188578-76-9

Basic information

• Product Name: 2,5-Diazabicyclo[2.2.1]heptan-3-one,2-phenyl-,(1S)-(9CI)
• Synonyms: 2,5-Diazabicyclo[2.2.1]heptan-3-one,2-phenyl-,(1S)-(9CI)
• CAS NO: 188578-76-9
• Molecular Formula: C11H12N2O
• Molecular Weight: 0
• Product Categories: PIPERIDINE
• Mol File: 188578-76-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,5-Diazabicyclo[2.2.1]heptan-3-one,2-phenyl-,(1S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diazabicyclo[2.2.1]heptan-3-one,2-phenyl-,(1S)-(9CI)(188578-76-9)
• EPA Substance Registry System: 2,5-Diazabicyclo[2.2.1]heptan-3-one,2-phenyl-,(1S)-(9CI)(188578-76-9)

Safety Data

• Hazardous Substances Data: 188578-76-9(Hazardous Substances Data)

Usage

Appearance

White to off-white solid

Molecular weight

189.25 g/mol

Use

Catalyst and reagent in organic synthesis (especially in the production of pharmaceuticals and agrochemicals)

Unique structure and properties

Valuable tool in the development of new chemical processes and the preparation of complex molecules

Applications

Manufacture of polymers and specialty chemicals

Importance

Diverse uses in the chemical industry

Upstream product

• 51-35-4 4R-4-hydroxyproline 
• 188578-74-7 (2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-4-hydroxyprolinanilide 
• 96034-57-0 (2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid 
• 188578-75-8 2-Phenyl-5-(p-nitrobenzyloxycarbonyl)-2,5-diazabicyclo[2.2.1]heptan-3-one 

Relevant articles and documents

An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics

Treatment of anilides of N-protected (2S,4R)-4-hydroxyproline, e.g. 1, with thioacetic acid under Mitsunobu conditions gives, unexpectedly, 2,5-diazabicyclo[2.2.1]heptan-3-ones, e.g. 2, the products of intramolecular cyclisation. However, the less acidic N-benzylamides of these proline derivatives, e.g. 7, are not sufficiently acidic and the hydrazido anion generated in the Mitsunobu reaction displaces the activated hydroxy group in an intermolecular reaction to give 8. The bicyclic γ-lactams are potential analogues of the β-lactam antibiotics and suitable derivatives 9, 10,11 and 12 are found to be competitive inhibitors of class A and C β-lactamases, with Ki as low as 70 μM.