33956-49-9Relevant academic research and scientific papers
Insect pheromones and their analogs I. Synthesis of the sex attractant of the codling moth
Tolstikov,Dzhemilev,Khusnutdinov
, p. 101 - 102 (1978)
The synthesis of the sex attractant of the codling moth Laspeyresia pomonella has been performed using as the initial compounds linear dimers of butadiene with methyl acrylate.
A GENERAL AND STEREOSELECTIVE SYNTHESIS OF (E,E)-CONJUGATED DIENES.
Bloch, R.,Abecassis, J.
, p. 1247 - 1250 (1983)
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.
Synthesis of dodeca-8E,10E-dien-1-ol - The sex pheromone of Laspeyresia pomonella via the acetolysis of 4-propenyl-1,3-dioxane
Shakova,Zorin,Musavirov,Safarov,Muslukhov,Kharisov,Ishmuratov,Rakhmankulov
, p. 582 - 584 (1996)
A new scheme has been developed for the synthesis of dodeca-8E,10E-dien-1-ol (the sex pheromone of the codling moth) from sorbyl acetate, available from 4-propenyl-1,3-dioxane through the intermediate diacetate of 3-propenyl-2-oxapentane-1,5-diol.
Stereoselective Cross-Coupling of Grignard Reagents and Conjugated Dienylbromides using Iron Salts with Magnesium Alkoxides
Chourreu, Pablo,Gayon, Eric,Guerret, Olivier,Guillonneau, Lo?c,Lefèvre, Guillaume
supporting information, p. 4701 - 4706 (2021/09/10)
A convenient procedure allowing iron-catalyzed cross-coupling of alkyl or aryl Grignard reagents and conjugated dienyl bromides is reported, relying on the use of cheap and non-toxic magnesium alkoxides as sole additives. An excellent stereoselectivity is observed in the alkyl-dienyl series. This sequence has been applied to the synthesis of the sex pheromone of codling moth, illustrating its applicability for obtaining targets of industrial interest. Preliminary mechanistic studies carried out on the aryl-dienyl cross-coupling suggest that in situ generated ate homoleptic organoiron(II) species act as catalytically relevant intermediates. A modified preparative method for the realization of THF solutions of dienyl bromides as “ready-to-use” coupling partners is also discussed, circumventing the thermal instability of those derivatives.
Synthesis method of laspeyresia pomonella sex pheromone
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Paragraph 0030; 0037; 0038; 0039; 0046; 0047, (2019/09/17)
The invention relates to a synthesis method of laspeyresi pomonella sex pheromone. The method comprises the steps as follows: (1) methanol is added to methyl sorbate as a raw material, and an intermediate A sorbic alcohol is obtained through 5% palladium-carbon catalytic hydrogenation reduction; (2) the intermediate A sorbitol obtained in (1) and acetic anhydride are subjected to a reaction in ethyl acetate, triethylamine and water to obtain an intermediate B sorbic acetate; (3) 6-chlorohexanol is subjected to a reaction with trimethylchlorosilane in toluene in the presence of ethyl acetate and triethylamine, after the reaction, water is added, stirring and layering are performed, and an intermediate C6-chlorohexanol trimethylsilyl ester is obtained; (4) the intermediate B sorbic acetate and the intermediate C6-chlorohexanol trimethylsilyl ester are subjected to a reaction with sodium sand in a toluene solution, then, water and sulfuric acid are dropwise added, layering and rectification are performed, and a target product E8,E10-dodecadiene-1-ol is obtained. The synthesis method has the advantages as follows: the laspeyresi pomonella sex pheromone is synthesized from available rawmaterials, the reaction route is short, and the selectivity and product yield can be increased.
SYNTHESIS OF PHEROMONES AND RELATED MATERIALS VIA OLEFIN METATHESIS
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, (2018/09/12)
Methods for preparation of olefins, including 8- and 11-unsaturated monoenes and polyenes, via transition metathesis-based synthetic routes are described. Metathesis reactions in the methods are catalyzed by transition metal catalysts including tungsten-, molybdenum-, and ruthenium-based catalysts. The olefins include insect pheromones useful in a number of agricultural applications.
(8E, 10E) - 8,10-dodecadienol-1-ol for the preparation of
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Paragraph 0024; 0025, (2017/08/04)
The invention discloses a preparation method of (8E, 10E)-8, 10-dodecadienol-1-alcohol. The method comprises the steps of: reacting 6-chlorohexanol with trimethylchlorosilane in the presence of methyl tertiary butyl ether and triethylamine at 0 to 5 DEG C to obtain chloride trimethylethoxysilane; then performing the Grignard reaction on the chloride trimethylethoxysilane to obtain a Grignard agent; and reacting (2E, 4E)-2, 4-hexadiene-1-dryocrassyl acetate with the Grignard agent to obtain (8E, 10E)-8, 10-dodecadienol-1-triethoxysilane; and finally hydrolyzing the (8E, 10E)-8, 10-dodecadienol-1-triethoxysilane to obtain (8E, 10E)-8, 10-dodecadienol-1-alcohol. According to the preparation method, both the purity and the yield of hydroxy-protecting reaction product are relatively high; and the initiating success rate of the Grignard reaction is relatively high, the purity of the coupling reaction product is high.
SYNTHESIS OF OLEFINIC ALCOHOLS VIA ENZYMATIC TERMINAL HYDROXYLATION
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Paragraph 0315; 0320, (2016/01/30)
In certain aspects, the present invention provides methods for producing terminally hydroxylated alkenes and alkynes by contacting an unsaturated or saturated hydrocarbon substrate with a hydroxylase enzyme. Exemplary terminal hydroxylases useful for carrying out the methods of the invention exhibit strong selectivity towards one terminal carbon of a hydrocarbon substrate and include, but are not limited to, non-heme diiron alkane monooxygenases, cytochromes P450 (e.g., cytochromes P450 of the CYP52 and CYP153 family), as well as long chain alkane hydroxylases. In some embodiments, the terminally hydroxylated alkene or alkyne is further converted to a terminal alkenal. In certain embodiments, terminally hydroxylated alkenes and alkynes are useful as insect pheromones which modify insect behavior. In other embodiments, terminally hydroxylated alkenes and alkynes are useful intermediates for producing pheromones via acetylation or oxidation of the alcohol moiety.
Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates
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Page/Page column 6, (2010/05/13)
Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.
Metathesis syntheses of pheromones or their components
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, (2008/06/13)
The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, the major component of the Peach Twig Borer pheromone; (5R,6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9,Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenyl formate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenyl acetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate, the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employ a Class I-IV metathesis catalyst, entail few reaction steps, use generally commercially available starting materials, and have relatively short process times. These syntheses produce good yields without the need for expensive or sophisticated equipment. The invention also provides an inexpensive route for producing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxy alkenes and alpha-omega-dihalides to yield omega-haloalkenols, which are easily converted into omega-haloalkanols under traditional hydrogenation methods.
