Furaneol → 4-bromo-5-(4-methoxyphenyl)-2(5H)-furanone

HRID 1045290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045290
BrC1C(=O)OC(O)C=1Br.[Br:10][C:11]1[C:15](OC)([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[O:14][C:13](=[O:26])[CH:12]=1.BrC1C(OC2C=CC(C([O-])=O)=CC=2)(C2C=CC(OC)=CC=2)OC(=O)C=1.[B-]1(O)(O)O[C@]2(O)[C@@H](O)CO[C@]2(C)O1.OC1C(=O)C(C)OC=1C.COC1(C2C=CC=CC=2)C(=O)C(C2C=CC=CC=2)=CO1.C(C1C(=O)CCC=1)CCCC>>[Br:10][C:11]1[CH:15]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[O:14][C:13](=[O:26])[CH:12]=1

Komponenten

8

Edukt 7

HCID 19309FuraneolHCID 935593,4-Dibromo-5-hydroxyfuran-2(5H)-oneHCID 1175492-Cyclopenten-1-one, 2-pentyl-HCID 1708742-Methoxy-2,4-diphenyl-3(2H)-furanoneHCID 446576Autoinducer 2HCID 42050384-Bromo-5-methoxy-5-(4-methoxyphenyl)furan-2(5H)-oneHCID 1317300324-{[3-Bromo-2-(4-methoxyphenyl)-5-oxo-2 5-dihydro-2-furanyl]oxy}benzoate

Produkt 1

HCID 40890754-bromo-5-(4-methoxyphenyl)-2(5H)-furanone

Versuchsvorschrift

3,4-dibromo-5-hydroxy-2(5H)-furanone (manufactured by SIGMA), Compound 3: 4-bromo-5-methoxy-5-(4-methoxyphenyl)-2(5H)-furanone (manufactured by SIGMA), and Compound 4: 4-{[3-bromo-2-(4-methoxyphenyl)-5-oxo-2,5-dihydro-2-furanyl]oxy}benzoate (manufactured by SIGMA) were used as test drugs. As positive controls, three (3) kinds of known compounds as an AI-2 inhibitory compounds, such as Compound 5: 4-hydroxy-2,5-dimethyl-3(2H)-furanone (manufactured by SIGMA), Compound 6: 2-methoxy-2,4-diphenyl-3(2H)-furanone (manufactured by SIGMA), and Compound 7: 2-pentyl-2-cyclopentene-1-one (manufactured by SIGMA) were used (see Bassseler et al., Bacteriol. 179, p. 4043-4045, 1997; Yoshida A. et al., Appl. Environ. Microbial., 71(5), p. 2372-2380, 2005; and Wen Z. T. et al., J. Bacteriol., 189(9), p. 2682-2691, 2004).

Quellen und Nachweise

ORD-Eintrag
ord-1d3da3c7a1e1413c936959ff83c23b48
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08568986B2

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