28540-79-6

Usage

Uses

Used in Fragrance Industry:
(E)-tetradec-7-enyl acetate is used as a fragrance ingredient for its sweet, fruity scent. It is commonly utilized in the production of perfumes, soaps, and other fragrances to provide a pleasant and attractive aroma.
Used in Agricultural Industry:
(E)-tetradec-7-enyl acetate is used as a potential insecticide for its activity against certain insect pests. It has been studied for its insecticidal properties, which could be beneficial in controlling and managing insect populations that may be harmful to crops or the environment.

InChI:InChI=1/C16H30O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h8-9H,3-7,10-15H2,1-2H3/b9-8+

Upstream product

• 37011-95-3 (7E)-tetradec-7-en-1-ol 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 2009-84-9 (chloro-6' hexyloxy)-2 tetrahydropyranne 
• 38761-67-0 1-bromo-1-octyne 
• 55305-38-9 (E)-2-(tetradec-7-en-1-yloxy)tetrahydro-2H-pyran 
• 56318-83-3 (E)-1-bromo-oct-2-ene 
• 18409-17-1 (E)-oct-2-en-1-ol 
• 7367-81-9 methyl (E)-oct-2-enoate 
• 73881-09-1 (E)-2-octenylphosphonic acid diethyl ester 
• 83748-47-4 (E)-1,6-tridecadiene 
• 693-25-4 n-pentylmagnesium bromide 
• 15972-89-1 (E)-1-phenoxy-2,7-octadiene 
• 83748-49-6 1-bromo-6E-tridecene 

Relevant academic research and scientific papers

Pheromones via Organoboranes. 3. Vinylic Organoboranes. 10. Stereospecific Synthesis of (Z)- and (E)-6- and -7-Alken-1-ols via Boracyclanes

Treatment of B-(E)-1-alkenylborinanes, obtained via monohydroboration of 1-alkynes with borinane, with iodine in the presence of a base results in the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, producing intermediates containing the seven-membered borepane moiety, which undergo rapid deiodoboronation to afford the (Z)-6-alkenyl-1-boronate esters.These boronate esters, upon oxidation, provide (Z)-6-alken-1-ols.The procedure is successfully extended to B-(E)-7-alkenylborepane derivatives to produce (Z)-7-alken-1-ols.The preparationof (E)-6- and -7-alken-1-ols has been carried out via borinane and borepane derivatives.Borinane, as prepared previously, hydroborates cleanly 1-bromo-1-alkynes to provide the B-((Z)-1-bromo-1-alkenyl)borinanes.Treatment of these boron intermediates with sodium methoxide results in the displacement of bromine by one end of the boracycloalkyl moiety, producing the corresponding vinylboranes containing the seven-membered borepane moiety.The intermediates, upon controlled protonolysis, followed by oxidation, afford the (E)-6-alken-1-ols.The methodology was extended to borepane derivatives to provide (E)-7-alken-1-ols.The above procedures constitute a simple, very convenient, stereospecific, and general one-pot synthesis of (Z)- and (E)-6- and -7-alken-1-ols.The methodology has been applied to the synthesis of representative pheromones containing a (Z)- or an (E)-alkene moiety in good yields.

PHEROMONE SYNTHESIS VIA ORGANOBORANES: A STEREOSPECIFIC SYNTHESIS OF (E)-7-ALKEN-1-OLS

Borepane, obtained via hydridation of B-chloroborepane, hydroborates 1-bromo-1-alkynes cleanly to provide the B-(cis-1-bromo-1-alkenyl)borepanes.Treatment of these intermediates with sodium methoxide results in the displacement of bromine by one end of the boracycloalkyl moiety, producing the corresponding vinylboranes, containing the eight-membered borocane moiety.These intermediates, on controlled protonolysis followed by oxidation, provide the (E)-7-alken-1-ols.This process constitutes a simple, very convenient, stereospecific and general one-pot synthesis of (E)-7-alken-1-ols.Pheromones, (E)-7-tetradecen-1-ol, (E)-7-tetradecen-1-ol acetate and (E)-7-dodecen-1-ol acetate were prepared in excellent yields.

STEREOSPECIFIC SYNTHESIS OF PHEROMONES OF THE E-ALKENE SERIES FROM THE TELOMER OF BUTADIENE WITH PHENOL

The stereospecific synthesis of 7E- and 9E-dodecenyl acetates, 7E- and 11E-tetradecenyl acetates, 11E-tetradecen-1-ol, and 11E-hexadecenyl acetate, i.e., E-olefinic sex pheromones, was realized from 1-phenoxy-2E,7-octadiene (the telomer of butadiene with phenol).

INSECT SEX PHEROMONES. STEREOSELECTIVE SYNTHESIS OF SEVERAL (Z)- AND (E)-ALKEN-1-OLS, THEIR ACETATES, AND OF (9Z,12E)-9,12-TETRADECADIEN-1-YL ACETATE

Several female sex pheromone components produced by moths belonging to the order of Lepidoptera, and potential attractants of Dacus oleae (Diptera:Tripetidae) have been synthesized in high chemical and stereoisomeric purity by improved acetylenic routes involving alkylation of lithium 1-alkyn-1-ides in HMPT, followed by (Z) and (E) highly stereoselective reduction of the derived internal alkynes.Particular care has been paid to optimize the parameters of the reactions used and to evaluate the chemical and isomeric purity of the reaction products.The compounds synthesized include (Z)- and (E)-5-nonen-1-ol, (Z)- and (E)-7-dodecen-1-yl acetate, (Z)- and (E)-7-teradecen-1-yl acetate, (Z)- and (E)-7-nonen-1-ol, (Z)- and (E)-9-tetradecen-1-yl acetate, (Z)- and (E)-10-tetradecen-1-yl acetate, (Z)- and (E)-11-tetradecen-1-yl acetate.Pure (Z)-6-nonen-1-ol, which is an attractant of olive fruit fly, D. oleae, and very probably, a constituent of the sex pheromone of females of this insect, has been prepared by a rather efficient copper-catalyzed reaction between (Z)-3-hexen-1-ylmagnesium bromide and oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate, which is the pheromone of Anagasta kuenniella, Ephestia elutella, Cadra figulella, Spodoptera exigua, S. litura, and a component of the sex pheromones of several other Lepidoptera, has been conveniently prepared by using the copper-catalyzed coupling reaction between (E)-1-chloro-2-butene and 10-tetrahydropyranyloxy-1-decenylmagnesium bromide, followed by acetylation and Z-stereoselective reduction of the derived 1,4-enyne.All syntheses have been conducted on a scale to yield less than 50 mmol of the pure sex pheromone components, but seem adaptable for much larger quantities.