117869-43-9

Basic information

• Product Name: N-(endo-bicyclo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalanine
• CAS NO: 117869-43-9
• Molecular Weight: 285.343
• Mol File: 117869-43-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(endo-bicyclo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(endo-bicyclo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalanine(117869-43-9)
• EPA Substance Registry System: N-(endo-bicyclo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalanine(117869-43-9)

Safety Data

• Hazardous Substances Data: 117869-43-9(Hazardous Substances Data)

Upstream product

• 934-30-5 exo-5-norbornene-2-carboxylic acid 
• 63-91-2 L-phenylalanine 
• 27063-48-5 bicyclo[2.2.1]hept-5-ene-exo-2-carbonyl chloride 

Downstream Products

• 117835-13-9 (S)-2-[((1R,2R,4S)-Bicyclo[2.2.1]heptane-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester 
• 117835-13-9 (S)-2-[((1S,2S,4R)-Bicyclo[2.2.1]heptane-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester 
• 117835-11-7 methyl-N-(endo-bicylo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalaninate 
• 117835-11-7 methyl-N-(endo-bicylo<2.2.1>hept-5-en-2-carbonyl)-L-phenylalaninate 

Relevant articles and documents

Natural amino acids as chiral auxiliaries in asymmetric Diels-Alder reactions

To test whether α-amino acids can be efficient chiral auxiliaries in asymmetric Diels-Alder reactions, the chiral dienophile N-acryloyl-L-phenylalanine methyl ester was made to react with cyclopentadiene.Diastereofacial selectivity is to a great extent dependent on the Lewis acid used to promote the reaction; whereas moderate excesses of the (1R,2R)-cycloadduct were achieved with AlCl3, the reaction did not show diastereofacial selectivity when titanium catalysts were used.Moreover, with Ti(iPrO)4 a transesterification reaction, which leads to the isopropyl ester and competes with the Diels-Alder reaction, was observed.In spite of the stuctural similarity of this dienophile to the acrylate of (S)-ethyl lactate, it behaved very differently in the titanium-catalyzed reactions.