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[ CAS No. 548-19-6 ]

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Chemical Structure| 548-19-6
Chemical Structure| 548-19-6
Structure of 548-19-6 * Storage: {[proInfo.prStorage]}

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Alternatived Products of [ 548-19-6 ]

Product Details of [ 548-19-6 ]

CAS No. :548-19-6 MDL No. :MFCD00597035
Formula : C32H22O10 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :566.51 g/mol Pubchem ID :5318569
Synonyms :

1. Isoginkgetin

Safety of [ 548-19-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 548-19-6 ]

  • Downstream synthetic route of [ 548-19-6 ]

[ 548-19-6 ] Synthesis Path-Downstream   1~16

YieldReaction ConditionsOperation in experiment
Oxydation mit H2O2 in wss. KOH;
Methylierung;
Entmethylierung;
Aethylierung;
Acetylierung;

  • 2
  • [ 7722-84-1 ]
  • [ 548-19-6 ]
  • [ 2206-43-1 ]
  • [ 100-09-4 ]
  • 3
  • [ 548-19-6 ]
  • [ 74-88-4 ]
  • [ 22783-08-0 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 20℃;
  • 4
  • [ 548-19-6 ]
  • [ 74-88-4 ]
  • [ 78511-92-9 ]
YieldReaction ConditionsOperation in experiment
94% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Treatment of isoginkgetin with a large excess of methyl iodide (5 equiv) under basic conditions furnished fully methylated compound 11 [cf. Scheme 2 (Fig. 6)] . The use of 3 equivalents of Mel produced a mixture of trialkylated products 9 and 10 which were easily separated by column chromatography. Reaction of isoginkgetin with pyridinium chloride allows ether cleavage and afforded the polyphenolic compound 12. Scheme 2 (cf. Figure 6):
  • 5
  • [ 548-19-6 ]
  • [ 74-88-4 ]
  • 5,7,4′,7″,4″′-pentamethylamentoflavone [ No CAS ]
  • C35H28O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Treatment of isoginkgetin with a large excess of methyl iodide (5 equiv) under basic conditions furnished fully methylated compound 11 [cf. Scheme 2 (Fig. 6)] . The use of 3 equivalents of Mel produced a mixture of trialkylated products 9 and 10 which were easily separated by column chromatography. Reaction of isoginkgetin with pyridinium chloride allows ether cleavage and afforded the polyphenolic compound 12. Scheme 2 (cf. Figure 6):
  • 6
  • [ 548-19-6 ]
  • [ 1617-53-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine hydrochloride; at 180℃; Treatment of isoginkgetin with a large excess of methyl iodide (5 equiv) under basic conditions furnished fully methylated compound 11 [cf. Scheme 2 (Fig. 6)] . The use of 3 equivalents of Mel produced a mixture of trialkylated products 9 and 10 which were easily separated by column chromatography. Reaction of isoginkgetin with pyridinium chloride allows ether cleavage and afforded the polyphenolic compound 12. Scheme 2 (cf. Figure 6):
  • 7
  • [ 548-19-6 ]
  • C32H18O16P2(6-)*6Na(1+) [ No CAS ]
  • C32H20O16P2(4-)*4Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; tetrabutylammomium bromide / water; dichloromethane / 2 h / 20 °C 2: trimethylsilyl iodide / dichloromethane / 20 °C
  • 8
  • [ 548-19-6 ]
  • [ 814-49-3 ]
  • 8-(5-(7-((diethoxyphosphoryl)oxy)-5-hydroxy-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl)-5-hydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl diethyl phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: isoginkgetin With potassium hydroxide In water monomer at 20℃; for 0.25h; Inert atmosphere; Stage #2: diethyl chlorophosphate With tetrabutylammonium bromide In dichloromethane; water monomer at 20℃; for 2h;
With tetrabutylammonium bromide; potassium hydroxide In dichloromethane; water monomer at 20℃; for 2h; The synthesis of IP2 compounds (2 and 2'), depicted in Scheme 1 (Fig. 5), was accomplished from isoginkgetin by phosphorylation employing in situ formation of diethylchlorophosphite to provide 1. Further cleavage of the ethyl ester protective groups with iodotrimethylsilane afforded the phosphoric acid intermediate, which was immediately treated with sodium hydroxide to complete a practical route to the disodium phosphate prodrugs 2 and 2'. The water solubility of 2 and 2' was found to be considerably higher than that of the parent compound isoginkgetin.
  • 9
  • 5,7-bis(benzyloxy)-8-iodo-2-(4-methoxyphenyl)-4H-chromen-4-one [ No CAS ]
  • [ 548-19-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation 2: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C
  • 10
  • (E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(3-iodo-4-methoxyphenyl)prop-2-en-1-one [ No CAS ]
  • [ 548-19-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: iodine / dimethyl sulfoxide / 16 h / 100 °C / Inert atmosphere 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere; Sealed tube 3: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation 4: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C
  • 11
  • 5,7-bis(benzyloxy)-2-(3-iodo-4-methoxyphenyl)-4H-chromen-4-one [ No CAS ]
  • [ 548-19-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere; Sealed tube 2: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation 3: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C
  • 12
  • 5,7-bis(benzyloxy)-2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-chromen-4-one [ No CAS ]
  • [ 548-19-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation 2: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C
  • 13
  • 5,7-bis(benzyloxy)-8-(5-(5,7-bis(benzyloxy)-4-oxo-4H-chromen-2-yl)-2-methoxyphenyl)-2-(4-methoxyphenyl)-4H-chromen-4-one [ No CAS ]
  • [ 548-19-6 ]
YieldReaction ConditionsOperation in experiment
75% With palladium 10% on activated carbon; palladium hydroxide on carbon; hydrogen In methanol; dichloromethane at 20℃; for 5h;
  • 14
  • [ 548-19-6 ]
  • C32H21O13P(2-)*2Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / water monomer / 0.25 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: trimethylsilyl bromide / dichloromethane / 16 h / 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C 3.1: formic acid / water monomer; acetonitrile
  • 15
  • [ 548-19-6 ]
  • sodium 5-hydroxy-8-(5-(5-hydroxy-4-oxo-7-(phosphonatooxy)-4H-chromen-2-yl)-2-methoxyphenyl)-2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / water monomer / 0.25 h / 20 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: trimethylsilyl bromide / dichloromethane / 16 h / 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C
  • 16
  • [ 108-73-6 ]
  • [ 548-19-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dmap / 0.33 h / 20 - 200 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 20 - 50 °C / Inert atmosphere 3: iodine; trifluoromethane sulfonic acid silver salt / dichloromethane / 0 °C / Inert atmosphere 4: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation 5: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C
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