Product Name

  • Name

    8-ACETYL DIMETHOXYCOUMARIN

  • EINECS 223-541-6
  • CAS No. 3949-36-8
  • Article Data56
  • CAS DataBase
  • Density 1.286 g/cm3
  • Solubility
  • Melting Point 119-122 °C(lit.)
  • Formula C11H8O3
  • Boiling Point 391.6 °C at 760 mmHg
  • Molecular Weight 188.183
  • Flash Point 179 °C
  • Transport Information
  • Appearance yellow crystalline powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3949-36-8 (8-ACETYL DIMETHOXYCOUMARIN)
  • Hazard Symbols IrritantXi
  • Synonyms Coumarin,3-acetyl- (6CI,7CI,8CI);3-Acetyl-2H-1-benzopyran-2-one;3-Acetylbenzopyran-2-one;3-Acetylcoumarin;NSC 31678;
  • PSA 47.28000
  • LogP 1.99560

Synthetic route

salicylaldehyde
90-02-8

salicylaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

ethyl acetoacetate
141-97-9

ethyl acetoacetate

salicylaldehyde
90-02-8

salicylaldehyde

A

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

B

ethyl 2-(2-hydroxybenzylidene)-3-oxobutanoate
62558-68-3

ethyl 2-(2-hydroxybenzylidene)-3-oxobutanoate

Conditions
ConditionsYield
With methyl aminopropyl grafted mesoporous silica SBA-15 In neat (no solvent) at 49.84℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Knoevenagel Condensation;A 100%
B n/a
2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

ethyl acetoacetate
141-97-9

ethyl acetoacetate

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With piperidine at 20℃; for 0.0833333h; Knoevenagel condensation;99%
With ethylenediamine diacetic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; Knoevenagel condensation;92%
With 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl) In ethanol at 60℃; for 3h;90%
O-Merrifield resin-bound 4-(2\-acetoacetylethyl)phenol

O-Merrifield resin-bound 4-(2\-acetoacetylethyl)phenol

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With piperidine In ethanol for 2h; Knoevenagel condensation; Heating;99%
Phosphoric acid dimethyl ester 1-(2-oxo-2H-chromen-3-yl)-vinyl ester
219506-41-9

Phosphoric acid dimethyl ester 1-(2-oxo-2H-chromen-3-yl)-vinyl ester

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating;90%
salicylaldehyde
90-02-8

salicylaldehyde

N-phenylacetoacetamide
102-01-2

N-phenylacetoacetamide

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃; for 3h;90%
salicylaldehyde
90-02-8

salicylaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With tert.-butylhydroperoxide; diphenylether; Fe3O(biphenyl-4,4'-dicarboxylate)3 In water; N,N-dimethyl-formamide at 60℃; for 3h; Reagent/catalyst;89%
With L-lysine In water at 60℃; for 6h; Knoevenagel condensation;88%
With thiourea S,S-dioxide at 80℃; for 4h;86%
salicylaldehyde
90-02-8

salicylaldehyde

methyl(ethyl) acetoacetate

methyl(ethyl) acetoacetate

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With piperidine In neat (no solvent) at 20℃; Knoevenagel Condensation;89%
coumarin
91-64-5

coumarin

acetaldehyde
75-07-0

acetaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With dipotassium peroxodisulfate; methyl tri-n-octyl ammonium hydrogen sulfate In chlorobenzene at 100℃; for 8h; Sealed tube; regioselective reaction;88%
3-acetyl-4-chlorocoumarin

3-acetyl-4-chlorocoumarin

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; isopropyl alcohol at 90℃; for 12h; Green chemistry; regioselective reaction;85%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With titanium(IV) isopropylate In dichloromethane at 25℃; Knoevenagel reaction;76%
salicylaldehyde
90-02-8

salicylaldehyde

poly(styrene-co-allyl) ethyl 3-oxobutanoate derivative

poly(styrene-co-allyl) ethyl 3-oxobutanoate derivative

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With piperidine; acetic acid In ethanol for 4h; Heating;70%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

salicylaldehyde
90-02-8

salicylaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
Stage #1: 4-methyleneoxetan-2-one With titanium(IV) isopropylate In isopropyl alcohol at 0℃; for 3h; Knoevenagel condensation; Inert atmosphere;
Stage #2: salicylaldehyde In isopropyl alcohol at 22 - 25℃; Inert atmosphere;
59%
With potassium acetate
With triethylamine; toluene unter Entfernen des entstehenden Wassers;
ethyl acetoacetate
141-97-9

ethyl acetoacetate

salicylaldehyde
90-02-8

salicylaldehyde

A

ethyl 2-hydroxy-2-methyl-2H-chromene-3-carboxylate

ethyl 2-hydroxy-2-methyl-2H-chromene-3-carboxylate

B

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With alkaline protease from Bacillus licheniformis 2709 In water; dimethyl sulfoxide at 55℃; for 48h; Knoevenagel/intramolecular transesterification reaction; Enzymatic reaction; chemoselective reaction;A n/a
B 58%
3-bromoacetylcoumarin
29310-88-1

3-bromoacetylcoumarin

Cu(1+)*CF3(1-)*C6H15N*3FH

Cu(1+)*CF3(1-)*C6H15N*3FH

A

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

B

3-(3,3,3-trifluoropropanoyl)-2H-chromen-2-one
1400907-13-2

3-(3,3,3-trifluoropropanoyl)-2H-chromen-2-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 0.25h; Inert atmosphere;A 5%
B 57%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With potassium fluoride at 80℃; for 5h; Inert atmosphere;55%
acetyl chloride
75-36-5

acetyl chloride

3-<1-(Acetylhydrazono)ethyl>coumarin

3-<1-(Acetylhydrazono)ethyl>coumarin

A

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

B

3-(1-Triacetylhydrazinoethenyl)coumarin

3-(1-Triacetylhydrazinoethenyl)coumarin

Conditions
ConditionsYield
With N,N-dimethyl-aniline for 22h; Ambient temperature;A 53%
B 27%
3-acetyl-3,4-dihydrochromen-2-one
7391-56-2

3-acetyl-3,4-dihydrochromen-2-one

A

3,3'-diacetyl-3,3',4,4'-tetrahydro-4,4'-biscoumarin
59743-94-1

3,3'-diacetyl-3,3',4,4'-tetrahydro-4,4'-biscoumarin

B

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
In isopropyl alcohol Product distribution; Mechanism; Irradiation; air-saturated solvent; influence of other solvents of the product composition;A 50%
B 30%
In isopropyl alcohol Irradiation;A 50%
B 30%
4,4-bis(ethylsulfanyl)but-3-en-2-one
81375-98-6

4,4-bis(ethylsulfanyl)but-3-en-2-one

salicylaldehyde
90-02-8

salicylaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With copper(ll) bromide In acetonitrile at 20℃; for 6h;50%
(3-acetyl-2-oxo-chroman-4-yl)-phosphonic acid dimethyl ester
256504-29-7

(3-acetyl-2-oxo-chroman-4-yl)-phosphonic acid dimethyl ester

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
under 8 Torr; for 30h; Elimination; Thermolysis;48%
ethyl aminocrotonate
626-34-6, 7318-00-5, 41867-20-3

ethyl aminocrotonate

salicylaldehyde
90-02-8

salicylaldehyde

A

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

B

7-methyl<1>benzopyrano<4,3-d><1>benzoxacino<4,3-b>pyridine-6,16-dione
77117-11-4

7-methyl<1>benzopyrano<4,3-d><1>benzoxacino<4,3-b>pyridine-6,16-dione

Conditions
ConditionsYield
acetic acid In ethanol for 6h; Heating;A 45%
B 15%
3-bromoacetylcoumarin
29310-88-1

3-bromoacetylcoumarin

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With water; triphenylantimony at 120℃; for 0.166667h; Microwave irradiation;45%
With 2-chlorothiphenol In acetone for 5h; Reagent/catalyst; Reflux; chemoselective reaction;100 %Spectr.
salicylaldehyde
90-02-8

salicylaldehyde

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

A

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

(SR)-methyl 4-((RS)-1-methoxy-1,3-dioxobutan-2-yl)-2-methyl-4H-chromene-3-carboxylate

(SR)-methyl 4-((RS)-1-methoxy-1,3-dioxobutan-2-yl)-2-methyl-4H-chromene-3-carboxylate

(SR)-methyl 4-((SR)-1-methoxy-1,3-dioxobutan-2-yl)-2-methyl-4H-chromene-3-carboxylate

(SR)-methyl 4-((SR)-1-methoxy-1,3-dioxobutan-2-yl)-2-methyl-4H-chromene-3-carboxylate

Conditions
ConditionsYield
With bovine tendon hydrolysate In neat (no solvent) at 55℃; for 72h; Reagent/catalyst; Green chemistry;A 41%
B n/a
C n/a
With bovine tendon hydrolysate In neat (no solvent) at 55℃; for 29h; Temperature; Reagent/catalyst; Green chemistry;A 23%
B 38%
C n/a
piperidine
110-89-4

piperidine

ethyl acetoacetate
141-97-9

ethyl acetoacetate

salicylaldehyde
90-02-8

salicylaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

acetic anhydride
108-24-7

acetic anhydride

ethyl acetoacetate
141-97-9

ethyl acetoacetate

salicylaldehyde
90-02-8

salicylaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

ethyl acetoacetate
141-97-9

ethyl acetoacetate

salicylaldehyde
90-02-8

salicylaldehyde

A

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

B

7-methyl<1>benzopyrano<4,3-d><1>benzoxacino<4,3-b>pyridine-6,16-dione
77117-11-4

7-methyl<1>benzopyrano<4,3-d><1>benzoxacino<4,3-b>pyridine-6,16-dione

Conditions
ConditionsYield
With ammonia; acetic acid In ethanol for 6h; Heating; Yield given;
hydroxy-2 methyl-2 carbomethoxy-3 2H-cromene
85063-47-4

hydroxy-2 methyl-2 carbomethoxy-3 2H-cromene

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With water In pyridine Heating;
perchlorate de carbomethoxy-3 methyl-2 benzopyrilium

perchlorate de carbomethoxy-3 methyl-2 benzopyrilium

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
With water In pyridine for 4h; Heating; Yield given;
trisdimethylamino 2-acetyl (3H)benzo[b](1H-3-oxo-pyran-1-yl)phosphorane
256504-08-2

trisdimethylamino 2-acetyl (3H)benzo[b](1H-3-oxo-pyran-1-yl)phosphorane

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Conditions
ConditionsYield
under 5 Torr; for 0.5h; Elimination; Thermolysis;
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

benzaldehyde
100-52-7

benzaldehyde

3-cinnamoyl-2H-chromen-2-one
140399-50-4, 76011-67-1

3-cinnamoyl-2H-chromen-2-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In chloroform for 7h; Heating;97%
With piperidine at 140℃; for 0.05h; Microwave irradiation;97%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

1-(3'-coumarinyl)-3-(4''-bromophenyl)-2-propen-1-one
107126-88-5

1-(3'-coumarinyl)-3-(4''-bromophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With ZnS/g-C3N4 nanocomposite In ethanol for 1h; Claisen-Schmidt Condensation; Reflux; Green chemistry;91%
With piperidine In ethanol Claisen-Schmidt Condensation; Reflux;75%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

1-(3'-coumarinyl)-3-(4''-dimethylaminophenyl)-2-propen-1-one
91527-77-4

1-(3'-coumarinyl)-3-(4''-dimethylaminophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In chloroform for 7h; Heating;97%
With piperidine at 45 - 50℃; for 0.5h;91%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

1-(3'-coumarinyl)-3-(4''-chlorophenyl)-2-propen-1-one
91527-67-2

1-(3'-coumarinyl)-3-(4''-chlorophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In ethanol for 6h; Reflux;85%
With piperidine at 140℃; for 0.025h; Microwave irradiation;77.1%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

1-(3'-coumarinyl)-3-(4"-hydroxyphenyl)-2-propen-1-one

1-(3'-coumarinyl)-3-(4"-hydroxyphenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine at 140℃; for 0.05h; Microwave irradiation;97.8%
With ZnS/g-C3N4 nanocomposite In ethanol for 1.5h; Claisen-Schmidt Condensation; Reflux; Green chemistry;88%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

1-(3'-coumarinyl)-3-(4''-nitrophenyl)-2-propen-1-one
140399-53-7, 95331-78-5

1-(3'-coumarinyl)-3-(4''-nitrophenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With ZnS/g-C3N4 nanocomposite In ethanol for 1h; Catalytic behavior; Reagent/catalyst; Solvent; Claisen-Schmidt Condensation; Reflux; Green chemistry;92%
With piperidine at 140℃; for 0.0166667h; Microwave irradiation;78.3%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

triethyl phosphite
122-52-1

triethyl phosphite

C18H27O6PSi
1206793-95-4

C18H27O6PSi

Conditions
ConditionsYield
In dichloromethane at 0℃;100%
furfural
98-01-1

furfural

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one
120996-76-1

1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In ethanol for 6h; Reflux;91%
With piperidine at 140℃; for 0.05h; Microwave irradiation;87.2%
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

C25H18O4

C25H18O4

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In ethanol for 6h; Claisen-Schmidt Condensation; Reflux;
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

3-methoxy-4-(phenylmethoxy)benzaldehyde
2426-87-1

3-methoxy-4-(phenylmethoxy)benzaldehyde

C26H20O5

C26H20O5

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In ethanol for 6h; Claisen-Schmidt Condensation; Reflux;
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

salicylaldehyde
90-02-8

salicylaldehyde

1-(3'-coumarinyl)-3-(2''-hydroxyphenyl)-2-propen-1-one
193619-94-2

1-(3'-coumarinyl)-3-(2''-hydroxyphenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With ZnS/g-C3N4 nanocomposite In ethanol for 1.5h; Claisen-Schmidt Condensation; Reflux; Green chemistry;87%
With bismuth(lll) trifluoromethanesulfonate In dichloromethane at 50℃; Claisen-Schmidt Condensation;
With potassium hydroxide at 40℃; Claisen-Schmidt Condensation;
With piperidine In ethanol
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

Thiocarbohydrazide
2231-57-4

Thiocarbohydrazide

C23H18N4O4S

C23H18N4O4S

Conditions
ConditionsYield
In ethanol; water for 6h; Reflux;100%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

4-methoxy-3-nitrobenzaldehyde
31680-08-7

4-methoxy-3-nitrobenzaldehyde

C19H13NO6

C19H13NO6

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

N-ethyl-3-carbazolealdehyde
7570-45-8

N-ethyl-3-carbazolealdehyde

C26H19NO3

C26H19NO3

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
With piperidine In ethanol for 3h; Aldol Condensation; Reflux;87%
1H-indol-2-ylcarboxaldehyde
19005-93-7

1H-indol-2-ylcarboxaldehyde

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

C20H13NO3

C20H13NO3

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

5-Nitrosalicylaldehyde
97-51-8

5-Nitrosalicylaldehyde

C18H11NO6

C18H11NO6

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
isovanillin
621-59-0

isovanillin

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

C19H14O5

C19H14O5

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

2-chloro-5-nitrobenzaldehyde
6361-21-3

2-chloro-5-nitrobenzaldehyde

C18H10ClNO5

C18H10ClNO5

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

C19H14O5

C19H14O5

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

allyl iodid
556-56-9

allyl iodid

3-(1-hydroxy-1-methyl-but-3-enyl)-chromen-2-one

3-(1-hydroxy-1-methyl-but-3-enyl)-chromen-2-one

Conditions
ConditionsYield
With indium(III) chloride; indium In N,N-dimethyl-formamide at 20℃; for 0.5h;99%
7-bromoisatin
20780-74-9

7-bromoisatin

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

(R)-7-bromo-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
1610544-32-5

(R)-7-bromo-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one

Conditions
ConditionsYield
Stage #1: 3-acetylcoumarin With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)(3-vinylquinuclidin-7-yl)methyl)urea In tetrahydrofuran at 5℃; for 0.333333h; Aldol Addition;
Stage #2: 7-bromoisatin In tetrahydrofuran at 5℃; for 24h; Aldol Addition; enantioselective reaction;
99%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

5,7-Dibromoisatin
6374-91-0

5,7-Dibromoisatin

(R)-5,7-dibromo-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
1610544-34-7

(R)-5,7-dibromo-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one

Conditions
ConditionsYield
Stage #1: 3-acetylcoumarin With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)(3-vinylquinuclidin-7-yl)methyl)urea In tetrahydrofuran at 5℃; for 0.333333h; Aldol Addition;
Stage #2: 5,7-Dibromoisatin In tetrahydrofuran at 5℃; for 24h; Aldol Addition; enantioselective reaction;
99%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

indole-2,3-dione
91-56-5

indole-2,3-dione

(R)-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
1610548-53-2

(R)-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one

Conditions
ConditionsYield
Stage #1: 3-acetylcoumarin With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R)-(6-methoxyquinolin-4-yl)(3-vinylquinuclidin-7-yl)methyl)urea In tetrahydrofuran at 5℃; for 0.333333h; Aldol Addition;
Stage #2: indole-2,3-dione In tetrahydrofuran at 5℃; for 22h; Reagent/catalyst; Solvent; Aldol Addition; enantioselective reaction;
99%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

malononitrile
109-77-3

malononitrile

3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-fluorophenyl)nicotinonitrile
1421234-48-1

2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-fluorophenyl)nicotinonitrile

Conditions
ConditionsYield
With ammonium acetate In neat (no solvent) at 100℃; for 0.25h;99%
With perchloric acid adsorbed on silica gel; ammonium acetate In neat (no solvent) at 60℃; for 1.2h; Green chemistry;94%
3-acetylcoumarin
3949-36-8

3-acetylcoumarin

1-benzyl-5-chloro-1H-indole
92433-38-0

1-benzyl-5-chloro-1H-indole

3-(1,1-bis(1-benzyl-5-chloro-1H-indol-3-yl)ethyl)-2H-chromen-2-one

3-(1,1-bis(1-benzyl-5-chloro-1H-indol-3-yl)ethyl)-2H-chromen-2-one

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In acetonitrile at 35℃; for 67h; regioselective reaction;99%
1-benzyl-5-bromo-1H-indole
10075-51-1

1-benzyl-5-bromo-1H-indole

3-acetylcoumarin
3949-36-8

3-acetylcoumarin

3-(1,1-bis(1-benzyl-5-bromo-1H-indol-3-yl)ethyl)-2H-chromen-2-one

3-(1,1-bis(1-benzyl-5-bromo-1H-indol-3-yl)ethyl)-2H-chromen-2-one

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In acetonitrile at 35℃; for 72h; regioselective reaction;99%

8-Acetyl dimethoxycoumarin Specification

The 2H-1-Benzopyran-2-one,3-acetyl-, with CAS registry number 3949-36-8, belongs to the following product categories: (1)Coumarins; (2)Coumarin; (3)Building Blocks; (4)Heterocyclic Building Blocks. It has the systematic name of 3-acetyl-2H-chromen-2-one. This chemical is a kind of yellow crystalline powder. And the chemical formula of this chemical is C11H8O3. What's more, its EINECS is 223-541-6.

Physical properties of 2H-1-Benzopyran-2-one,3-acetyl-: (1)ACD/LogP: 1.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.37; (4)ACD/LogD (pH 7.4): 1.37; (5)ACD/BCF (pH 5.5): 6.53; (6)ACD/BCF (pH 7.4): 6.53; (7)ACD/KOC (pH 5.5): 133.31; (8)ACD/KOC (pH 7.4): 133.31; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 48.96 cm3; (15)Molar Volume: 146.3 cm3; (16)Polarizability: 19.41×10-24cm3; (17)Surface Tension: 49 dyne/cm; (18)Density: 1.285 g/cm3; (19)Flash Point: 179 °C; (20)Enthalpy of Vaporization: 64.13 kJ/mol; (21)Boiling Point: 391.6 °C at 760 mmHg; (22)Vapour Pressure: 2.43E-06 mmHg at 25°C.

Preparation: this chemical can be prepared by acetoacetic acid ethyl ester and 2-hydroxy-benzaldehyde. This reaction will need reagent acetic acid anhydride.

Uses of 2H-1-Benzopyran-2-one,3-acetyl-: it can be used to produce 3-acetyl-chroman-2-one. This reaction will need reagent NaBH4 and pyridine.

When you are using this chemical, please be cautious about it as the following:
The 2H-1-Benzopyran-2-one,3-acetyl- irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(C\1=C\c2c(OC/1=O)cccc2)C
(2)InChI: InChI=1/C11H8O3/c1-7(12)9-6-8-4-2-3-5-10(8)14-11(9)13/h2-6H,1H3
(3)InChIKey: CSPIFKKOBWYOEX-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C11H8O3/c1-7(12)9-6-8-4-2-3-5-10(8)14-11(9)13/h2-6H,1H3
(5)Std. InChIKey: CSPIFKKOBWYOEX-UHFFFAOYSA-N

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