35148-19-7

Usage

InChI:InChI=1/C14H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14(2)15/h4-5H,3,6-13H2,1-2H3/b5-4+

Upstream product

• 16974-34-8 Δ⁹-Dodecenyl acetate 
• 127-08-2 potassium acetate 
• 83748-50-9 1-chloro-9E-dodecene 
• 91856-11-0 Δ⁹-dodecen-1-ol 
• 108-24-7 acetic anhydride 
• 35237-62-8 (E)-9-dodecen-1-ol 
• 112983-60-5 1-tert-Butoxy-E-9-dodecene 
• 75-36-5 acetyl chloride 
• 63281-96-9 (E)-1-bromo-3-hexene 
• 68797-94-4 1-acetoxy-6-bromohexane 
• 53596-73-9 1-Acetoxy-9-dodecyne 
• 31502-19-9 (E)-6-nonen-1-ol 
• 55362-80-6 9-bromononan-1-ol 
• 1576-96-1 (E)-2-penten-1-ol 

Relevant academic research and scientific papers

Pheromones of insects and their analogs. LIV. Synthesis of dodec-9e-en-1-ol and its acetate - Components of the sex pheromone of Sparganothis pilleriana

Using the Claisen rearrangement in the construction of a double bond with the E configuration, we have synthesized dodec-9E-en-1-ol and its acetate, which are components of the sex pheromone of Sparganothis pilleriana.

Synthesis of E-9-dodecen-1-yl acetate using organomanganese reagents

The Grignard reagent obtained from 2-(6-bromohexyloxy)-tetrahydropyrane, by treatment with anhydrous manganese(II) chloride was transformed to the corresponding organomanganese reagent, which was coupled with E-1-bromo-3-hexene by treatment with anhydrous manganese chloride. Further deprotection and acetylation furnished E-9-dodecen-1-yl acetate. A second procedure involved the coupling of E-3-hexenylmanganese bromide and 6-bromohexyl acetate. Coupling reactions were carried out at 0 °C, using tetrahydrofurane and N-methylpyrrolidone as co-solvent.

A chemoselective reduction of alkynes to (E)-alkenes

The trans reduction of all types of alkynes to give (E)-olefins is achieved through a two-stage trans hydrosilylation and protodesilylation. Reaction of an alkyne and a silane with the ruthenium catalyst [Cp*Ru(MeCN)3]PF6 results in

Preparation of stereochemically pure E- and Z-alkenoic acids and their methyl esters from bicyclo[n.1.0]alkan-1-ols. Application in the synthesis of insect pheromones

Oxidative cleavage of exo- and endo-alkyl- and hydroxyalkyl-substituted bicyclo[n.1.0]alkan-1-ols with (diacetoxy-λ3-iodanyl)benzene gave the corresponding methyl alkenoates exclusively with E or Z configuration of the double bond. This reaction was used as the key stage in the syntheses of stereoisomerically pure components of pest insect pheromones: (E)-dodec-9-en-1-yl acetate (European pine shoot moth Rhyacionia buoliana), (Z)-tetradec-11-en-1-yl acetate (European oak leafroller Tortrix viridana), and (3E,8Z,11Z)-tetradeca-3,8,11-trien-1-yl acetate (tomato leafminer Tuta absoluta).

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.

Pheromones of insects and their analogs. LII. Sythesis of dodec-9-en-1-yl and tetradec-11-en-1-yl acetates from the products of the partial ozonolysis of cycloocta-1z,5z-diene and cyclodeca-1e,5z-diene

A new approach to the synthesis of octane-1,8-and decane-1,10-diols based on the partial ozonolysis of cyclic oligomers has been developed.

An electrochemical approach to some insect pheromones with (E)-alkene moiety

An easy access to some Lepidopteran pheromones containing (E)-alkene moiety via anodic oxidation of a partially neutralized mixture of trans-3-alkenoic acids and methyl hydrogen carboxylates has been described.

SIMPLE SYNTHESIS OF ACETOGENIN TRANSOID INSECT PHEROMONES STARTING FROM ACETYLCYCLOPROPANE

A highly effective synthesis of a series of alkyl and 1-alkenyl cyclopropyl ketones, which are key components in the complete synthesis of a large number of transoid lepidoptera pheromones, has been developed, based on the alkylation of N-cyclohexyl-1-cyclopropylethylideneimine or its condensation with aldehydes.

Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones

Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.