78617-58-0

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

Downstream Products

• 78648-85-8 14-hydroxyhexadecyl acetate 
• 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 

Relevant academic research and scientific papers

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).

STEREOSPECIFIC SYNTHESIS OF (Z)-13-HEXADECEN-11-YN-1-YL ACETATE THE SEX PHEROMONE OF THE PROCESSIONARY MOTH, AND OF (5Z,7E)-5,7-DODECADIEN-1-OL, A SEX PHEROMONE COMPONENT OF THE FOREST TENT CATERPILLAR

(Z)-13-hexadecen-11-yn-1-yl acetate (2), the sex pheromone of Thaumetopoea pytyocampa, and (5Z,7E)-5,7-dodecadien-1-ol (3), sex pheromone component of Malacosoma disstria, have been prepared in high chemical and stereoisomeric purity by synthetic schemes involving the stereospecific coupling of ω-functionalized 1-alkynes with (Z)- or (E)-1-iodo-1-alkenes in the presence of a catalytic amount of (PPh3)4Pd and CuI, under phase transfer conditions.

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.

A STEREOSELECTIVE SYNTHESIS OF (Z)-13-HEXADECEN-11-YNYL ACETATE, THE SEX PHEROMONE OF Thaumetopoea pityocampa (LEPIDOPTERA, NOTODONTIDAE)

(Z)-13-Hexadecen-11-ynyl acetate, 1, the sex pheromone of Thaumetopoea pityocampa, has been synthesized stereospecifically, starting from anion of 3--1-hexyne, 8, which was alkylated with 10-iodo-1-decane; the intermediate diol 2, obtained upon removal of the protecting groups was stereoselectively dehydrated with KHSO4.

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.