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Merck
CN

331910

2-Azabicyclo[2.2.1]hept-5-en-3-one

98%

Synonym(s):

(±)-2-Azabicyclo[2.2.1]hept-5-en-3-one, 4-Amino-2-cyclopentene-1-carboxylic acid lactam

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About This Item

Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
49805-30-3
Molecular Weight:
109.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24860009
MDL number:
MFCD00213364
Beilstein/REAXYS Number:
508342
Assay:
98%

Key Documents

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Product Name

2-Azabicyclo[2.2.1]hept-5-en-3-one, 98%

InChI

1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1

SMILES string

O=C1N[C@H]2C[C@@H]1C=C2

InChI key

DDUFYKNOXPZZIW-CRCLSJGQSA-N

assay

98%

bp

102-106 °C/0.25 mmHg (lit.)

mp

54-58 °C (lit.)

Quality Level

100

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Application

2-Azabicyclo[2.2.1]hept-5-en-3-one was used in:
  • preparation of (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine, a precursor of analog of bredinin
  • synthesis of therapeutic drugs
  • chemoenzymatic synthesis of (−)-carbovir

General description

2-Azabicyclo[2.2.1]hept-5-en-3-one is also referred as vince lactam. It is a versatile intermediate in the synthesis of carbocyclic nucleosides. 2-Azabicyclo[2.2.1]hept-5-en-3-one and its monohydrated complex was investigated in a supersonic jet by Fourier transform microwave spectroscopy.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBB3668V
BCBB3668
05109ED
07419MZ
03903TY

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Chemoenzymatic synthesis of (-)-carbovir utilizing a whole cell catalysed resolution of 2-azabicyclo [2.2. 1] hept-5-en-3-one.
Steven, J. C.
Journal of the Chemical Society. Chemical Communications, 16, 1120-1121 (1990)
Patricia Écija et al.
The journal of physical chemistry. A, 116(41), 10099-10106 (2012-09-19)
2-Azabicyclo[2.2.1]hept-5-en-3-one (ABH or Vince lactam) and its monohydrated complex (ABH···H(2)O) have been observed in a supersonic jet by Fourier transform microwave spectroscopy. ABH is broadly used in the synthesis of therapeutic drugs, whereas the ABH···H(2)O system offers a simple model
Vasu Nair et al.
Molecules (Basel, Switzerland), 18(9), 11576-11585 (2013-09-21)
The natural nucleoside antibiotic, bredinin, exhibits antiviral and other biological activities. While various nucleosides related to bredinin have been synthesized, its carbocyclic analog has remained unknown. Synthesis of this heretofore unknown analog of bredinin is described. The key precursor, (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

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