163807-60-1

Basic information

• Product Name: Carbonic acid, ethyl (2E)-1-methyl-3-phenyl-2-propenyl ester
• CAS NO: 163807-60-1
• Molecular Formula: C13H16O3
• Molecular Weight: 220.268
• Mol File: 163807-60-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Carbonic acid, ethyl (2E)-1-methyl-3-phenyl-2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic acid, ethyl (2E)-1-methyl-3-phenyl-2-propenyl ester(163807-60-1)
• EPA Substance Registry System: Carbonic acid, ethyl (2E)-1-methyl-3-phenyl-2-propenyl ester(163807-60-1)

Safety Data

• Hazardous Substances Data: 163807-60-1(Hazardous Substances Data)

Upstream product

• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 7302-00-3 (E)-1,3-diphenyl-1-butene 
• 405551-16-8 methyl (E)-2-amino-3-methyl-5-phenylpent-4-enoate 
• 405551-17-9 methyl (E)-3-methyl-5-phenyl-2-(4-tolylsulfonylamino)pent-4-enoate 
• 89649-58-1 methyl 3-methyl-5-phenylpyrrole-2-carboxylate 
• 200191-40-8 (E)-dimethyl 2-(4-phenylbut-3-en-2-yl)malonate 
• 115404-72-3 dimethyl <1-phenyl-2(E)-butenyl>malonate 
• 100017-29-6 dimethyl (1R,2E)-(1-phenylbut-2-en-1-yl)malonate 
• 405551-14-6 methyl (E)-2-(N-benzhydrylideneamino)-5-phenyl-3-methylpent-4-enoate 

Relevant articles and documents

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.