758272
8-Ethylquinoline N-oxide
97%
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About This Item
Empirical Formula (Hill Notation):
C11H11NO
Molecular Weight:
173.21
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Product Name
8-Ethylquinoline N-oxide, 97%
InChI
1S/C11H11NO/c1-2-9-5-3-6-10-7-4-8-12(13)11(9)10/h3-8H,2H2,1H3
SMILES string
CCC1=CC=CC2=C1[N+]([O-])=CC=C2
InChI key
LZEBWZDDNNWJJK-UHFFFAOYSA-N
assay
97%
form
solid
reaction suitability
reagent type: oxidant
mp
104-109 °C
storage temp.
2-8°C
Application
Reactant for the preparation of:
- α, β-unsaturated enones with catalytic amounts of Gold complexes
- Synthesis of azetidines (4-membered nitrogen containing heterocycles) through an intramolecular oxidative cyclization in the presence of catalytic amounts of Gold complexes
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes.
Longwu Ye et al.
Angewandte Chemie (International ed. in English), 50(14), 3236-3239 (2011-03-08)
Biao Lu et al.
Journal of the American Chemical Society, 132(40), 14070-14072 (2010-09-22)
Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A
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