71720-83-7

Usage

Uses

Used in Insect Pest Management:
(11Z,13Z)-11,13-Hexadecadien-1-ol is used as a mating disruptant for controlling insect populations, particularly in the case of moths from the genus Spodoptera. It disrupts insect mating behaviors, thereby helping to manage pest populations.
Used in Fragrance Production:
(11Z,13Z)-11,13-Hexadecadien-1-ol is used as a component in the production of fragrances due to its natural occurrence in pheromones and insect attractants, contributing to the creation of unique and complex scents.
Used as a Chemical Intermediate:
(11Z,13Z)-11,13-Hexadecadien-1-ol may also be used as a chemical intermediate for the synthesis of other compounds in various industrial applications, given its unique chemical structure and properties.

InChI:InChI=1/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h3-6,17H,2,7-16H2,1H3/b4-3+,6-5+

Upstream product

• 71685-56-8 (Z,Z)-1-(2-Tetrahydropyranyloxy)-11,13-hexadiene 
• 85920-81-6 10-bromodecanal 
• 79239-47-7 1,1-diethoxy-10-bromodecanal 
• 98498-54-5 10-iododecanal diethyl acetal 
• 53463-68-6 1-bromo-10-decanol 
• 1214742-94-5 (Z)-1,1-diethoxyhexadec-13-en-11-yne 
• 71317-73-2 (11Z,13Z)-11,13-hexadecadienal 
• 152488-40-9 1-(2-tetrahydropyranyloxy)-2-dodecyne 
• 71084-07-6 1-tetrahydropyranyloxy 11-dodecyne 
• 18202-10-3 11-dodecyn-1-ol 
• 693-58-3 1-Bromononane 
• 69064-46-6 dodec-2-yn-1-ol 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 71673-33-1 2-Hexadeca-11,13-diynyloxy-tetrahydro-pyran 

Downstream Products

• 71317-73-2 (11Z,13Z)-11,13-hexadecadienal 
• 73264-89-8 (Z₁₁,E₁₃)-11,13-Hexadecadienal 
• 73264-90-1 (11E,13Z)-hexadeca-11,13-dienal 
• 73264-91-2 (11E,13E)-11,13-hexadecadienal 

Relevant academic research and scientific papers

Facile and efficient syntheses of (11Z,13Z)-hexadecadienal and its derivatives: Key sex pheromone and attractant components of notodontidae

Syntheses of (11Z,13Z)-hexadecadienal (1), (11Z,13Z)-hexadecadienol (2), (11Z,13Z)-hexadecadien-1-yl acetate (3), and (Z)-13-hexadecen-11-ynal (4) from commercially available starting material 10-bromo-1-decanol are reported. These (Z,Z)-dienes and conjugated en-yne moieties are common in sex pheromone and attractant components for many Notodontide insect pests. The synthetic scheme, using the C10 + C3 + C3 strategy, was mainly based on three key steps: Alkylation of lithium alkyne under a low temperature, cis-Wittig olefination of the aldehyde with propylidentriphenylphosphorane, and hydroboration-protonolysis of alkyne. This synthetic route provided (11Z,13Z)-hexadecadienal (1) in a 23.0% total yield via an eight-step sequence, alcohol (2) in a 21.9% total yield, acetate (3) in a 21.4% total yield, and (Z)-13-hexadecen-11-ynal (4) in a 34.7% total yield. This simple strategy provides a new way to achieve syntheses of the key sex pheromones of Notodontide insect pests.

Synthetic pheromone compositions

The present invention provides compounds useful for preparing synthetic pheromone compositions that can be used as attractants or inhibitors of insect species. The compositions are useful in the control of navel orangeworm or meal moth insect pests.

ALKENYL COPPER REAGENTS-26 CARBOCUPRATION OF ALKYNES BY ORGANOCOPPER REAGENTS BEARING A PROTECTED HYDROXY OR THIOL FUNCTION

Halohydrins, protected as ethers, acetals or chloro-magnesium alcoholates are sequentially transformed into the Li or Mg reagents and then into copper or cuprate derivatives.Addition to acetylene or propyne is discussed according to various parameters.The alkenyl copper or cuprate species, thus obtained, may react further with various electrophiles, leading to difunctionalized alkenes.

GENERAL METHODOLOGY FOR THE SYNTHESIS OF CONJUGATED DIENIC INSECT SEX PHEROMONES

A general methodology for the synthesis of various type of dienic insect sex pheromones (Z-E, E-Z, Z-Z) is based on the carbocupration of acetylene by functionalised or non-functionalised lithium dialkyl cuprates, followed by the coupling of the resulting Z dialkenyl cuprates with functionalised or non-functionalised E or Z alkenyl iodides under Pd0 catalysis.The following compounds were efficiently synthesized with a high degree of stereoisomeric purity: (E-Z)7,9-dodecadien,-1-yl acetate 1 (Lobesia botrana), (E-Z)10,12-hexadecadien,-1-ol 2 (Bombyx mori), (Z-E)9,11-tetradecadien,-1-yl acetate 3 (Spodoptera littoralis), (Z-E)5,7 dodecadien-1-ol 4 (Malascoma disstria), (Z-Z)11, 13-Hexadecadien-1-al 5 (Amyelois transitella), (Z)9,11-dodecadien-1-yl acetate 6 (Diparopsis castanea) and (Z-Z)9,11-tridecadien-1-yl acetate 22 (a known "pseudo-pheromone").

(11Z,13Z)-11,13-Hexadecadien-1-ol and derivatives

Synthesis of an attractant (11Z,13Z)-11,13-hexadecadienal for the navel orangeworm Amyelois transitella, and intermediates therefor.

(11Z,13Z)-11,13-Hexadecadiyn-1-ol and (11Z,13Z)-11,13-hexadecadien-1-ol and trimethylsilyl ethers thereof

Synthesis of an attractant (11Z,13Z)-11,13-hexadecadienal for the navel orangeworm Amyelois transitella, and intermediates therefor.