189098-29-1

Basic information

• Product Name: (6R,7S)-2-ACETYL-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE
• Synonyms: (6R,7S)-2-ACETYL-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE;2-Azabicyclo[2.2.1]hept-5-en-3-one, 2-acetyl-, (1R,4S)- (9CI);(1R,4S)-2-acetyl-2-aza-bicyclo[2.2.1]hept-5-en-3-one;(1R,4S)-2-Acetyl-2-azabicyclo[2.2.1]heptan-5-en-3-one
• CAS NO: 189098-29-1
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.16256
• Product Categories: ACETYLGROUP
• Mol File: 189098-29-1.mol

Chemical Properties

• Boiling Point: 287.6 °C at 760 mmHg
• Flash Point: 135.1 °C
• Appearance: /
• Density: 1.288 g/cm³
• Vapor Pressure: 0.00246mmHg at 25°C
• Refractive Index: 1.565
• CAS DataBase Reference: (6R,7S)-2-ACETYL-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (6R,7S)-2-ACETYL-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE(189098-29-1)
• EPA Substance Registry System: (6R,7S)-2-ACETYL-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE(189098-29-1)

Safety Data

• Hazardous Substances Data: 189098-29-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(6R,7S)-2-Acetyl-2-aza-bicyclo[2.2.1]hept-5-en-3-one is used as a key intermediate in the synthesis of various pharmaceuticals, primarily antibiotics. Its unique structure and functional groups allow for the development of drugs that target specific enzymes or biochemical pathways, contributing to the fight against bacterial infections.
Used in Organic Synthesis:
(6R,7S)-2-Acetyl-2-aza-bicyclo[2.2.1]hept-5-en-3-one is also used as a versatile intermediate in organic synthesis due to its chemical properties that enable a range of possible modifications. This makes it a valuable compound for creating new molecules with potential applications in various fields, including medicine, agriculture, and materials science.

InChI:InChI=1/C8H9NO2/c1-5(10)9-7-3-2-6(4-7)8(9)11/h2-3,6-7H,4H2,1H3

Upstream product

• 49805-30-3 2-azabicyclo[2.2.1.]hept-5-en-3-one 
• 200002-40-0 cis-2-acetyl-2-aza-bicyclo[2.2.1]hept-5-en-3-one 
• 162307-09-7 (+/-)-cis-2-acetyl-2-azabicyclo<2.2.1>hept-5-en-3-one 
• 108-24-7 acetic anhydride 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 

Downstream Products

• 255839-20-4 (1R,4S)-2-Acetyl-1-amino-4-(hydroxymethyl)-2-cyclopentene 
• 861897-34-9 (1R,4S,5R,6S)-2-acetyl-5,6-dihydroxy-2-azabicyclo-[2.2.1]heptan-3-one 
• 208179-45-7 (1S,2R,4S,5R)-6-Acetyl-3-oxa-6-aza-tricyclo[3.2.1.0^2,4]octan-7-one 

Relevant articles and documents

Method for preparing (1R,4S)-2-azabicyclo[2.2.1]hept-5-ene-3-one derivatives

A biotechnological method is described for preparing compounds of the general formulas wherein R1 is acyl or acyloxy and R2 is a hydrogen atom or C1-10 alkyl, comprising the conversion of a lactam of the general formula by means of a hydrolase in the presence of a nucleophile and in the presence of a base in a constant pH range. Also described is the subsequent conversion of the compound of general formula I into the optically active 1-amino-4-(hydroxymethyl)-2-cyclopentene of the formula

Process for preparing enantiomerically enriched N-derivatized lactams

The present invention relates to a process for the preparation of enantiomerically enriched N-derivatized (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-ones by use of an enzyme.

A practical enzymatic procedure for the resolution of N-substituted 2- azabicyclo[2.2.1]hept-5-en-3-one

A simple and efficient process for the enantioselective resolution of N- substituted 2-azabicyclo[2.2.1]hept-5-en-3-one has been developed using commercially available hydrolytic enzymes. This offers a practical approach for the preparation of enantiomerically pure N-substituted γ-lactams.

A highly efficient synthesis of the antiviral agent (+)-cyclaradine involving the regioselective cleavage of epoxide by neighboring participation

(+)-Cyclaradine, carbocyclic arabinofuranosyladenine having anti-HSV activity, has been synthesized from (-)-2-azabicyclo[2.2.1]hept-5-en-3-one in only seven steps. The method involves the novel ring cleavage of epoxide by neighboring participation.