441279
(1R)-(−)-2-Azabicyclo[2.2.1]hept-5-en-3-one
≥98%
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About This Item
Empirical Formula (Hill Notation):
C6H7NO
CAS Number:
Molecular Weight:
109.13
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
418-530-1
Beilstein/REAXYS Number:
4230721
MDL number:
Assay:
≥98%
Form:
solid
InChI key
DDUFYKNOXPZZIW-UHNVWZDZSA-N
InChI
1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1
SMILES string
O=C1N[C@@H]2C[C@H]1C=C2
assay
≥98%
form
solid
optical activity
[α]20/D −565°, c = 1 in chloroform
optical purity
ee: 99% (HPLC)
mp
94-97 °C (lit.)
Quality Level
Related Categories
General description
(1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one is a bicyclic γ-lactam.
Application
(1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one can be used as a precursor to prepare:
- Amino-peramivir, a potent neuraminidase inhibitor.
- Five membered analogs of 4-amino-5-halopentanoic acids as potential GABA aminotransferase (GABA-AT) inactivators.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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A new class of conformationally rigid analogues of 4-amino-5-halopentanoic acids, potent inactivators of ?-aminobutyric acid aminotransferase.
Qiu J and Silverman RB.
Journal of Medicinal Chemistry, 43(4), 706-720 (2000)
2-Azabicyclo [2.2. 1] hept-5-en-3-one: chemical profile of a versatile synthetic building block and its impact on the development of therapeutics.
Singh R and Vince R.
Chemical Reviews, 112(8), 4642-4686 (2012)
The de-guanidinylated derivative of peramivir remains a potent inhibitor of influenza neuraminidase
Bromba CM, et al.
Bioorganic & medicinal chemistry letters, 21(23), 7137-7141 (2011)
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