57981-61-0

Usage

Uses

Used in Perfumery Industry:
(Z,E)-trideca-4,7-dien-1-ol is used as a fragrance ingredient for its pleasant odor, contributing to the creation of various perfumes and scented products.
Used in Flavor Industry:
It is utilized as a flavoring agent for its agreeable taste, enhancing the flavor profiles of food and beverage products.
Used in Pharmaceutical Industry:
(Z,E)-trideca-4,7-dien-1-ol is used as a bioactive compound for its potential medicinal properties, which may include therapeutic applications based on its biological activities.
Used in Cosmetic Industry:
It serves as an ingredient in cosmetic products, leveraging its properties to improve product efficacy and performance, such as in skincare and haircare formulations.

InChI:InChI=1/C13H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h6-7,9-10,14H,2-5,8,11-13H2,1H3/b7-6+,10-9-

Upstream product

• 33821-94-2 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide 
• 132124-56-2 (1E,4Z)-1-Bromo-deca-1,4-diene 
• 124381-46-0 (4E,7Z)-4,7-tridecadienal 
• 107691-98-5 (Z)-7-tridecen-4-yn-1-ol 
• 139269-70-8 (4E,7Z)-1-(tetrahydropyran-2-yloxy)trideca-4,7-diene 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 111-12-6 methyl 2-octynoate 
• 72538-17-1 undec-1-en-5-yn-3-ol 
• 111285-93-9 ethyl (4E)-tridecen-7-ynoate 
• 628-71-7 1-Heptyne 
• 89682-47-3 (3Z)-3-nonenal diethyl acetal 
• 90290-02-1 3-nonynal diethyl acetal 
• 31823-43-5 (Z)-3-nonenal 
• 1573-66-6 hex-1-en-5-yn-3-ol 

Downstream Products

• 57981-60-9 (4E,7Z)-4,7-tridecadien-1-yl acetate 
• 68236-06-6 (4Z,7Z)-4,7-Tridecadien-1-yl acetate 

Relevant academic research and scientific papers

Nonconjugated Dienes from 1-Alkenes: Application to the Synthesis of Sex Pheromone (4E,7Z)-4,7-Tridecadienyl Acetate

(4E,7Z)-4,7-Tridecadienyl acetate 1, a component of the sex pheromone was synthesized from 5-hexenyl acetate. (E)-γ,δ-Unsaturated phosphonate as the key intermediate afforded a target molecule, using the Horner-Wadsworth-Emmons (HWE) reaction and desulfonylation as the main process.

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).

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.

Mammalian Exocrine Secretions: IX. Constituents of Preorbital Secretion of Oribi, Ourebia ourebi

Using gas chromatography-mass spectrometry in conjunction with ancillary techniques such as chemical ionization with different reactant gases, determination of the position of double bonds by means of dimethyl disulfide derivatization, and finally gas chromatographic and mass spectrometric comparison with authentic synthetic material, 75 constituents were identified in the preorbital secretion of the male oribi, Ourebia ourebi. The secretion contains compounds with long-chain, unbranched structures similar to those found in many other preorbital secretions but with a finite volatility range, in contrast to the seemingly endlessly increasing chain lengths typical of other preorbital secretions.

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.