38363-29-0

Usage

Uses

(8E)-Dodecenyl Acetate functions as pheromone of green budworm moth.

InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h5-6H,3-4,7-13H2,1-2H3/b6-5+

Upstream product

• 42513-42-8 E₈,E₁₀-dodecadien-1-ol 
• 75-36-5 acetyl chloride 
• 153123-34-3 Δ⁸-dodecen-1-ol 
• 108-24-7 acetic anhydride 
• 1779-51-7 n-butyl(triphenyl)phosphonium bromide 
• 821-57-8 7-chloroheptanoic acid 
• 41589-71-3 8-Dodecyn-1-ol 
• 18545-07-8 8-Dodecinsaeure 
• 817210-79-0 Z/E-8-dodecenyl bromide 
• 127-09-3 sodium acetate 
• 77328-78-0 (8-Acetoxyoctyl)-triphenylphosphonium-bromid 
• 123-72-8 butyraldehyde 
• 81744-94-7 7-tetrahydropyranyloxy-heptyl-magnesium chloride 
• 64604-68-8 1-(2-tetrahydropyranyloxy)dodec-8-ene 

Downstream Products

• 28079-04-1 (Z)-8-dodecen-1-yl acetate 

Relevant academic research and scientific papers

Identification, synthesis, and field evaluation of the sex pheromone of the citrus fruit borer: Ecdytolopha aurantiana

The sex pheromone of the citrus fruit borer Ecdytolopha aurantiana has been identified by gas chromatography coupled to an electroantennographic detector (GC-EAD). The electron impact mass spectral (EI-MS) fragmentation of the major EAD-active peak gave identifying features for a monounsaturated acetate. Further analyses by chemical ionization mass spectrometry (CI-MS), vapor-phase infrared spectroscopy (GC-IR), along with chemical derivatization (DMDS reaction), led to full characterization of the major component as (E)-8-dodecenyl acetate (E8-12:Ac). The second constituent was identified as the related alcohol, (E)-8-dodecenol (E8-12: OH). The two compounds were indistinguishable from the authentic synthetic standards in chemical and EAD analyses. Samples of the two compounds were obtained by a facile synthesis utilizing lithium chemistry. Field tests showed that captures in traps baited with a mixture of E8-12: Ac and E8-12: OH at 100:1 and 10:1 ratios were not significantly different from the catches in traps having two virgin females. Dosage tests showed better performance of traps baited with 1 mg than those with 0.1 mg of the pheromone blend, either in 100:1 or 10:1 ratio.

Synthesis method of (Z/E)-8-dodecen-1-alcohol acetate compound

The invention provides a synthesis method of a (Z/E)-8-dodecane-1-alcohol acetate compound. Specifically, the method includes the following steps: preparing 8-bromooctanol from 1,8-octanediol, then performing esterification reaction to obtain 8-Bromooctanol acetate, and then preparing omega-acetoxyoctanyl triphenyl phosphine bromide salt, and finally performing reaction through Scholoer-wittig toobtain (Z/E)-8-dodecene-1-alcohol acetate. The synthesis method has the advantages of high availability of raw materials, high yield and good selectivity, and is suitable for industrial production.

A (Z/E) - 8 - dodecene -1 - ethoxylate ester synthesis method

The invention discloses a (Z/E)-8-dodecylene-1-olacetate synthesis method. The method is characterized in that 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials undergo a coupling reaction to produce 8-(2-oxotetrahydropyranyl)dodecyne, the 8-(2-oxotetrahydropyranyl)dodecyne is subjected to hydrogenation, one-pot deprotection and esterification so that (Z)-8-dodecylene-1-olacetate and (E)-8-dodecylene-1-olacetate are obtained, wherein a mole ratio of (Z)-8-dodecylene-1-olacetate to (E)-8-dodecylene-1-olacetate is (90%-99.5%): (10%-0.5%). The method utilizes 1-halogenated pentine and magnesium 1-(2-oxotetrahydropyranyl)heptylhalide as initial raw materials, provides a novel reaction route, has a short route, produces less by-product, has simple and routine processes, is free of complex post-reaction treatment processes and improves production efficiency. The method satisfies different insect pheromone trap or lure requirements on an isomer ratio in practical application and is suitable for large-scale industrial production.

A pheromone food heart insectthe pear is small (Z/E)-8-dodecene acetum acid ester synthetic method

The invention provides a synthesis method of grapholitha molesta sex pheromone (Z/E)-8-dodecene acetate. The synthesis method comprises the following steps: (1) by taking methylbenzene or benzene as a solvent and 1,8-octanediol and hydrobromic acid as starting raw materials, performing unilateral bromination reaction to obtain 8-bromooctanol; (2) by taking ethanol as a solvent, adding 8-bromooctanol and triphenylphosphine into a reaction kettle, after the reaction, cooling and separating out 8-hydroxyl octyl triphenylphosphine crystals by taking methylbenzene as an eluent; (3) performing Witting reaction on the 8-hydroxyl octyl triphenylphosphine and n-butyraldehyde under the presence of a catalyst 18-crown ether-6 to obtain (Z/E)-8-dodeceneanol, wherein potassium carbonate is adopted as alkali; and (4) by taking pyridine as a solvent, reacting the (Z/E)-8-dodeceneanol with acetic anhydride or acetyl chloride to obtain (Z/E)-8-dodecene acetate. The method mild in conditions, fewer in steps, high in yield, and suitable for industrial production, and raw materials are easily available.

SYNTHESIS OF Z-OLEFIN-CONTAINING LEPIDOPTERAN INSECT PHEROMONES

The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

Novel convenient synthesis of (Z/E)-8-dodecenyl acetates, components of the Grapholitha molesta sex pheromone

Components of the Grapholitha molesta sex pheromone, (Z/E)-8-dodecenyl acetates (1, 2), were synthesized in five steps in 20% overall yield using 10-hydroxydecanoic acid (3) as starting material.

Process for preparing functional group-containing olefinic compounds

A process for preparing functional group-containing olefinic compounds comprises the steps of (a) reacting at least one alkylidene phosphorane with at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, to form an olefinic compound that comprises at least one leaving group, the carbonyl-containing compound being selected from the group consisting of ketones and aldehydes; and (b) reacting the olefinic compound with at least one functional group-containing nucleophile to form a functional group-containing olefinic compound.

Use of enyne compounds in the synthesis of insect pheromones

A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.

Method for the isomerization of cis-alkenyl compounds

An object of the present invention is to provide a method for the preparation of geometrical isomers which are important as constituents of synthetic pheromones, synthetic perfumes, terpenes and the like (i.e., a method for the isomerization of cis-alkenyl compounds to their trans-isomers). In this method, the above-described object is accomplished by reacting a cis-alkenyl compound in the presence of nitric acid used as the sole catalyst.

7-Vinyldecyl acetate, novel inhibitor of pheromonal attraction in the false codling moth, cryptophlebia leucotreta

It was found that 7-vinyldecyl acetate, a by-product of the synthesis of one of the constituents of the sex attractant of the false codling moth, Cryptophlebia leucotreta, effectively disrupts the attraction of male moths to virgin females or to synthetic lures.