2833-20-7

Usage

Occurrence

Commonly found in various plant oils such as sunflower, safflower, and corn oil.

Uses

Food Industry: Utilized as a flavoring agent.
Cosmetics and Perfumery: Employed as a fragrance ingredient in perfumes and cosmetics.
Pharmaceuticals: Potential applications in pharmaceutical products.
Organic Synthesis: Acts as a precursor for the synthesis of other organic compounds.

Upstream product

• 42599-16-6 (E)-1-octen-1-ylboronic acid 
• 140-88-5 ethyl acrylate 
• 42516-28-9 ethyl (2E)-4-(diethoxyphosphoryl)crotonate 
• 111-71-7 heptanal 
• 1325759-00-9 C₁₀H₁₃F₆O₅P 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 14952-06-8 methyl (2E)-2-nonenoate 
• 111-66-0 oct-1-ene 
• 31930-34-4 ethyl (Z)-3-bromopropenoate 

Relevant academic research and scientific papers

Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation - Pd-catalyzed cross-coupling

All four stereoisomers (7-10) of ethyl undeca-2,4-dienoate were prepared in ≥98% isomeric purity by Pd-catalyzed alkenylation (Negishi coupling) using ethyl (E)- and (Z)-β-bromoacrylates. Although the stereoisomeric purity of the 2Z,4E-isomer (8) prepared by Suzuki coupling using conventional alkoxide and carbonate bases was ≤95%, as reported earlier, the use of CsF or nBu4NF as a promoter base has now been found to give all of 7-10 in ≥98% selectivity. Other widely known methods reveal considerable limitations. Heck alkenylation was satisfactory for the syntheses of the 2E,4E and 2E,4Z isomers of ≥98% purity, but the purity of the 2Z,4E isomer was ≤95%. Mutually complementary Horner-Wadsworth-Emmons and Still-Gennari (SG) olefinations are also of considerably limited scopes. Neither 2E,4Z nor 2Z,4Z isomer is readily prepared in ≥90% selectivity. In addition to (2Z,4E)-dienoic esters, some (2Z,4E,6E)- and (2Z,4E,6Z)-trienoic esters have been prepared in ≥98% selectivity by a newly devised Pd-catalyzed alkenylation-SG olefination tandem process. As models for conjugated higher oligoenoic esters, all eight stereoisomers for ethyl trideca-2,4,6-trienoate (23-30) have been prepared in ≥98% overall selectivity.

Palladium-catalyzed cross-coupling of aryl and alkenyl boronic acids with alkenes via oxidative addition of a carbon-boron bond to palladium(0)

Arylboronic acids react with alkenes in acetic acid at 25 deg C in the presence of a catalytic amount of palladium(II) acetate together with sodium acetate to give the corresponding aryl-substituted alkenes in high yields.Alkenylboronic acids react with alkenes under similar conditions to give the corresponding conjugated dienes stereospecifically, but the product yields are lower, compared with those from arylboronic acids.Similar treatment of sodium tetraphenylborate (NaBPh4) with alkenes also affords the corresponding phenylated alkenes in high yields together with biphenyl and benzene as side products.Oxidative addition of a carbon-boron bond to palladium(0), formed in situ, to give an organopalladium(II) species is assumed to be the key step of these cross-coupling reactions. Key words: Boronic acid; Aryl; Alkenyl; Alkene; Palladium; Oxidative addition

AN IMPROVED PROCEDURE FOR THE TWO CARBON HOMOLOGATION OF ESTERS TO α,β-UNSATURATED ESTERS

Treatment of esters with diisobutylaluminium hydride (DIBAL) in the presence of lithio-trialkylphosphonoacetate results in improved yields of the homologated α,β-unsaturated esters.The problematic overreduction, which has previously observed in the half reduction of esters using DIBAL, is minimal (3percent) under these conditions.