ethyl acetoacetate
salicylaldehyde
A
3-acetylcoumarin
B
ethyl 2-(2-hydroxybenzylidene)-3-oxobutanoate
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With piperidine In ethanol for 2h; Knoevenagel condensation; Heating; | 99% |
Phosphoric acid dimethyl ester 1-(2-oxo-2H-chromen-3-yl)-vinyl ester
3-acetylcoumarin
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 90% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammomium bromide In N,N-dimethyl-formamide at 20℃; for 3h; | 90% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With piperidine In neat (no solvent) at 20℃; Knoevenagel Condensation; | 89% |
Conditions | Yield |
---|---|
With dipotassium peroxodisulfate; methyl tri-n-octyl ammonium hydrogen sulfate In chlorobenzene at 100℃; for 8h; Sealed tube; regioselective reaction; | 88% |
3-acetylcoumarin
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; isopropyl alcohol at 90℃; for 12h; Green chemistry; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In dichloromethane at 25℃; Knoevenagel reaction; | 76% |
Conditions | Yield |
---|---|
With piperidine; acetic acid In ethanol for 4h; Heating; | 70% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
A
3-acetylcoumarin
B
3-(3,3,3-trifluoropropanoyl)-2H-chromen-2-one
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25℃; for 0.25h; Inert atmosphere; | A 5% B 57% |
acetoacetic acid methyl ester
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
N,N-dimethyl-formamide
3-acetylcoumarin
Conditions | Yield |
---|---|
With potassium fluoride at 80℃; for 5h; Inert atmosphere; | 55% |
Conditions | Yield |
---|---|
With N,N-dimethyl-aniline for 22h; Ambient temperature; | A 53% B 27% |
3-acetyl-3,4-dihydrochromen-2-one
A
3,3'-diacetyl-3,3',4,4'-tetrahydro-4,4'-biscoumarin
B
3-acetylcoumarin
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With copper(ll) bromide In acetonitrile at 20℃; for 6h; | 50% |
(3-acetyl-2-oxo-chroman-4-yl)-phosphonic acid dimethyl ester
3-acetylcoumarin
Conditions | Yield |
---|---|
under 8 Torr; for 30h; Elimination; Thermolysis; | 48% |
ethyl aminocrotonate
salicylaldehyde
A
3-acetylcoumarin
B
7-methyl<1>benzopyrano<4,3-d><1>benzoxacino<4,3-b>pyridine-6,16-dione
Conditions | Yield |
---|---|
acetic acid In ethanol for 6h; Heating; | A 45% B 15% |
3-bromoacetylcoumarin
3-acetylcoumarin
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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 |
acetic anhydride
ethyl acetoacetate
salicylaldehyde
3-acetylcoumarin
ethyl acetoacetate
salicylaldehyde
A
3-acetylcoumarin
B
7-methyl<1>benzopyrano<4,3-d><1>benzoxacino<4,3-b>pyridine-6,16-dione
Conditions | Yield |
---|---|
With ammonia; acetic acid In ethanol for 6h; Heating; Yield given; |
hydroxy-2 methyl-2 carbomethoxy-3 2H-cromene
3-acetylcoumarin
Conditions | Yield |
---|---|
With water In pyridine Heating; |
3-acetylcoumarin
Conditions | Yield |
---|---|
With water In pyridine for 4h; Heating; Yield given; |
trisdimethylamino 2-acetyl (3H)benzo[b](1H-3-oxo-pyran-1-yl)phosphorane
3-acetylcoumarin
Conditions | Yield |
---|---|
under 5 Torr; for 0.5h; Elimination; Thermolysis; |
3-acetylcoumarin
benzaldehyde
3-cinnamoyl-2H-chromen-2-one
Conditions | Yield |
---|---|
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
4-bromo-benzaldehyde
1-(3'-coumarinyl)-3-(4''-bromophenyl)-2-propen-1-one
Conditions | Yield |
---|---|
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
4-dimethylamino-benzaldehyde
1-(3'-coumarinyl)-3-(4''-dimethylaminophenyl)-2-propen-1-one
Conditions | Yield |
---|---|
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
4-chlorobenzaldehyde
1-(3'-coumarinyl)-3-(4''-chlorophenyl)-2-propen-1-one
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
4-nitrobenzaldehdye
1-(3'-coumarinyl)-3-(4''-nitrophenyl)-2-propen-1-one
Conditions | Yield |
---|---|
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
3-acetylcoumarin
triethyl phosphite
C18H27O6PSi
Conditions | Yield |
---|---|
In dichloromethane at 0℃; | 100% |
furfural
3-acetylcoumarin
1-(3'-coumarinyl)-3-(2''-furyl)-2-propen-1-one
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
With piperidine In ethanol for 6h; Claisen-Schmidt Condensation; Reflux; |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
With piperidine In ethanol for 6h; Claisen-Schmidt Condensation; Reflux; |
3-acetylcoumarin
salicylaldehyde
1-(3'-coumarinyl)-3-(2''-hydroxyphenyl)-2-propen-1-one
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
In ethanol; water for 6h; Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
With piperidine In ethanol for 3h; Aldol Condensation; Reflux; | 87% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
With indium(III) chloride; indium In N,N-dimethyl-formamide at 20℃; for 0.5h; | 99% |
7-bromoisatin
3-acetylcoumarin
(R)-7-bromo-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
Conditions | Yield |
---|---|
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
5,7-Dibromoisatin
(R)-5,7-dibromo-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
Conditions | Yield |
---|---|
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
indole-2,3-dione
(R)-3-hydroxy-3-[2-oxo-2-(2-oxo-2H-chromen-3-yl)ethyl]indolin-2-one
Conditions | Yield |
---|---|
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
malononitrile
3-Fluorobenzaldehyde
2-amino-6-(2-oxo-2H-chromen-3-yl)-4-(3-fluorophenyl)nicotinonitrile
Conditions | Yield |
---|---|
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
1-benzyl-5-chloro-1H-indole
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate In acetonitrile at 35℃; for 67h; regioselective reaction; | 99% |
1-benzyl-5-bromo-1H-indole
3-acetylcoumarin
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate In acetonitrile at 35℃; for 72h; regioselective reaction; | 99% |
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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