65638-74-6

Usage

Properties

1. Chemical compound name: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-
2. Commonly known as: methyl (Z)-2-(formylamino)-3-phenylacrylate
3. Methyl ester derivative of 2-(formylamino)-3-phenylpropenoic acid
4. Z configuration: Substituents are on the same side of the double bond
5. Used in organic synthesis and pharmaceutical research
6. Potential uses in pharmaceutical and agrochemical development

Specific content

1. Chemical structure: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-
2. Unique properties: may have toxic or irritant properties
3. Handling: important to handle and use with care
4. Usage: development of pharmaceuticals and agrochemicals
5. Importance: due to its unique chemical structure and properties.

Upstream product

• 39687-95-1 isocyanoacetic acid methyl ester 
• 100-52-7 benzaldehyde 
• 108-86-1 bromobenzene 
• 44804-84-4 2-(formamido)acrylic acid methyl ester 
• 591-50-4 iodobenzene 

Downstream Products

• 1265278-17-8 (Z)-methyl β-bromo-α-formylaminocinnamate 
• 119825-78-4 (E)-methyl β-bromo-α-formylaminocinnamate 
• 76202-88-5 (Z)-methyl 2-isocyano-3-phenylacrylate 
• 119826-01-6 Methyl 1-benzyl-5-phenylimidazole-4-carboxylate 
• 119826-05-0 (Z)-Methyl 3-bromo-2-isocyano-3-phenylacrylate 
• 119826-02-7 methyl β-benzylamino-α-formylaminocinnamate 
• 119826-09-4 (E)-methyl β-benzyl-amino-α-isocyanociannamate 
• 77642-79-6 4-methoxycarbonyl-2-oxo-5-phenylimidazoline 
• 119825-87-5 methyl (Z)-β-ethylthio-α-formylaminocinnamate 
• 119825-88-6 methyl (E)-β-ethylthio-α-formylaminocinnamate 
• 119825-91-1 (E)-3-Ethylsulfanyl-2-formylamino-3-p-tolyl-acrylic acid methyl ester 
• 119825-92-2 (E)-3-Ethylsulfanyl-2-formylamino-3-p-tolyl-acrylic acid methyl ester 
• 119825-89-7 methyl (Z)-benzylthio α-formylaminocinnamate 
• 119825-90-0 methyl (E)-benzylthio α-formylaminocinnamate 

Relevant academic research and scientific papers

Enantioselective Rh-catalyzed hydrogenation of N-formyl dehydroamino esters with monodentate phosphoramidite ligands

Enantioselectivities up to >99% ee were achieved in the rhodium-catalyzed asymmetric hydrogenation of N-formyl dehydroamino esters using monodentate phosphoramidites as chiral ligands. The substrates were synthesized by condensation of methyl isocyanoacetate with a range of aldehydes and with cyclohexanone. A highly convenient multigram scale one step synthesis of methyl 2-(formamido)acrylate was developed. This compound was used in the synthesis of methyl 2-(formamido)cinnamate via a solvent free Heck reaction. Moreover, full conversion and >99% ee were obtained in 1 h in the hydrogenation of methyl 2-(formamido)acrylate with 0.2 mol% catalyst and 2 bar hydrogen pressure. The versatility of the formyl protection was established by its removal under mild conditions.

(Z)-selective β-bromination of N-formyl-α,β-dehydroamino acid esters

Stereoselective β-bromination of N-formyl-α,β-dehydroamino acid esters 5 was investigated. A reaction of 5 with NBS afforded α-bromo-N-formylimines 10 which successively isomerized to give β-bromo-N-formyl-α,β-dehydroamino acid esters 4. The migration of the double bond of the intermediates 10 with bulky substituents at the β-position resulted in highly stereoselective formation of (Z)-4, while that of the substrates with less bulky substituents proceeded non-stereoselectively. A mechanism of the stereoselective bromination was proposed on the basis of semiempirical calculations using AM1.

SYNTHESIS OF Β-FUNCTIONALIZED α,β-DEHYDROAMINO ACID DERIVATIVES

β-functionalized α,β-unsaturated amino acids were synthesized by an addition-elimination pathway.Reaction of methyl β-bromo-α-formylaminoacrylates ( 3a-e ), which were prepared by the condensation of methyl isocyanoacetate ( 1 ) with aldehydes followed by