103618-97-9

Basic information

• Product Name: methyl 2-amino-5-phenyl-(RS)-(E)-4-pentenoate
• Synonyms: methyl 2-amino-5-phenyl-(RS)-(E)-4-pentenoate
• CAS NO: 103618-97-9
• Molecular Weight: 205.257
• Mol File: 103618-97-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: methyl 2-amino-5-phenyl-(RS)-(E)-4-pentenoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-amino-5-phenyl-(RS)-(E)-4-pentenoate(103618-97-9)
• EPA Substance Registry System: methyl 2-amino-5-phenyl-(RS)-(E)-4-pentenoate(103618-97-9)

Safety Data

• Hazardous Substances Data: 103618-97-9(Hazardous Substances Data)

Upstream product

• 1234563-89-3 C₁₉H₁₉NO₂ 
• 219858-15-8 (E)-5-phenyl-2-nitropent-4-enoic acid methyl ester 
• 86537-61-3 ethyl cinnamylcarbonate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 210841-48-8 methyl (E)-2-(N-benzhydrylideneamino)-5-phenylpent-4-enoate 
• 103550-81-8 2-(Benzhydrylidene-amino)-3-phenyl-pent-4-enoic acid methyl ester 
• 103550-82-9 (E)-2-(Benzhydrylidene-amino)-5-phenyl-pent-4-enoic acid methyl ester 
• 66646-88-6 (E)-N-benzylideneglycine methyl ester 
• 4392-24-9 Cinnamyl bromide 
• 106625-69-8 ethyl (E)-3-phenyl-2-propenyl carbonate 

Downstream Products

• 128369-92-6 N-[4-(1-hydroxyiminoethyl)phenyl]-N'-[(1-methoxycarbonyl)-4-phenyl-3-butenyl]urea 
• 1234564-16-9 methyl (E)-2-(methoxycarbonylamino)-5-phenylpent-4-enoate 
• 52179-72-3 5-phenyl-1H-pyrrole-2-carboxylic acid methyl ester 
• 210841-57-9 methyl (E)-5-phenyl-2-(p-toluenesulfonylamino)pent-4-enoate 

Relevant articles and documents

Carbenium ion trapping using sulfonamides: an acid-catalysed synthesis of pyrrolidines by intramolecular hydroamination

Cyclisations of homoallylic sulfonamides proceed smoothly via carbenium ion generation using trifluoromethanesulfonic (triflic) acid, the ease of cyclisation being directly related to the ion stability to give good to excellent yields of the corresponding pyrrolidines. Both toluene- and nitrophenyl-sulfonyl groups are suitable for all substrates tested whereas the corresponding carbamates are only useful in cases of tertiary and highly stabilised carbenium ions. Polyene-derived sulfonamides can also be cyclised to the corresponding polycyclic systems in remarkably high yields, in reactions reminiscent of related cascades encountered in terpene biosynthesis.

The synthesis of 5-substituted proline derivatives and of 5-substituted pyrrole-2-carboxylates by 5-endo cyclisations featuring a method for effectively favouring these with respect to 5-exo cyclisations

Overall 5-endo cyclisations of the C-allylic glycine sulfonamides 5 lead to usually excellent yields of the 2,5-cis- or 2,5-trans-pyrrolidine-2-carboxylates 11 and 12 respectively, depending upon whether base is absent or present. While reductions to the corresponding pyrrolidine-2-methanols 13 proved efficient, subsequent eliminations of the elements of hydrogen iodide gave mixtures of products 14-16. Suitably positioned hydroxy groups compete successfully with the sulfonamide via a 5-exo cyclisation mode. However, when such a substrate contains a furan ring attached to the alkene function (21), then cyclisation does occur at the sulfonamide, presumably by participation of the furan oxygen, to give an iodopyrrolidine-2-methanol 13a. Finally, base-induced elimination of both hydrogen iodide and toluene-p-sulfinic acid from the initial iodopyrrolidines 11 and 12 leads to 5-substituted pyrrole-2-carboxylates 26. Overall, this sequence is complementary to the Kenner pyrrole synthesis.

SYNTHESIS OF α-AMINOACIDS BY CATALYTIC PALLADIUM (O) ALKYLATION OF BASES

Schiff bases 1 b, 1 c, 2 derived from glycine ester or aminoacetonitrile were alkylated with allylic acetates 3 a, 3 b or allylic carbonates 3 c, 3 d, 4 a, 4 b (under neutral conditions) in presence of catalytic amount of palladium (O).After hydrolysis higher and functionalized α-aminoesters were obtained in good yields (50 to 85 percent).