189191-25-1

Basic information

• Product Name: (1''S,2''S,4''R)-N-[4'-chloro-2-(2''-hydroxy-1'',3'',3''-trimethylbicyclo[2.2.1]hept-2''-yl)phenyl]-2,2-dimethylpropanamide
• Synonyms: (1''S,2''S,4''R)-N-[4'-chloro-2-(2''-hydroxy-1'',3'',3''-trimethylbicyclo[2.2.1]hept-2''-yl)phenyl]-2,2-dimethylpropanamide
• CAS NO: 189191-25-1
• Molecular Weight: 363.928
• Mol File: 189191-25-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1''S,2''S,4''R)-N-[4'-chloro-2-(2''-hydroxy-1'',3'',3''-trimethylbicyclo[2.2.1]hept-2''-yl)phenyl]-2,2-dimethylpropanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (1''S,2''S,4''R)-N-[4'-chloro-2-(2''-hydroxy-1'',3'',3''-trimethylbicyclo[2.2.1]hept-2''-yl)phenyl]-2,2-dimethylpropanamide(189191-25-1)
• EPA Substance Registry System: (1''S,2''S,4''R)-N-[4'-chloro-2-(2''-hydroxy-1'',3'',3''-trimethylbicyclo[2.2.1]hept-2''-yl)phenyl]-2,2-dimethylpropanamide(189191-25-1)

Safety Data

• Hazardous Substances Data: 189191-25-1(Hazardous Substances Data)

Upstream product

• 4695-62-9 fenchone 
• 65854-91-3 N-(4-chlorophenyl)-2,2-dimethylpropionamide 

Downstream Products

• 189191-26-2 N-[4-Chloro-2-((1S,2S,4R)-2-methoxy-1,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-phenyl]-2,2-dimethyl-propionamide 

Relevant articles and documents

Tandem Wagner-Meerwein rearrangement-carbocation trapping in the formation of chiral heterocyclic ring systems

Ortho lithiated protected anilines and phenols undergo exclusive addition to fenchone from the exo face. The corresponding adducts, under acidic conditions undergo cationic rearrangement followed by internal trapping of the new cation with amino, hydroxyl or methoxyl substituents to give enantiomerically pure chiral heterocyclic ring systems. The nature of the rearrangement is dependent on the donor group and ifs ability to stabilise a positive charge. With an amino donor group a product due to Wagner-Meerwein rearrangement is formed while with a methoxy donor group Nametkin rearrangement is the preferred pathway.