89996-92-9

Basic information

• Product Name: 2-Pentenoic acid, 2-methyl-4-phenyl-, methyl ester, (Z)-
• CAS NO: 89996-92-9
• Molecular Formula: C13H16O2
• Molecular Weight: 204.269
• Mol File: 89996-92-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Pentenoic acid, 2-methyl-4-phenyl-, methyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentenoic acid, 2-methyl-4-phenyl-, methyl ester, (Z)-(89996-92-9)
• EPA Substance Registry System: 2-Pentenoic acid, 2-methyl-4-phenyl-, methyl ester, (Z)-(89996-92-9)

Safety Data

• Hazardous Substances Data: 89996-92-9(Hazardous Substances Data)

Upstream product

• 34713-70-7 2-Phenylpropanal 
• 86581-80-8 diphenyl phosphinoxy-2-propionate de methyle 
• 140184-84-5 2-Triphenylstannanyl-propionic acid methyl ester 
• 29668-62-0 methyl 2-(diethoxyphosphoryl)propanoate 

Downstream Products

• 136066-30-3 4-Methylene-5-(1-phenylethyl)-1,2-dioxolan-3-one 
• 127909-82-4 2-Methyl-3-(1-phenyl-ethyl)-oxirane-2-carboxylic acid methyl ester 

Relevant articles and documents

Intrazeolite photooxygenation of chiral alkenes. Control of facial selectivity by confinement and cation-π interactions

Depending on the nature of the substituents on the stereogenic carbon atom, the ene reaction of singlet oxygen with several chiral alkenes by confinement within thionin-supported zeolite NaY, may exhibit significant changes on facial selectivity by comparison to their photooxygenation reaction in solution. It is proposed that, apart from the conformational consequences as a result of the alkene confinement within the zeolite cavities, a synergism between Na+-π interactions and singlet oxygen-Na+ interactions plays a significant role in the transition states of ene hydroperoxidation. Within NaY, the diastereoselectivity may significantly depend on the site selectivity, as probed through specific deuterium labelling of trisubstituted alkenes bearing a gem-dimethyl group. In certain cases, a remote stereogenic centre relative to the reacting double bond may induce enhanced diastereoselection and regioselectivity.

SYNTHESE STEREOSELECTIVE D'ESTERS α,β-ETHYLENIQUES α-METHYLES Z OU E PAR LA REACTION DE WITTIG-HORNER A PARTIR DE PHOSPHONATES OU D'OXYDES DE PHOSPHINE

The reaction of α-branched aldehydes with diethyl 1-carbomethoxyethyl phosphonate 1b in THF/nBuLi at low temperature leads stereoselectively to Z α-methyl α,β-unsaturated esters.From a linear aldehyde, the reaction is less stereoselective, while from α,β-unsaturated ones, the E isomers are predominantly formed in good yields.From diphenyl 1-carbomethoxyethyl phosphine oxide 2b, E α-methyl α,β-unsaturated esters are stereoselectively formed either in DMF/tBuOK or in phase transfer conditions, whatever the starting aldehyde is, also in good yields.This reagent can thus advantageously replace the corresponding P-ylid.In all cases, the reaction conditions are determined so that by-products formation is minimized.