78617-58-0

Basic information

• Product Name: Acetic acid (Z)-13-hexadecene-11-yne-1-yl ester
• Synonyms: (Z)-13-Hexadecen-11-yn-1-ol acetate;(Z)-13-Hexadecene-11-yne-1-ol acetate;Acetic acid (13Z)-13-hexadecene-11-ynyl ester;Acetic acid (Z)-13-hexadecene-11-yne-1-yl ester;Acetic acid (Z)-13-hexadecene-11-ynyl ester;(Z)-13-hexadecen-11-ynyl acetate
• CAS NO: 78617-58-0
• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.4296
• Mol File: 78617-58-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acetic acid (Z)-13-hexadecene-11-yne-1-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (Z)-13-hexadecene-11-yne-1-yl ester(78617-58-0)
• EPA Substance Registry System: Acetic acid (Z)-13-hexadecene-11-yne-1-yl ester(78617-58-0)

Safety Data

• Hazardous Substances Data: 78617-58-0(Hazardous Substances Data)

Usage

Uses

(Z)-13-Hexadecen-11-ynyl Acetate is a sex pheromone of pine processionary moth.

Upstream product

• 53596-78-4 11-dodecyn-1-yl acetate 
• 54068-75-6 (Z)-1-iodobut-1-ene 
• 108-24-7 acetic anhydride 
• 75089-05-3 (Z)-13-Hexadecen-11-ynyl alcohol 
• 75-36-5 acetyl chloride 
• 31844-98-1 (E)/(Z)-1-bromo-1-butene 
• 18202-10-3 11-dodecyn-1-ol 
• 88109-70-0 n-5-dodecyn-1-ol 
• 17894-04-1 1-tetrahydropyranyloxy-n-5-dodecyn 
• 75089-04-2 tetrahydropyranyl ether of (13Z)-13-hexadecen-11-yn-1-ol 
• 1002-77-3 12-chloro-1-dodecyne 
• 127-09-3 sodium acetate 

Downstream Products

• 629-70-9 hexadecyl acetate 
• 107996-38-3 13-fluoro-14-tosylhexadec-11-ynyl acetate 
• 107996-38-3 13-fluoro-14-tosylhexadec-11-ynyl acetate 
• 78648-85-8 14-hydroxyhexadecyl acetate 

Relevant articles and documents

Omega-halo-2-alkynal, method for producing same, and method for producing conjugated Z-alken-yn-yl acetate using same

Provided is a method for industrially producing a conjugated Z-alken-yn-yl acetate such as Z-13-hexadecen-11-yn-yl acetate which is a sex pheromone component of a pine processionary moth, and an intermediate for the conjugated Z-alken-yn-yl acetate under mild conditions at a high yield. More specifically, provided is a method for producing a conjugated Z-alken-yn-yl acetate (5) comprising the steps of: reacting an ω-halo-2-alkynal (1) with an alkylidene triphenylphosphorane (3) through a Wittig reaction to obtain a conjugated Z-alken-yn-yl halide (4), and acetoxylating the conjugated Z-alken-yn-yl halide (4) into a conjugated Z-alken-yn-yl acetate (5).

Une synthese courte et stereoselective de l'Acetoxy-1 hexadecane-13 (Z)yne-11 : Principal constituant de la secretion pheromonale produite par la femelle vierge de la Processionnaire du pin Theumetopoes pityocampa (Danis et Schiff.) (Lepidoptera notodontides).

Resume : Une synthese courte et stereoselective de la pheromone sexuelle de la Processionnaire du pin : Thaumatopoes pityocamps (Denis et Schiff.) a ete realisee.Cette synthese utilise dans son etape finale une reaction de couplage d'un acetate ω-acetylenique sur un halogenure vinylique dans le benzene en presence de quantites catalytiques de tetrakis(triphenylphosphine)palladium et d'iodure cuivreux.

SYNTHESIS OF THE TWO ISOMERS OF THE POTENTIAL SEX PHEROMONE OF THAUMETOPOEA PITYOCAMPA (LEPIDOPTERA, NOTODONTIDAE) AND RELATED MODEL COMPOUNDS

The synthesis of the major component of the sex pheromone secretion of the processionary moth, Thaumetopoea pityocampa (Denis and Schiff.) (Lepidoptera, Notodontidae), (Z)-13-hexadecen-11-ynyl acetate (1), the corresponding (E)-isomer (2) and the four structurally related model compounds (Z/E,Z,Z)-5,9,13-hexadecatrienyl acetate (3), (Z/E,Z,Z)-3,7,11-hexadecatrienyl acetate (4), (Z/E,E,Z)-7,9,13-hexadecatrienyl acetate (5) and (Z)-7-hexadecen-5-ynyl acetate (6) is described.