156382-65-9

Basic information

• Product Name: Propanedioic acid, methyl[(2E)-3-phenyl-2-propenyl]-, diethyl ester
• CAS NO: 156382-65-9
• Molecular Formula: C17H22O4
• Molecular Weight: 290.359
• Mol File: 156382-65-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, methyl[(2E)-3-phenyl-2-propenyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, methyl[(2E)-3-phenyl-2-propenyl]-, diethyl ester(156382-65-9)
• EPA Substance Registry System: Propanedioic acid, methyl[(2E)-3-phenyl-2-propenyl]-, diethyl ester(156382-65-9)

Safety Data

• Hazardous Substances Data: 156382-65-9(Hazardous Substances Data)

Upstream product

• 21040-45-9 Cinnamyl acetate 
• 18424-77-6 sodium diethyl methylmalonate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 609-08-5 Diethyl methylmalonate 
• 62116-54-5 sodium diethyl methylmalonate 
• 50555-04-9 cinnamyl benzoate 
• 22023-25-2 1-phenylallyl benzoate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 7217-71-2 1-phenyl-2-propenyl acetate 

Relevant articles and documents

Bulky monodentate phosphoramidites in palladium-catalyzed allylic alkylation reactions: Aspects of regioselectivity and enantioselectivity

A series of bulky monodentate phosphoramidite ligands, based on biphenol, BINOL and TADDOL backbones, have been employed in the Pd-catalysed allylic alkylation reaction. Reaction of disodium diethyl 2-methyl malonate with monosubstituted allylic substrates in the presence of palladium complexes of the phosphoramidite ligands proceeds smoothly at room temperature. The regioselectivities observed depend strongly on the leaving group and the geometry of the allylic starting compounds. Mono-coordination occurs when these ligands are ligated in [Pd(allyl)(X)] complexes (allyl=C3H 5, 1-CH3C3H4, 1-C6H 5C3H4, 1,3-(C6H5) 2C3H3; X=Cl, OAc). The solid-state structure determined by X-ray diffraction of [Pd(C3H5)(1)(Cl)] reveals a non-symmetric coordination of the allyl moiety, caused by the stronger trans influence of the phosphoramidite ligand relative to X-. In all of these complexes, the syn,trans isomer is the major species present in solution. Because of fast isomerisation and high reactivity of the syn,cis complex, the major product formed upon alkylation is the linear product, especially for monosubstituted phenylallyl substrates in the presence of halide counterions. In the case of biphenol- and BINOL-based phosphoramidites, however, a strong memory effect is observed when 1-phenyl-2-propenyl acetate is employed as the substrate. In this case, nucleophilic attack competes effectively with the isomerisation of the transient cinnamylpalladium complexes. The asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate afforded the chiral product in up to 93% ee. Substrates with smaller substituents gave lower enantioselectivities. The observed stereoselectivity is explained in terms of a preferential rotation mechanism, in which the product is formed by attack on one of the isomers of the intermediate [Pd{1,3-(C6H5) 2C3H3}(L)-(OAc)] complex.

Direct Allylation of Active Methylene Compounds with Allylic Alcohols by Use of Palladium/Phosphine-Borane Catalyst System

The C?C bond formation between active methylene compounds and allylic alcohols has been newly developed by using a palladium complex as a catalyst together with a phosphine-borane ligand. The best phosphine-borane ligand for this direct allylation has bee

Enantioselective total synthesis of (+)-ophiobolin A

The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the