Selenium Dioxide → 1,2-Naphthoquinone

HRID 719172

Reaktionsgleichung

Reaktionsgleichung von HRID 719172
[CH3:1][CH:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=2[O:3]1.[O:13]=[C:14]1[CH2:23][CH2:22][CH2:21][C:20]2[C:19]([C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=[CH:16][C:15]1=2.[Se](=O)=[O:29]>>[O:13]=[C:14]1[CH2:23][CH2:22][CH2:21][C:20]2[C:19]([C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=[CH:16][C:15]1=2.[C:8]1(=[O:12])[C:9]2[C:4](=[CH:1][CH:2]=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]1=[O:29].[CH3:27][O:26][C:24]([C:19]1[C:20]2[CH:21]=[CH:22][C:23](=[O:3])[C:14](=[O:13])[C:15]=2[CH:16]=[CH:17][CH:18]=1)=[O:25]

Komponenten

6

Edukt 3

HCID 24007Selenium DioxideHCID 115573412-Methyl-2,6,7,8-tetrahydro-chromen-5-oneHCID 12284900Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-1-carboxylate

Produkt 3

HCID 106671,2-NaphthoquinoneHCID 98131985,6-Dioxo-5,6-dihydro-naphthalene-1-carboxylic acid methyl esterHCID 12284900Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-1-carboxylate

Versuchsvorschrift

Methyl 5-oxo-5,6,7,8-tetrahydro-1-naphthoate was prepared according to the literature (J. Org. Chem. 1976, p2918) from 2-methyl-2,6,7,8-tetrahydro-chromen-5-one (Tetrahedron Letters, 1975, p3407). Treatment of methyl 5-oxo-5,6,7,8-tetrahydro-1-naphthoate with selenium dioxide as described in Reference Example 1A yielded the corresponding 1,2-naphthoquinone, 5,6-dioxo-5,6-dihydro-naphthalene-1-carboxylic acid methyl ester, which was coupled with 2,3-diamino-benzoic acid, diacetate salt, as described in Reference Example 1A to yield the title compound.

Quellen und Nachweise

ORD-Eintrag
ord-f9a514ff147742fc9893084408fcf88e
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132419B2

Verknüpfte Notizen

Wird geladen…