103541-16-8

Basic information

• Product Name: 2-Oxa-5-azabicyclo[2.2.1]heptan-6-one,5-methyl-3,7-diphenyl-, (1S,3R,4S,7R)-
• Synonyms: 2-Oxa-5-azabicyclo[2.2.1]heptan-6-one,5-methyl-3,7-diphenyl-, [1S-(exo,anti)]-; (-)-Dehydroclausenamide;Cycloclausenamide
• CAS NO: 103541-16-8
• Molecular Formula: C18H17 N O2
• Molecular Weight: 279.338
• Mol File: 103541-16-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Oxa-5-azabicyclo[2.2.1]heptan-6-one,5-methyl-3,7-diphenyl-, (1S,3R,4S,7R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxa-5-azabicyclo[2.2.1]heptan-6-one,5-methyl-3,7-diphenyl-, (1S,3R,4S,7R)-(103541-16-8)
• EPA Substance Registry System: 2-Oxa-5-azabicyclo[2.2.1]heptan-6-one,5-methyl-3,7-diphenyl-, (1S,3R,4S,7R)-(103541-16-8)

Safety Data

• Hazardous Substances Data: 103541-16-8(Hazardous Substances Data)

Upstream product

• 79898-19-4 (2R,3S)-3-phenyloxiranecarboxylic acid 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 130273-47-1 (3R,4S,5R)-neoclausenamidone 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 130202-78-7 (2R,3S)-N-methyl-N-(β-hydroxyphenylethyl)-3-phenyl-2,3-epoxypropionamide 
• 130202-79-8 (2R,3S)-2,3-Epoxy-N-methyl-N-phenacyl-3-phenylpropionamide 
• 68579-60-2 2-(methylamino)-1-phenylethanol 
• 130202-81-2 7-O-tosylneoclausenamide 

Relevant articles and documents

Asymmetric synthesis of (-)-dehydroclausenamide

Asymmetric synthesis of (-)-dehydroclausenamide 1 by scheme 2 was reported. Sharpless epoxidation was applied to cinnamyl alcohol for introduction of two desired chiral centers and the potential hydroxyl group. The key intermediate, γ-lactam (-)-5, was obtained by regio-selective intramolecular cyclization of (-)-6. Subsequent stereo-selective reduction was achieved by reducing C3-tetrahydropyranyl ether of (-)-5. The title natural product was then obtained by successive tosylation, hydrolysis and cyclization.