7367-84-2

Usage

InChI:InChI=1/C12H22O2/c1-3-5-6-7-8-9-10-11-12(13)14-4-2/h8-9H,3-7,10-11H2,1-2H3/b9-8-

Upstream product

• 39924-57-7 (Z)-1-bromo-1-heptene 
• 140-88-5 ethyl acrylate 
• 50479-11-3 (3-ethoxycarbonylpropyl)triphenylphosphonium bromide 
• 66-25-1 hexanal 
• 2969-81-5 Ethyl 4-bromobutyrate 
• 26001-58-1 (Z)-oct-2-en-1-ol 
• 20739-58-6 2-octyn-1-ol 
• 25466-54-0 (Z)-1-bromo-2-octene 
• 30390-50-2 (Z)-4-decenal 
• 64-17-5 ethanol 
• 505-90-8 (Z)-dec-4-enoic acid 
• 90977-45-0 dec-4-enenitrile 
• 77899-12-8 diethyl 2(Z)-octenyl-malonate 

Downstream Products

• 7367-83-1 (Z)-dec-4-enoic acid methyl ester 
• 57074-37-0 (Z)-4-decen-1-ol 
• 54844-65-4 (Z)-6-heneicosen-11-one 
• 30390-50-2 (Z)-4-decenal 

Relevant academic research and scientific papers

Transforming Olefins into γ,δ-Unsaturated Nitriles through Copper Catalysis

We have developed a strategy to transform olefins into homoallylic nitriles through a mechanism that combines copper catalysis with alkyl nitrile radicals. The radicals are easily generated from alkyl nitriles in the presence of the mild oxidant di-tert-butyl peroxide. This cross-dehydrogenative coupling between simple olefins and alkylnitriles bears advantages over the conventional use of halides and toxic cyanide reagents. With this method, we showcase the facile synthesis of a flavoring agent, a natural product, and a polymer precursor from simple olefins.

Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional analysis tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

A New Synthesis of (Z)-Heneicos-6-en-11-one, Sex Pheromone of Douglas Fir Lepidoptera Orgyia pseudotsugata

2-Octyn-1-ol (II) on hydrogenation over Lindlar's catalyst provides (Z)-2-octen-1-ol (III).Conversion of III into the corresponding bromide (IV) with PBr3 and subsequent alkylation of ethyl monosodiomalonate with IV in benzene/DMF mixture gives the diester (V) in high yield.Removal of one carbethoxy group of (V) on heating with NaCl/H2O in DMSO affords ethyl 4(Z)-decenoate (VI) which on LAH reduction yields the carbinol (VII).Treatment of VII with PBr3 in dry ether furnishes the bromide (VIII) which easily forms Grignard reagent (IX) with dry Mg turnings in anhyd.THF.The reagent (IX) on reaction with undecanal furnishes (Z)-heneicos-6-en-11-ol (X).Oxidation of X with Corey's reagent provides (Z)-heneicos-6-en-11-one (I).