149846-22-0

Basic information

• Product Name: (Z)-1-benzyl-5-bromooxoindolin-3-ylidene acetophenone
• CAS NO: 149846-22-0
• Molecular Weight: 418.29
• Mol File: 149846-22-0.mol

Chemical Properties

• CAS DataBase Reference: (Z)-1-benzyl-5-bromooxoindolin-3-ylidene acetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-benzyl-5-bromooxoindolin-3-ylidene acetophenone(149846-22-0)
• EPA Substance Registry System: (Z)-1-benzyl-5-bromooxoindolin-3-ylidene acetophenone(149846-22-0)

Safety Data

• Hazardous Substances Data: 149846-22-0(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 79183-44-1 1-benzyl-5-bromoisatin 
• 149846-19-5 (E)-1-benzyl-5-bromo-3-(2-oxo-2-phenylethylidene)indolin-2-one 

Relevant articles and documents

RETENTION OF THE CONFIGURATION OF OXOINDOLIN-3-YLIDENE DIPOLAROPHILES IN THE REACTION WITH AZOMETHINE YLIDES FROM NINHYDRIN AND SECONDARY AMINO ACIDS

The reaction of ninhydrin with sarcosin or proline gives azomethine ylides that can be trapped by (E)- or (Z)-oxoindolin-3-ylidene acetophenones. The configuration of the adducts can be assigned on the basis of NOE and Eu(fod)3 NMR experiments. The regiochemistry of the 1,3-dipolar cycloaddition is controlled by FMOs, while the configuration derives from the less hindered transition state. Under thermal conditions, some kinetically controlled products revert to dipole and dipolarophile that react to give the thermodynamically stable products.