7-hydroxyflavone
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 80℃; for 24h; | 98% |
With dipotassium peroxodisulfate; alkaline solution Erwaermen des Reaktionsprodukts mit wss. Salzsaeure; | |
Multi-step reaction with 2 steps 1: aluminium chloride / 160 °C 2: aq. NaOH solution; aqueous hydrogen peroxide View Scheme | |
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction; |
C29H22O4
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 40℃; under 4560.31 - 6080.41 Torr; | 90.5% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol at 20℃; for 3h; | 83% |
C29H18O6
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With sodium methylate In ethanol; dichloromethane | 63% |
With water; sodium hydroxide In 1,4-dioxane; methanol at 20℃; |
8-acetyl-7-hydroxy-2-phenyl-chromen-4-one
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide |
1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With sodium acetate; acetic acid Erwaermen des Reaktionsprodukts mit methanol. Kalilauge; |
Conditions | Yield |
---|---|
With diphenylether |
1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione
sodium acetate
acetic acid
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
anschliessend Erhitzen mit wss.-methanol. Kalilauge; |
2-hydroxyresorcinol
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With aluminium trichloride; nitrobenzene Behandeln der Reaktionsloesung mit Phenylpropioloylchlorid und Benzol; | |
Multi-step reaction with 6 steps 1: boron trifluoride diethyl etherate / 50 - 100 °C / Inert atmosphere; Large scale 2: potassium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 6 h / 90 - 110 °C / Inert atmosphere; Large scale 3: hydrogenchloride; acetic acid / water / 3 h / 20 °C 4: potassium hydroxide / water; ethanol / 20 - 30 °C 5: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere 6: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr View Scheme |
1-Phenyl-3-(2,3,4-trihydroxy-phenyl)-propane-1,3-dione
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With sulfuric acid In acetic acid at 95 - 100℃; Yield given; |
benzoic acid anhydride
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With sodium benzoate at 180 - 185℃; Kochen des Reaktionsprodukts mit waessrig-alkoholischer Kalilauge; |
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With hydrogen iodide |
7-hydroxyflavone
A
7,8-dihydroxyflavone
2',3',4'-trihydroxyacetophenone
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) lithium bis(trimethyl)silyl amide (LiHMDS) / 1) THF, a) -78 deg C, b) -10 deg C, 2) THF, a) -78 deg C, b) room temp. 2: H2SO4 / acetic acid / 95 - 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 120 - 140 °C 2: water; sodium hydroxide / 1,4-dioxane; methanol / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 8 h / 50 °C 2.1: trifluoroacetic acid / toluene / 2 h / 20 °C 3.1: potassium hydroxide / ethanol; water / 36 h / 20 °C 3.2: pH Ca. 5 / Cooling with ice 4.1: iodine; dimethyl sulfoxide / 12 h / 110 °C 5.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: potassium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / 6 h / 90 - 110 °C / Inert atmosphere; Large scale 2: hydrogenchloride; acetic acid / water / 3 h / 20 °C 3: potassium hydroxide / water; ethanol / 20 - 30 °C 4: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere 5: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1) lithium bis(trimethyl)silyl amide (LiHMDS) / 1) THF, a) -78 deg C, b) -10 deg C, 2) THF, a) -78 deg C, b) room temp. 2: H2SO4 / acetic acid / 95 - 100 °C View Scheme |
4-oxo-2-phenyl-4H-chromen-7-yl acetate
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminium chloride / 60 °C 2: aq. NaOH solution; aqueous hydrogen peroxide View Scheme |
C29H24O4
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: iodine; dimethyl sulfoxide / 12 h / 110 °C 2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme |
1-(2,3,4-tris(benzyloxy)phenyl)ethanone
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid / toluene / 2 h / 20 °C 2.1: potassium hydroxide / ethanol; water / 36 h / 20 °C 2.2: pH Ca. 5 / Cooling with ice 3.1: iodine; dimethyl sulfoxide / 12 h / 110 °C 4.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: hydrogenchloride; acetic acid / water / 3 h / 20 °C 2: potassium hydroxide / water; ethanol / 20 - 30 °C 3: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere 4: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr View Scheme |
1-(3,4-bis(benzyloxy)-2-hydroxyphenyl)ethanone
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium hydroxide / ethanol; water / 36 h / 20 °C 1.2: pH Ca. 5 / Cooling with ice 2.1: iodine; dimethyl sulfoxide / 12 h / 110 °C 3.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium hydroxide / water; ethanol / 20 - 30 °C 2: iodine / dimethyl sulfoxide / 7 h / 110 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol; tetrahydrofuran / 40 °C / 4560.31 - 6080.41 Torr View Scheme |
Conditions | Yield |
---|---|
Stage #1: 2',3',4'-trihydroxyacetophenone; benzoyl chloride With pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene for 8h; Reflux; Stage #2: With sodium hydroxide In 1,4-dioxane; methanol | |
Stage #1: 2',3',4'-trihydroxyacetophenone; benzoyl chloride With potassium carbonate In acetone for 12.1667h; Baker-Venkataraman Rearrangement; Inert atmosphere; Reflux; Stage #2: In methanol; water for 3h; Inert atmosphere; Reflux; |
2'-hydroxy-3',4'-dimethoxyacetophenone
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: pyridine / 1 h / 75 °C 2.1: pyridine; potassium hydroxide / 2 h / 50 - 75 °C 3.1: acetic acid; sulfuric acid / 1 h / 90 - 110 °C 3.2: 0.5 h / 0 - 20 °C 4.1: boron tribromide / dichloromethane / Heating View Scheme |
7,8-dimethoxyflavone
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane Heating; |
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridine; potassium hydroxide / 2 h / 50 - 75 °C 2.1: acetic acid; sulfuric acid / 1 h / 90 - 110 °C 2.2: 0.5 h / 0 - 20 °C 3.1: boron tribromide / dichloromethane / Heating View Scheme |
1-(2-hydroxy-3,4-dimethoxy-phenyl)-3-phenyl-propane-1,3-dione
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: acetic acid; sulfuric acid / 1 h / 90 - 110 °C 1.2: 0.5 h / 0 - 20 °C 2.1: boron tribromide / dichloromethane / Heating View Scheme |
7-hydroxyflavone
A
7,4'-Dihydroxyflavon
B
6,7-dihydroxyflavone
C
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction; |
FLAVONE
A
7,4'-Dihydroxyflavon
B
6,7-dihydroxyflavone
C
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: cytochromes P450 in human liver microsomes / Enzymatic reaction 2: cytochromes P450 in human liver microsomes / Enzymatic reaction View Scheme |
FLAVONE
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: cytochromes P450 in human liver microsomes / Enzymatic reaction 2: cytochromes P450 in human liver microsomes / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 2h; | 94% |
With potassium carbonate In acetone at 60℃; |
7,8-dihydroxyflavone
allyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Inert atmosphere; Reflux; | 78% |
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With Lawessons reagent In toluene at 40℃; for 0.5h; Substitution; | 77% |
trifluoromethylsulfonic anhydride
7,8-dihydroxyflavone
4-oxo-2-phenyl-4H-chromene-7,8-diyl Bis(trifluoromethanesulfonate)
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -78 - 0℃; Inert atmosphere; | 76% |
Stage #1: 7,8-dihydroxyflavone With pyridine In dichloromethane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at -78 - 0℃; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
With tetraethoxy orthosilicate In acetonitrile at 20℃; for 24h; Inert atmosphere; | 70% |
3-chloro-3-methylbut-1-yne
7,8-dihydroxyflavone
1,8-diazabicyclo[5.4.0]undec-7-ene
7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-4H-chromen-4-one
Conditions | Yield |
---|---|
With CuCl2 In acetonitrile | 69% |
3-chloro-3-methylbut-1-yne
7,8-dihydroxyflavone
7,8-bis-(1,1-dimethyl-prop-2-ynyloxy)-2-phenyl-4H-chromen-4-one
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper dichloride In acetonitrile at 0 - 20℃; | 69% |
With copper(l) iodide; potassium carbonate; potassium iodide In acetone at 50℃; for 4h; | 62% |
7,8-dihydroxyflavone
ethylenediamine
Conditions | Yield |
---|---|
In ethanol at 100℃; | 56% |
7,8-dihydroxyflavone
acetic anhydride
4-oxo-2-phenyl-4H-chromene-7,8-diyl diacetate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 53.3% |
With potassium carbonate In dichloromethane at 20℃; | 53.3% |
With sodium acetate |
7,8-dihydroxyflavone
2,3-dibromopropionic acid ethyl ester
A
7,8-<3-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
B
7,8-<2-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 20h; Heating; | A 8% B 44% |
7,8-dihydroxyflavone
2,3-dibromopropionic acid ethyl ester
A
7,8-<3-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
B
7,8-<2-(Ethoxycarbonyl)-ethylenedioxy>-2-phenyl-4H-1-benzopyran-4-one
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 20h; Heating; | A 8% B 44% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In pyridine for 24h; Cooling with ice; | 25% |
7,8-dihydroxyflavone
isopentanoyl chloride
4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(3-methylbutanoate)
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 23.1% |
With potassium carbonate In dichloromethane at 20℃; | 23.1% |
7,8-dihydroxyflavone
ethyl isocyanate
4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(ethylcarbamate)
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 22.5% |
With potassium carbonate In dichloromethane at 20℃; | 22.5% |
coniferal alcohol
7,8-dihydroxyflavone
Conditions | Yield |
---|---|
With silver carbonate In acetone; benzene at 60℃; for 24h; | 21% |
7,8-dihydroxyflavone
pivaloyl chloride
4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(2,2-dimethylpropanoate)
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 20.9% |
With potassium carbonate In dichloromethane at 20℃; | 20.9% |
1-methyl-piperazine
bis(trichloromethyl) carbonate
7,8-dihydroxyflavone
4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(4-methylpiperazine-1-carboxylate).
Conditions | Yield |
---|---|
Stage #1: 1-methyl-piperazine; bis(trichloromethyl) carbonate In tetrahydrofuran at -78℃; for 1h; Stage #2: 7,8-dihydroxyflavone In pyridine; water; acetone at 0 - 20℃; | 20.2% |
7,8-dihydroxyflavone
propionyl chloride
4-oxo-2-phenyl-4H-chromene-7,8-diyl dipropionate
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 17.4% |
With potassium carbonate In dichloromethane at 20℃; | 17.4% |
7,8-dihydroxyflavone
N,N-Dimethylcarbamoyl chloride
4-oxo-2-phenyl-4H-chromene-7,8-diyl bis(dimethylcarbamate)
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 15.9% |
With potassium carbonate In dichloromethane at 20℃; | 15.9% |
7,8-dihydroxyflavone
chloroformic acid ethyl ester
diethyl (4-oxo-2-phenyl-4H-chromene-7,8-diyl) bis(carbonate)
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane at 20℃; | 15.9% |
With potassium carbonate In dichloromethane at 20℃; | 15.9% |
diazomethane
7,8-dihydroxyflavone
7,8-dimethoxyflavone
Conditions | Yield |
---|---|
With diethyl ether |
[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide
7,8-dihydroxyflavone
8-phenyl-[1,3]dioxolo[4,5-h]chromen-6-one
Conditions | Yield |
---|---|
With potassium carbonate; acetone |
Conditions | Yield |
---|---|
With potassium carbonate; acetone | |
With alkaline solution |
The 4H-1-Benzopyran-4-one,7,8-dihydroxy-2-phenyl-, with CAS registry number 38183-03-8, belongs to the following product categories: (1)Di-substituted Flavones; (2)Biochemistry; (3)Flavonoids. It has the systematic name of 7,8-dihydroxy-2-phenyl-4H-chromen-4-one. Its classification code is Mutation data. When use this chemical, avoid contact with skin and eyes. What's more, its EINECS is 253-812-4.
Physical properties of 4H-1-Benzopyran-4-one,7,8-dihydroxy-2-phenyl-: (1)ACD/LogP: 2.51; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.49; (4)ACD/LogD (pH 7.4): 1.82; (5)ACD/BCF (pH 5.5): 45.16; (6)ACD/BCF (pH 7.4): 9.82; (7)ACD/KOC (pH 5.5): 525.11; (8)ACD/KOC (pH 7.4): 114.21; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.698; (14)Molar Refractivity: 67.97 cm3; (15)Molar Volume: 176.1 cm3; (16)Polarizability: 26.94×10-24cm3; (17)Surface Tension: 68.2 dyne/cm; (18)Density: 1.443 g/cm3; (19)Flash Point: 193.5 °C; (20)Enthalpy of Vaporization: 79.07 kJ/mol; (21)Boiling Point: 494.4 °C at 760 mmHg; (22)Vapour Pressure: 2.13E-10 mmHg at 25°C.
Preparation: this chemical can be prepared by C29H18O6. This reaction will need reagent NaOMe and solvents ethanol, CH2Cl2. The yield is about 63%.
Uses of 4H-1-Benzopyran-4-one,7,8-dihydroxy-2-phenyl-: it can be used to produce 7,8-dihydroxy-2-phenyl-chromene-4-thione. This reaction will need reagent Lawesson's reagent and solvent toluene. The reaction time is 30 min with reaction temperature of 40 ℃. The yield is about 77%.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C\1c3c(O/C(=C/1)c2ccccc2)c(O)c(O)cc3
(2)InChI: InChI=1/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
(3)InChIKey: COCYGNDCWFKTMF-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
(5)Std. InChIKey: COCYGNDCWFKTMF-UHFFFAOYSA-N
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