| Identification | Back Directory | [Name]
8-Methylquinoline N-oxide | [CAS]
4053-38-7 | [Synonyms]
8-Methylquinoline N-oxide
8-methylquinoline 1-oxide
Quinoline, 8-methyl-, 1-oxide | [Molecular Formula]
C10H9NO | [MDL Number]
MFCD22666433 | [MOL File]
4053-38-7.mol | [Molecular Weight]
159.18 |
| Chemical Properties | Back Directory | [Melting point ]
240-260°C | [Boiling point ]
315.0±35.0 °C(Predicted) | [density ]
1.10±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
solid | [pka]
1.08±0.30(Predicted) | [InChI]
1S/C10H9NO/c1-8-4-2-5-9-6-3-7-11(12)10(8)9/h2-7H,1H3 | [InChIKey]
PIOGDSHYODXWAK-UHFFFAOYSA-N | [SMILES]
[O-][N+]1=CC=CC2=C1C(C)=CC=C2 |
| Hazard Information | Back Directory | [Reactions]
A Pd(II)-catalyzed regioselective dual C(sp3)–H/C7(sp2)–H activation and annulation of 8-methylquinoline N-oxides with maleimide has been accomplished[1]. The use of N-oxide as a weak directing group under Pd(II)-complex catalysis activates the initial C(sp3)–H and triggers a relayed, second C7(sp2)–H activation. The dual C–H bond activation, [3 + 2]-annulation, facile introduction and removal of the directing group, substrate scope, and functional group diversity are the important practical features.
 | [References]
[1] Dual C(sp3)–H and C(sp2)–H Activation of 8-Methylquinoline N-Oxides: A Route to Access C7–H Bond. DOI:10.1021/acs.orglett.4c02584
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