134003-03-5

Basic information

• Product Name: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE
• Synonyms: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE;(1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE 95%, (98% E.E.);(1s,4R)-2-Azabicyclo[2.2.1]heptan-3-one, 95%, ee:98%;(1S,4R)-2-Azabicyclo[2.2.1]heptan-3-one, 98% ee
• CAS NO: 134003-03-5
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14
• Mol File: 134003-03-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 76.2 °C
• Boiling Point: 208.27°C (rough estimate)
• Flash Point: 160.9°C
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.0656 (rough estimate)
• Vapor Pressure: 0.00215mmHg at 25°C
• Refractive Index: 1.4729 (estimate)
• CAS DataBase Reference: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE(134003-03-5)
• EPA Substance Registry System: (1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE(134003-03-5)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 134003-03-5(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly yellow crystalline powder

InChI:InChI=1/C6H9NO/c8-6-4-1-2-5(3-4)7-6/h4-5H,1-3H2,(H,7,8)/t4-,5+/m1/s1

Upstream product

• 24647-29-8 2-Azabicyclo[2.2.1]heptan-3-one 
• 49805-30-3 racemic 2-azabicyclo[2.2.1]hept-5-en-3-one 
• 79200-56-9 (-)-2-azabicyclo[2.2.1]hept-5-en-3-one 
• 95936-41-7 (-)-6endo,7anti-Dibromo-2-azabicyclo<2.2.1>heptan-3-one 
• 130931-83-8 (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one 

Downstream Products

• 151792-53-9 tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 
• 180323-49-3 (1R,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride 
• 625108-11-4 C₇H₁₃NO₂ 
• 674303-50-5 (1S,9R)-2,7-diazatricyclo[7.2.1.0^2,8]dodec-7-ene 
• 674303-51-6 (1S,8R)-2,6-diazatricyclo[6.2.1.0^2,7]undec-6-ene 
• 664341-72-4 (1S,4R)-1-tert-butoxycarbonylamino-4-hydroxymethylcyclopentane 
• 117957-62-7 (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentanone 
• 859147-57-2 N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 859147-53-8 N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine 
• 859147-55-0 N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-2',3'-O-isopropylideneadenosine 
• 859147-59-4 N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine 
• 674303-45-8 (1R,4S)-3-{(3S)-3-azido-3-phenylpropyl}-3-azabicyclo[2.2.1]heptan-2-one 
• 71830-07-4 (1S,3R)-3-aminocyclopentanecarboxylic acid 

Relevant articles and documents

Synthesis and evaluation of cyclopentane-based muraymycin analogs targeting MraY

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Identification and application of enantiocomplementary lactamases for Vince lactam derivatives

Four enzymes showing hydrolytic activity on derivatives of 2-azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) were successfully identified through analysis of protein crystal structure and amino acid sequence alignments. Enantiocomplementary activities were observed on Vince lactam and its saturated analog 2-azabicyclo[2.2.1]heptan-3-one with non-heme chloroperoxidase (CPO-T) from Streptomyces aureofaciens, cyclic imide hydrolase (CIH) from Pseudomonas putida, polyamidase (NfpolyA) from Nocardia farcinica, and amidase (AMI) from Rhodococcus globerulus, and perfect kinetic resolution was achieved (E>200). Computational analysis of amide bond resonance stabilization in lactams correlated well with the overall reactivity pattern of the lactams as a function of ring size and strain. The biocatalysts cloned and investigated in this study could be of interest for the synthesis of enantiopure carbocyclic nucleoside analogues.