Conditions | Yield |
---|---|
With tetrakis(triphenylphosphineoxide)dioxouranium(VI) perchlorate In dichloromethane-d2 at 22℃; for 2.5h; | 99% |
Conditions | Yield |
---|---|
With 18-crown-6 ether In tetrahydrofuran for 2h; Heating; | 92% |
at 140 - 150℃; | |
In N,N-dimethyl-formamide at 100℃; for 21h; | |
In N,N-dimethyl-formamide at 100℃; for 21h; |
Conditions | Yield |
---|---|
In benzene for 2h; Inert atmosphere; Reflux; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrabutylammomium bromide In acetone at 120℃; under 33753.4 Torr; for 0.5h; Inert atmosphere; Microwave irradiation; | 88% |
3,3-dimethyldioxirane
pentan-3-one
A
Acetol acetate
B
1-methyl-2-oxobutyl acetate
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A n/a B 64.6% |
3,3-dimethyldioxirane
cyclohexanone
A
Acetol acetate
B
2-acetoxycyclohexanone
Conditions | Yield |
---|---|
In acetone Heating; | A n/a B 57.6% |
methanol
Acetyl(1-chlor-1-methylethyl)peroxid
A
Acetol acetate
B
Acetyl(1-methoxy-1-methylethyl)peroxid
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In chloroform-d1 at 0℃; for 20h; Yields of byproduct given; | A n/a B 57% |
3,3-dimethyldioxirane
cyclopentanone
A
Acetol acetate
B
2-acetoxycyclopentanone
Conditions | Yield |
---|---|
In acetone Heating; | A n/a B 54.3% |
3,3-dimethyldioxirane
butanone
A
3-acetoxy-2-butanone
B
Acetol acetate
C
1-acetoxybutan-3-one
D
2-oxobutyl acetate
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A 52.3% B n/a C n/a D n/a |
In acetone Heating; Yield given. Yields of byproduct given; |
ethylbenzene
3,3-dimethyldioxirane
A
Acetol acetate
B
1-Phenylethanol
C
1-phenylethyl acetate
D
acetophenone
Conditions | Yield |
---|---|
In acetone for 48h; Ambient temperature; Further byproducts given; | A n/a B 36% C 14 % Chromat. D 50% |
3-methyl-butan-2-one
3,3-dimethyldioxirane
A
Acetol acetate
B
3-Acetoxy-3-methyl-2-butanon
C
1-(acetyloxy)-3-methyl-2-butanone
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A n/a B 43.6% C n/a |
In acetone Heating; Yield given. Yields of byproduct given; |
3,3-dimethyldioxirane
A
methanol
B
acetic acid methyl ester
C
Acetol acetate
Conditions | Yield |
---|---|
With di-isopropyl ether In acetone at 22℃; for 6h; Product distribution; Mechanism; | A 12.1% B 38.4% C 11.8% |
3,3-dimethyldioxirane
2-Pentanone
A
Acetol acetate
B
4-(acetyloxy)-2-pentanone
C
1-(acetyloxy)-2-pentanone
D
(-)-1-Ethyl-2-oxopropyl acetate
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A n/a B n/a C n/a D 35.9% |
In acetone Heating; Yield given. Yields of byproduct given; |
3,3-dimethyldioxirane
2,4-dimethylpentan-3-one
A
Acetol acetate
B
2-acetoxy-2,4-dimethyl-pentan-3-one
Conditions | Yield |
---|---|
In acetone Heating; Yields of byproduct given; | A n/a B 32% |
methanol
Allyl acetate
A
1,1,3-trimethoxypropane
B
3-acetoxypropanal
C
Acetol acetate
D
3-acetoxy-1,1-dimethoxy-propane
Conditions | Yield |
---|---|
With disodium hydrogenphosphate Product distribution; hexamethylphosphoric triamide; | A 16% B 3% C 11% D 28% |
Conditions | Yield |
---|---|
Heating; | 26.1% |
Mechanism; Heating; other substrates, other ketones, or mixtures of ketones; | 26.1% |
2,5-dimethoxy-2,5-dimethyl-1,4-dioxane
acetic anhydride
A
acetic acid methyl ester
B
Acetol acetate
2,5-dimethoxy-2,5-dimethyl-1,4-dioxane
acetyl chloride
A
acetic acid methyl ester
B
Acetol acetate
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
at 140 - 150℃; |
Conditions | Yield |
---|---|
at 55 - 65℃; in Gegenwart eines durch Erhitzen von HgO mit (C2H5)2O+BF3 und wenig Trichloressigsaeure in Methanol dargestellten Katalysators; | |
at 55 - 65℃; in Gegenwart eines aus HgO, Borfluorid-aetherat, Methanol und Trichloressigsaeure hergestellten Katalysators; | |
With boron trifluoride diethyl etherate; mercury(II) oxide |
Conditions | Yield |
---|---|
at 140 - 150℃; |
Conditions | Yield |
---|---|
With lead(IV) acetate; acetic acid |
Conditions | Yield |
---|---|
In acetic acid Heating; |
Conditions | Yield |
---|---|
(i) LDA, Et2O, (ii) air, (iii) /BRN= 385737/; Multistep reaction; |
manganese triacetate
acetone
Acetol acetate
Conditions | Yield |
---|---|
In acetic anhydride; acetic acid |
3,3-dimethyl-butan-2-one
3,3-dimethyldioxirane
A
Acetol acetate
B
4-(acetyloxy)-3,3-dimethyl-2-butanone
C
acetic acid 3,3-dimethyl-2-oxobutyl ester
Conditions | Yield |
---|---|
In acetone Heating; Yield given. Yields of byproduct given; |
Acetol acetate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h; | 100% |
Acetol acetate
methyl 2,6-di-O-benzyl-3,4-di-O-trimethylsilyl-α-D-galactopyranoside
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate In diethyl ether at -20℃; for 48h; | 97% |
Acetol acetate
(2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-((R)-1,2-bis-trimethylsilanyloxy-ethyl)-5-methoxy-tetrahydro-furan
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate In diethyl ether at -20℃; for 48h; | 96% |
Conditions | Yield |
---|---|
Stage #1: Acetol acetate; C22H36O8Si2 In dichloromethane at 20℃; for 1h; Molecular sieve; Stage #2: With trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate In dichloromethane at -50℃; for 16h; | 90% |
Acetol acetate
(S,S)-2,3-bis(O-trimethylsilyl)-1,4-bisbutane-1,2,3,4-tetrol
(S,S)-2-(acetoxymethyl)-2-methyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolane
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In chloroform Ambient temperature; | 89% |
Conditions | Yield |
---|---|
Stage #1: Acetol acetate With tert-butylamine In neat (no solvent) at 20℃; for 0.25h; Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h; Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 2h; | 89% |
Acetol acetate
p-Toluic acid
N-isocyaniminotriphenylphosphorane
benzylamine
2-(benzylamino)-2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3.25h; | 88% |
Acetol acetate
N-isocyaniminotriphenylphosphorane
m-Toluic acid
2-hydroxy-2-[5-(3-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 88% |
In water at 20℃; for 1h; Green chemistry; | 85% |
3,5-dimethylbenzoic acid
Acetol acetate
N-isocyaniminotriphenylphosphorane
benzylamine
2-(benzylamino)-2-[5-(3,5-dimethylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3.25h; | 87% |
Acetol acetate
p-Toluic acid
N-isocyaniminotriphenylphosphorane
2-hydroxy-2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]propyl acetate
Conditions | Yield |
---|---|
In water at 20℃; for 1h; Green chemistry; | 86% |
In dichloromethane at 20℃; for 1h; | 83% |
Acetol acetate
Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at -78℃; for 2h; | 83% |
Acetol acetate
anthranilic acid amide
2-acetoxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 5h; Reflux; | 80% |
3-bromobenzo[b]thiophene-2-carbaldehyde
Acetol acetate
C
(R)-4-(3-bromobenzo[b]thiophen-2-yl)-4-hydroxy-2-oxobutyl acetate
Conditions | Yield |
---|---|
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction; | A n/a B n/a C 80% |
benzothiophene-2-carboxaldehyde
Acetol acetate
C
(R)-4-(1-benzothiophen-2-yl)-4-hydroxy-2-oxobutyl acetate
Conditions | Yield |
---|---|
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction; | A n/a B n/a C 78% |
3-methylbenzo[b]thiophene-2-carboxaldehyde
Acetol acetate
B
(R)-4-hydroxy-4-(3-methylbenzo[b]thiophen-2-yl)-2-oxobutyl acetate
Conditions | Yield |
---|---|
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction; | A n/a B 78% |
Conditions | Yield |
---|---|
With pyridine; titanium tetrachloride In tetrahydrofuran; dichloromethane at 0 - 20℃; for 3h; Knoevenagel Condensation; | 74% |
Conditions | Yield |
---|---|
Stage #1: Acetol acetate; 2-(3,4-dimethoxyphenyl)-ethylamine In neat (no solvent) at 20℃; for 0.25h; Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h; Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 3h; | 73% |
Acetol acetate
heptanoic acid phenyl ester
Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at -78℃; for 2h; | 72% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating; | 71% |
Acetol acetate
Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at -78℃; for 2h; | 70% |
Conditions | Yield |
---|---|
Stage #1: Acetol acetate; 1-amino-2-propene In neat (no solvent) at 20℃; for 0.25h; Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h; Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 2h; | 69% |
Acetol acetate
ethylene glycol
methyl (2-methyl-1,3-dioxolan-2-yl)acetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene | 68% |
benzothiophene-3-carboxaldehyde
Acetol acetate
A
(R)-4-(benzo[b]thiophen-3-yl)-4-hydroxy-2-oxobutyl acetate
Conditions | Yield |
---|---|
With 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole at 0℃; for 12h; Aldol reaction; optical yield given as %ee; regioselective reaction; | A 65% B n/a C n/a |
Hippuric Acid
Acetol acetate
A
E-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one
B
Z-2-phenyl-4(2-acetoxy-1-methylethylidene)-2-oxazoline-5-one
Conditions | Yield |
---|---|
With lead acetate; acetic anhydride In tetrahydrofuran for 16h; Heating; | A 63% B 1.9% |
With lead acetate; acetic anhydride In tetrahydrofuran |
Conditions | Yield |
---|---|
Stage #1: Acetol acetate; cyclohexylmethylamine In neat (no solvent) at 20℃; for 0.25h; Stage #2: With phenylphosphonate In neat (no solvent) at 20℃; for 0.25h; Stage #3: Dimethyl phosphite In neat (no solvent) at 50℃; for 1h; | 62% |
The IUPAC name of Acetoxyacetone is 2-oxopropyl acetate. With the CAS registry number 592-20-1, it is also named as 1-Hydroxy-2-propanone acetate. The product's categories are Acetyl Group; Ester Flavor. Besides, it is clear pale yellow to amber liquid, which should be stored in refrigerator. When you are using this chemical, please do not breathe vapour. And you should avoid contact with skin and eyes. In addition, its molecular formula is C5H8O3 and molecular weight is 116.11.
The other characteristics of this product can be summarized as: (1)EINECS: 209-746-3; (2)ACD/LogP: 0.33; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.33; (5)ACD/LogD (pH 7.4): 0.33; (6)ACD/BCF (pH 5.5): 1.05; (7)ACD/BCF (pH 7.4): 1.05; (8)ACD/KOC (pH 5.5): 36.15; (9)ACD/KOC (pH 7.4): 36.15; (10)#H bond acceptors: 3; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 3; (13)Polar Surface Area: 43.37 Å2; (14)Index of Refraction: 1.399; (15)Molar Refractivity: 27.01 cm3; (16)Molar Volume: 111.6 cm3; (17)Polarizability: 10.71×10-24cm3; (18)Surface Tension: 29.7 dyne/cm; (19)Density: 1.039 g/cm3; (20)Flash Point: 51.9 °C; (21)Enthalpy of Vaporization: 39.05 kJ/mol; (22)Boiling Point: 153.7 °C at 760 mmHg; (23)Vapour Pressure: 3.29 mmHg at 25 °C.
Preparation of Acetoxyacetone: this chemical can be prepared by the reaction of cyclohexanone with dimethyldioxirane.
This reaction needs acetone by heating. The yield is 57.6 %.
Uses of Acetoxyacetone: it can react with valeric acid phenyl ester to get 2-(2-acetoxy-1-hydroxy-1-methyl-ethyl)-pentanoic acid phenyl ester.
This reaction needs TiCl4, Et3N and CH2Cl2 at temperature of -78 °C. The yield is 60 %.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CC(=O)COC(=O)C
(2)InChI: InChI=1S/C5H8O3/c1-4(6)3-8-5(2)7/h3H2,1-2H3
(3)InChIKey: DBERHVIZRVGDFO-UHFFFAOYSA-N
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