54664-98-1

Usage

InChI:InChI=1/C16H28O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-18-16(2)17/h4-7H,3,8-15H2,1-2H3/b5-4+,7-6+

Upstream product

• 917-64-6 methyl magnesium iodide 
• 55136-52-2 pent-2-yn-1-al 
• 80625-80-5 Acetic acid 9-(triphenyl-λ⁵-phosphanylidene)-nonyl ester 
• 50767-79-8 (9Z,11E)-9,11-tetradecadiene-1-yl acetate 
• 72553-58-3 (E,E)-9,11-tetradecadien-1-ol 
• 108-24-7 acetic anhydride 
• 945529-61-3 9,11-tetradecadien-1-ol 
• 87242-05-5 (Z)-11-(Tetrahydro-pyran-2-yloxy)-undec-2-en-1-ol 
• 19754-58-6 2-dec-9-ynyloxy-tetrahydro-pyran 
• 16666-78-7 propylidenetriphenylphosphorane 
• 71277-09-3 (Z)-10-Formyl-9-decenylacetat 
• 63024-87-3 (E)-11-Formyl-10-undecensaeure-methylester 
• 81744-94-7 7-tetrahydropyranyloxy-heptyl-magnesium chloride 
• 53596-83-1 1-tetrahydropyranyloxy-8-iodooctane 

Relevant academic research and scientific papers

Olefinic acetates, Δ-9,11-14:OAc and Δ-7,9-12:OAc used as sex pheromone components in three geometrid moths, Idaea aversata, I. straminata, and I. biselata (Geometridae, Lepidoptera)

Pheromone compounds so far identified from most geometrid moths consist of all-Z diene, triene, or tetraene hydrocarbons with chain lengths of C17 to C21, and their monoepoxide derivatives biosynthesized from linoleic and linolenic acids. The present study reports the occurrence of olefinic acetates as sex pheromones in three species of Geometridae. (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate found in female gland extracts of Idaea aversata elicited significant responses from conspecific male antennae in gas chromatography with electroantennographic detection (GC-EAD). In extracts of I. straminata, (Z,E)-7,9-dodecadienyl acetate, (E,Z)-7,9-dodecadienyl acetate, and (Z,Z)-7,9-dodecadienyl acetate were found, and the synthetic compounds elicited strong responses from conspecific male antennae. In the third species, I. biselata, only (Z,Z)-7,9- dodecadienyl acetate was found in the female extracts, and this compound elicited a strong EAD response from the conspecific male antenna. The identities of the pheromone components in I. aversata and I. straminata were further confirmed according to their characteristic ions after GC-MS analyses. Single sensillum recordings from I. aversata showed two types of pheromone-detecting sensilla present on the male antenna. One type contained two receptor neurons, one of which was specifically tuned to (Z,Z)-9,11- tetradecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. A second type contained one neuron responding to (Z,Z)-7,9-dodecadienyl acetate. The two types were clearly different also with respect to external morphology, the former being considerably longer and having a larger base diameter. Also in I. straminata two physiological types of sensilla could be distinguished. One type contained two neurons, one of which responded to (Z,Z)-7,9-dodecadienyl acetate, the other to (Z,E)-9,11-tetradecadienyl acetate. The second type contained one neuron, responding the (Z,Z)-7,9- dodecadienyl acetate. No correlation between external morphology and physiological response of the investigated sensilla was observed in I. straminata. In field tests, a two-component blend containing (Z,Z)-9,11- tetradecadienyl acetate and (Z,Z)-7,9-dodecadienyl acetate in a ratio of 10:1 was attractive to males of I. aversata. This two-component blend was also attractive to males of I. straminata, but in a ratio of 1:1. High numbers of male I. biselata were caught in traps baited with (Z,Z)-7,9-dodecadienyl acetate alone. The incorporation of deuterium labels into pheromone components after topical application of deuterium-labeled palmitic acid confirmed that the pheromone components of I. aversata could be synthesized from this precursor, as has been previously observed for acetate pheromone components of many other moth species. Our results suggest that an evolutionary reversal back to the production of palmitic acid-derived pheromone components has occurred within the geometrid subfamily Sterrhinae.

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.

A GENERAL AND STEREOSELECTIVE SYNTHESIS OF (E,E)-CONJUGATED DIENES.

Cis-2,5-disubstituted-2,5-dihydrothiophene-1,1-dioxides, generated by a retro Diels-Alder reaction, lead with high stereoselectivity to (E,E)-1,4-disubstituted-1,3-dienes.The efficiency of this method is illustrated by the synthesis of two dienic insect sex pheromones.

Simple, Stereospecific Syntheses of Some Insect Pheromones using the -Fe(CO)3 Protecting Group

(Diene)Fe(CO)3 complexes have been used for totally stereospecific syntheses of insect pheromones having (E)- and (E,E)-1,3-diene skeletons.

SYNTHESIS OF LOBESIA BOTRANA AND SPODOPTERA LITTORALIS NATURAL SEX-ATTRACTANTS

Starting from the coupling reaction of alkyl cuprates with 1-alkynyl-2-propenyl acetates, the title compounds were preparated by short convenient syntheses.