allyl vinyl of type 4 with certain bulky organoaluminum Thus, methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (reagent A) can be utilized for obtaining the (Z) isomer, (Z)-6, whereas the (E) isomer, (E)-6 was produced with methylaluminum bis(2,6-diphenylphenoxide) (reagent B). This organoaluminum-promoted Claisen rearrangement proceeds under very mild conditions with very good E and Z selectlvities. On the basis of the Claisen rearrangement of optically active substrate 7 with reagent A, the Z selectivity would be interpreted by the intervention of the chairlike transition-state conformation with the isobutyl substituent axial. The present organoalunminum-promoted Claisen rearrangement has successfully applied to the synthesis of (4E,7Z)-4,7-tridecadienyl acetate (15), a component of the sex of tuberworm moth, in stereoselective fashion. Furthermore, the Claisen rearrangement of bisallyl vinyi ether16 with reagent A or B has been found to involve the more substituted allylic system to furnish dienal 18 preferentially, not obtainable in the ordinary thermal rearrangement. This chemistry been further extended to the ionic rearrangement of dienyl vinyl ether 28 by using reagent A in a polar solvent the previously unknown, remote transfer of the vinyloxy moiety by [3,5]-sigmatropic rearrangement via ionic intermediate 29 has observed.

SYNTHETIC INVESTIGATIONS IN THE FIELD OF INSECT ATTRACTANTS (SEX ATTRACTANTS). II. SYNTHESIS OF FOUR ISOMERS OF 4,7-TRIDECADIENYL ACETATE AND (E,Z,Z)-4,7,10-TRIDECATRIENYL ACETATE

A common approach was developed to the synthesis of (E,Z)-4,7-tridecadienyl and (E,Z,Z)-4,7,10-tridecatrienyl acetates, which are the main components of the sex pheromone of the female potato moth Phtorimaea operculella, on the basis of 4-pentyn-1-ol and allyl halides.The Z,Z, Z,E, and E,E isomers of 4,7-tridecadienyl acetate were also obtained by the method.