65638-74-6

Basic information

• Product Name: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-
• Synonyms: Z-Methyl-α-formamidocinnamat;(Z)-N-Formyldehydrophenylalanin-methylester;(Z)-methyl 2-formylamino-3-phenylacrylate
• CAS NO: 65638-74-6
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Mol File: 65638-74-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-(65638-74-6)
• EPA Substance Registry System: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-(65638-74-6)

Safety Data

• Hazardous Substances Data: 65638-74-6(Hazardous Substances Data)

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

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

Downstream Products

• 4289-95-6 N-formyl-phenylalanine 
• 71921-02-3 2-benzyl-2-formamidoacetic acid methyl ester 
• 119826-10-7 methyl (Z)-β-(1-imidazolyl)-α-isocyanocinnamate 
• 119826-10-7 methyl (E)-β-(1-imidazolyl)-α-isocyanocinnamate 
• 119825-90-0 methyl (E)-benzylthio α-formylaminocinnamate 
• 119825-89-7 methyl (Z)-benzylthio α-formylaminocinnamate 
• 119825-92-2 (E)-3-Ethylsulfanyl-2-formylamino-3-p-tolyl-acrylic acid methyl ester 
• 119825-91-1 (E)-3-Ethylsulfanyl-2-formylamino-3-p-tolyl-acrylic acid methyl ester 
• 119825-88-6 methyl (E)-β-ethylthio-α-formylaminocinnamate 
• 119825-87-5 methyl (Z)-β-ethylthio-α-formylaminocinnamate 
• 77642-79-6 4-methoxycarbonyl-2-oxo-5-phenylimidazoline 
• 119826-09-4 (E)-methyl β-benzyl-amino-α-isocyanociannamate 
• 119826-02-7 methyl β-benzylamino-α-formylaminocinnamate 
• 119826-05-0 (Z)-Methyl 3-bromo-2-isocyano-3-phenylacrylate 

Relevant articles and documents

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.

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