CAS: 20307-83-9; β-Sesquiphellandrene

上下游产品

4-[(1S)-1,5-Dimethylhex-4-Enyl]Cyclohex-2-En-1-One 343239-55-4

📜(3S,6R,7S)-1,10-Bisaboladien-3-Ol置于吡啶,三氯氧磷体系中,用36%的收率获得β-倍半水芹烯
参考文献:Discovery Of The Aggregation Pheromone Of The Brown Marmorated Stink Bug (Halyomorpha Halys) Through The Creation Of Stereoisomeric Libraries Of 1-Bisabolen-3-Ols
标题:Discovery Of The Aggregation Pheromone Of The Brown Marmorated Stink Bug (Halyomorpha Halys) Through The Creation Of Stereoisomeric Libraries Of 1-Bisabolen-3-Ols
摘要:We Describe A Novel And Straightforward Route To All Stereoisomers Of 1,10-Bisaboladien-3-Ol And 10,11-Epoxy-1-Bisabolen-3-Ol Via The Rhodium-Catalyzed Asymmetric Addition Of Trimethylaluminum To Diastereomeric Mixtures Of Cyclohex-2-Enones 1 And 2. The Detailed Stereoisomeric Structures Of Many Natural Sesquiterpenes With The Bisabolane Skeleton Were Previously Unknown Because Of The Absence Of Stereoselective Syntheses Of Individual Stereoisomers. Several Of The Bisabolenols Are Pheromones Of Economically Important Pentatomid Bug Species. Single-Crystal X-Ray Crystallography Of Underivatized Triol 13 Provided Unequivocal Proof Of The Relative And Absolute Configurations. Two Of The Epoxides,(3S,6S,7R,10S)-10,11-Epoxy-1-Bisabolen-3-Ol (3) And (3R,6S,7R,10S)-10,11-Epoxy-1-Bisabolen-3-Ol (4),Were Identified As The Main Components Of A Male-Produced Aggregation Pheromone Of The Brown Marmorated Stink Bug,Halyomorpha Halys,Using Gc Analyses On Enantioselective Columns. Both Compounds Attracted Female,Male,And Nymphal H. Halys In Field Trials. Moreover,Mixtures Of Stereoisomers Containing Epoxides 3 And 4 Were Also Attractive To H. Halys,Signifying That The Presence Of Additional Stereoisomers Did Not Hinder Attraction Of H. Halys And Relatively Inexpensive Mixtures Can Be Used In Monitoring,As Well As Control Strategies. H. Halys Is A Polyphagous Invasive Species In The U.S. And Europe That Causes Severe Injury To Fruit,Vegetables,And Field Crops And Is Also A Serious Nuisance Pest.
Doi:10.1021/np5003753

专利信息

专利号:US-7175871-B2
优先权日:2002-07-15
标题:Acyclic enol ethers, isomers thereof, organoleptic uses thereof and processes for preparing same
发明人：MOOKHERJEE BRAJA DULAL; NARULA ANUBHAV P S; PATEL SUBHA M; ARRUDA EDWARD MARK; MERRITT PATRICK M
权利人:INT FLAVORS & FRAGRANCES INC
摘要:Described are synthetically produced substantially pure enol ether compositions which are cis and/or trans isomers of enol ethers having the structures: n nwherein R 1 is C 4 –C 10 straight chain alkyl or C 9 8-alkenyl; and wherein R 2 is C 1 –C 4 alkyl, C 3 –C 4 2-alkenyl, C 4 3-alkenyl or C 10 non-allenic alkadienyl and uses thereof in imparting, augmenting or enhancing the aroma and/or taste of a consumable material such as a perfume composition, a cologne, a perfumed article such as a soap, cosmetic, hair preparation or detergent, a foodstuff, a chewing gum or an alcoholic or non-alcoholic beverage such as a carbonated beverage or fruit liquer. Also described is a process for synthesis of such enol ethers by means of (i) first forming an acetal having the structure:n R 1 —CH 2 —CH(OR 2 ) 2 n(ii) then carrying out a thermal decomposition reaction at pH<7 and then (iii) fractionally distilling the resulting reaction product to provide the enol ether.