31502-19-9Relevant academic research and scientific papers
A concise synthesis of sex pheromone of mediterranean fruit fly, ceratitis capitata via lithiated carbanion derived from enephosphoramide
Olszewski, Tomasz Krzysztof,Grison, Claude
, p. 139 - 147 (2010)
A novel and versatile synthetic approach to the preparation of (E)-non-6-en-1-ol, a sex pheromone of the Mediterranean fruit fly, Ceratitis capitata, is presented. This pheromone can be viewed as potential active component for lures designed to control and eradication of Mediterranean fruit fly. The described protocol is a six-step reaction sequence producing the desired compound with 28% overall yield from commercially available and inexpensive starting material and total E stereoselectivity of the double bond present in final structure. The key to the success ofthe presented strategy is application oflithiated α-allylphosphoramido carbanions and their reaction with halogenated acetals.
Pheromones via Organoboranes. 2. Vinylic Organoboranes. 8. Applications of the General Stereoselective Synthesis of (E)-Disubstituted Alkenes via Thexylchloroborane-Dimethyl Sulfide to the Synthesis of Pheromones Containing an (E)-Alkene Moiety
Brown, Herbert C.,Lee, Hsiupu D.,Kulkarni, Surendra U.
, p. 5282 - 5286 (1986)
Various (E)-pheromones of the general structure (E)-X-alken-1-yl acetates, (E)-X-alken-1-ols, and (E)-X-alken-1-als have been prepared via thexylchloroborane-dimethyl sulfide (ThxBHCl*SMe2).Hydroboration of acetate-functionalized alkenes with ThxBHCl*SMe2 gives cleanly the corresponding thexylalkylchloroboranes (ThxBRCl, B).Hydridation of B with potassium triisopropoxyhydride (KIPBH) at -78 deg C gives cleanly the corresponding thexylalkylboranes (ThxBRH, C).These are quenched immediately with 1-halo-1-alkynes to give B-(cis-1-halo-1-alkenyl)thexylalkylboranes (D).Treatment of D with sodium methoxide results in the displacement of bromine by the alkyl group on boron to produce B-(trans-1-alkyl-1-alkenyl)thexylborinates (E).Protonolysis of E with acetic acid provides (E)-X-alken-1-yl acetates in high yields and in >99percent isomeric purities.Treatment of (E)-X-alken-1-yl acetates with base affords the corresponding (E)-X-alken-1-ols.Oxidation of (E)-X-alken-1-ols with dimethyl sulfoxide activated by oxalyl chloride or the complex of dimethyl sulfide and chlorine produces (E)-X-alken-1-als quantitatively.By properly choosing the starting functionalized alkenes and 1-halo-1-alkynes, various (E)-pheromones can be prepared easily.The present procedure appears to be general.There does not appear to be any limitation on the length of the carbon chain or the position of the double bond in the target molecules.
A general strategy for the stereocontrolled preparation of diverse 8- and 9-membered Laurencia -type bromoethers
Snyder, Scott A.,Treitler, Daniel S.,Brucks, Alexandria P.,Sattler, Wesley
, p. 15898 - 15901 (2011/11/13)
A unique procedure to effect a ring-expanding bromoetherification process is described, wherein tetrahydrofurans and tetrahydropyrans are smoothly transformed into 8- and 9-membered bromoethers in a regio- and stereocontrolled manner through the use of BDSB (bromodiethylsulfonium bromopentachloroantimonate). These products resemble the cores of the Laurencia C15 acetogenins. In light of the generality and effectiveness of the approach, this work provides a unique strategy for their laboratory preparation and may implicate a possible biosynthesis pathway.
Serine carbonates
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, (2008/06/13)
Serine carbonates of formula I are precursors for organoleptic compounds, masking agents and antimicrobial agents. Further they are alternative substrates for malodor producing enzymes. The symbols in formula I are defined in claim 1.
Compounds having protected hydroxy groups
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, (2008/06/13)
The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
Beta-ketoester compounds
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, (2008/06/13)
The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.
Ketone precursors for organoleptic compounds
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, (2008/06/13)
The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.
New and simple syntheses of the attractants of the female melon fly, dacus cucurbitee
Yen, Yao-Pin,Chen, Pao-Hsing
, p. 87 - 90 (2007/10/03)
The attractant of the female melon fly, (E)-6-nonenyl acetate, and the two analogs, (E)-7-dodecenyl acetate and (E)-7-decenyl acetate were synthesized via hydrozirconation to control the regioselective coupling reactions and resulted in good yields.
INSECT PHEROMONES AND THEIR ANALOGUES. XLV. SYNTHESIS OF MONO- AND DIENIC COMPONENTS OF INSECT PHEROMONES FROM ISOPROPYL NONA-3E,8-DIENOATE
Odinokov, V. N.,Ishmuratov, G. Yu.,Sokol'skaya, O. V.,Ladenkova, I. M.,Gubaidullin, L. Yu.,et al.
, p. 123 - 127 (2007/10/02)
Non-6E-en-1-ol, dodec-3E-en-1-yl acetate, and dodeca-7E,9Z-dien-1-yl acetate, which are components of sex pheromones of insects of the order Lepidoptera, have been synthesized from the readily accessible isopropyl nona-3E,8-dienoate.
Stereochemically controlled Synthesis of Unsaturated Alcohols by the Horner-Wittig Reaction
Ayrey, Peter M.,Bolton, Michael A.,Buss, Antony D.,Greeves, Nicholas,Levin, Daniel,et al.
, p. 3407 - 3418 (2007/10/02)
Single isomers (E or Z) of unsaturated alcohols with two to five carbon atoms between the double bond and the OH group may be made by the phosphine oxide version of the Horner-Wittig reaction.Hydroxyalkyldiphenylphosphine oxides react with aldehydes either directly or as silyl ethers to give a moderately Z-selective synthesis, while rearrangement of esters of the same alcohols by acyl transfer or acylation of alkyldiphenylphosphine oxides with lactones gives hydroxy ketones whose reduction and elimination leads to an E-selective synthesis.In most cases, separation of the diastereoisomers of the Horner-Wittig intermediates leads to the preparation of pure E- or Z-alkenols.
