22929-52-8

Basic information

• Product Name: Dihydrofuran-3(2H)-one
• Synonyms: 3(2H)-FURANONE, DIHYDRO-;3-OXOTETRAHYDROFURAN;DIHYDRO-3(2H)-FURANONE;DIHYDRO-FURAN-3-ONE;Dihyro-3(2H)-Furanone;Oxolan-3-one;Dihydrofuran-3(2H)-one;tetrahydrofuran-3-one
• CAS NO: 22929-52-8
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.09
• EINECS: 1308068-626-2
• Product Categories: Carbonyl Compounds;Heterocycles;Heterocycle-other series
• Mol File: 22929-52-8.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 68°C/60mmHg(lit.)
• Flash Point: 56°C
• Appearance: /Liquid
• Density: 1.128 g/cm³
• Vapor Pressure: 3.72mmHg at 25°C
• Refractive Index: 1.4360-1.4400
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: Dihydrofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrofuran-3(2H)-one(22929-52-8)
• EPA Substance Registry System: Dihydrofuran-3(2H)-one(22929-52-8)

Safety Data

• Hazard Codes: Xn
• Statements: 11-19-36/37/38-22
• Safety Statements: 16-26-36/37/39-23
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 22929-52-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless transparent liquid

InChI:InChI=1/C4H6O2/c5-4-1-2-6-3-4/h1-3H2

Synthetic route

3-Hydroxytetrahydrofuran (453-20-3) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;	95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid In dichloromethane at -5 - 20℃; for 1h; Solvent;	95%

methyl 4-oxotetrahydrofuran-3-carboxylate (57595-23-0) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With sulfuric acid at 100℃; for 3h; Reagent/catalyst; Temperature;	90.7%
In sulfuric acid	6.8 g (79%)

ethyl tetrahydrofuran-3-one 4-carboxylate (89898-51-1) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With sulfuric acid at 80℃; for 5h; Reagent/catalyst;	82.3%

2,3-dihydro-2H-furan (1191-99-7) → tetrahydrofuran-3-one (22929-52-8) + RS(SR)-2,3-dibromotetrahydrofuran (20245-14-1, 52911-58-7, 138610-15-8) + trans-3-bromo-2-hydroxytetrahydrofuran

Conditions	Yield
With water; oxygen; lithium bromide; copper(ll) bromide In tetrahydrofuran at 25℃; under 760.051 Torr;	A 15% B 75% C 10%

3-hydroxyfuran (29212-66-6) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
Stage #1: 3-hydroxyfuran With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In dichloromethane; water ice-water bath; Stage #2: With sodium hypochlorite; sodium hydrogencarbonate In dichloromethane; water at 0 - 5℃; for 2.66667h;	67%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0 - 5℃; for 2.66667h; pH=9.5;	67%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0 - 5℃; for 2.66667h; pH=9.5;	67%

(+-)-tetrahydro-furan-3-ol → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With copper oxide-chromium oxide catalyst at 200 - 250℃;
With sodium dichromate; diethyl ether; sulfuric acid

2,3-dihydro-2H-furan (1191-99-7) → tetrahydrofuran-3-one (22929-52-8) + (2S,3S)-3-chlorotetrahydrofuran-2-ol (1120-74-7, 29120-51-2, 29307-02-6) + (2R,3R)-3-chlorotetrahydrofuran-2-ol + 2-chloro-3-hydroxytetrahydrofuran

Conditions	Yield
With (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl; copper dichloride; palladium (II) ion Title compound not separated from byproducts;

2,5-dihydrofuran (1708-29-8) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With dinitrogen monoxide In benzene at 220℃; for 12h; pressure;

1-butyn-4-ol (927-74-2) → tetrahydrofuran-3-one (22929-52-8)

Conditions	Yield
With 5-bromo-2-methyl-pyridine-N-oxide; [BrettPhosAu]NTf2; trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere; Darkness;	42 %Spectr.

tetrahydrofuran-3-one (22929-52-8) + 4-methoxybenzenesulfonyl hydrazide (1950-68-1) → N'-(dihydrofuran-3(2H)-ylidene)-4-methoxybenzene-sulfonohydrazide (1510865-64-1)

Conditions	Yield
In methanol at 20℃; Schlenk technique;	100%

tetrahydrofuran-3-one (22929-52-8) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N'-(dihydrofuran-3(2H)-ylidene)-4-methylbenzene-sulfonohydrazide (1708-19-6)

Conditions	Yield
In methanol at 20℃; Schlenk technique;	100%

tetrahydrofuran-3-one (22929-52-8) + C26H37FN4O4 → C30H43FN4O5

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 0.75h;	99%
Stage #1: tetrahydrofuran-3-one; C26H37FN4O4 With acetic acid In dichloromethane at 20℃; for 0.75h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;

tetrahydrofuran-3-one (22929-52-8) + acetylenemagnesium bromide (4301-14-8) → 1-ethynyl-3-oxacyclopentanol (137344-86-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;	97%
Stage #1: tetrahydrofuran-3-one; acetylenemagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran	57%

tetrahydrofuran-3-one (22929-52-8) + nitromethane (75-52-5) → 3‑nitromethylidenetetrahydrofuran

Conditions	Yield
With sodium methylate In methanol at 20 - 30℃; for 6h; Reagent/catalyst; Temperature;	96.7%

tetrahydrofuran-3-one (22929-52-8) + sodium cyanide (773837-37-9) → 3-aminotetrahydrofuran-3-carbonitrile hydrochloride

Conditions	Yield
Stage #1: tetrahydrofuran-3-one With ammonia; acetic acid In methanol at 20℃; for 0.166667h; Cooling with ice; Stage #2: sodium cyanide In methanol at 20 - 50℃; for 2h; Stage #3: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.25h;	96%

tetrahydrofuran-3-one (22929-52-8) + tert-Butoxybis(dimethylamino)methane (5815-08-7) → (E)-4-((dimethylamino)methylene)dihydrofuran-3(2H)-one

Conditions	Yield
In toluene at 20℃; for 18h;	90%

tetrahydrofuran-3-one (22929-52-8) + trimethylsilylacetylene (1066-54-2) → 3-((trimethylsilyl)ethynyl)tetrahydrofuran-3-ol

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran at -78 - 20℃; for 1.33333h;	89%
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran at -78 - 20℃; for 1.33333h; Inert atmosphere;	89%

tetrahydrofuran-3-one (22929-52-8) + phenylacetylene (536-74-3) → 3-(phenylethynyl)tetrahydrofuran-3-ol

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	89%

tetrahydrofuran-3-one (22929-52-8) + N,N-dimethylammonium chloride (506-59-2) + potassium cyanide (151-50-8) → 3-cyano-3-dimethylamino-tetrahydrofurane (176445-75-3)

Conditions	Yield
In water Ambient temperature;	88%

tetrahydrofuran-3-one (22929-52-8) + ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate → ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate

Conditions	Yield
Stage #1: tetrahydrofuran-3-one; ethyl 1-(6-(3,5-difluoro-2-((2-methyl-4-(piperidin-4-yl)benzyl)oxy)phenyl)pyridin-2-yl)piperidine-4-carboxylate In methanol at 25℃; for 3h; Molecular sieve; Stage #2: With sodium cyanoborohydride In methanol at 50℃; for 12h;	88%

tetrahydrofuran-3-one (22929-52-8) + 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate → 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(7-(tetrahydrofuran-3-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate

Conditions	Yield
Stage #1: tetrahydrofuran-3-one; 1,1,1,3,3,3-hexafluoropropan-2-yl 1-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carbonyl)-1,8-diazaspiro[4.5]decane-8-carboxylate With triethylamine In 1,2-dichloro-ethane at 20℃; for 1.5h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 4h;	86%

tetrahydrofuran-3-one (22929-52-8) + nitromethane (75-52-5) → C5H9NO4

Conditions	Yield
With triethylamine In ethanol at 20℃; for 18h;	85.9%

tetrahydrofuran-3-one (22929-52-8) + methanesulfonic acid (75-75-2) + homoalylic alcohol (627-27-0) → methanesulfonic acid 2,6-dioxaspiro[4.5]dec-9-yl ester (503551-88-0)

Conditions	Yield
In dichloromethane at 23℃; Prins cyclization;	85%
In dichloromethane at 25℃; for 16h;

tetrahydrofuran-3-one (22929-52-8) + trans-3-((2-methyl-6-(5-methyl-6-(piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol → trans-3-((2-methyl-6-(5-methyl-6-(1-(tetrahydrofuran-3-yl)piperidin-4-yl)-1H-indazol-1-yl)pyrimidin-4-yl)amino)cyclobutanol

Conditions	Yield
With sodium cyanoborohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 6h;	85%

tetrahydrofuran-3-one (22929-52-8) + isoquinoline (119-65-3) → 1-(4-oxotetrahydrofuran-2-yl)isoquinoline

Conditions	Yield
With sodium persulfate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; trifluoroacetic acid In water at 23℃; for 24h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; regioselective reaction;	83%

tetrahydrofuran-3-one (22929-52-8) + ethylamine (75-04-7) → N-ethyltetrahydrofuran-3-amine

Conditions	Yield
Stage #1: tetrahydrofuran-3-one; ethylamine With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 16h; Molecular sieve; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 2h;	83%

tetrahydrofuran-3-one (22929-52-8) + 1-bromo-4-methoxy-benzene (104-92-7) → 3-(4-methoxyphenyl)tetrahydrofuran-3-ol

Conditions	Yield
Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.416667h; Inert atmosphere; Stage #2: tetrahydrofuran-3-one In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere;	82%

Upstream product

• 57595-23-0 methyl 4-oxotetrahydrofuran-3-carboxylate 
• 89898-51-1 ethyl tetrahydrofuran-3-one 4-carboxylate 
• 927-74-2 3-Butyn-1-ol 
• 29212-66-6 3-hydroxyfuran 
• 1191-99-7 2,3-dihydro-2H-furan 
• 1708-29-8 2,5-dihydrofuran 
• 453-20-3 3-Hydroxytetrahydrofuran 

Downstream Products

• 106183-61-3 3-morpholino-4,5-dihydrofuran 
• 106183-62-4 4-(2,5-Dihydro-furan-3-yl)-morpholine 
• 81866-98-0 7-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 503551-88-0 methanesulfonic acid 2,6-dioxaspiro[4.5]dec-9-yl ester 
• 17517-50-9 9-phenyl-2,3-dihydro-furo[3,2-b]quinoline 
• 75394-90-0 3-methylene tetrahydrofuran 

Relevant articles and documents

Synthesis method of tetrahydrofuran-3-ketone

The invention discloses a synthesis method of tetrahydrofuran-3-ketone. The method comprises the following steps of: under an alkaline condition, mixing glycolate (I) and acrylate (II) in a solvent, and carrying out condensation cyclization reaction to obtain 4-formic ester-tetrahydrofuran-3-ketone (III); then, under an acidic condition, performing reflux decarboxylation reaction on the 4-formic ester-tetrahydrofuran-3-ketone (III) so as to obtain thetetrahydrofuran-3-ketone (IV) . According to the synthesis method of the tetrahydrofuran-3-ketone, the yield is greater than 82%; and the method has the advantages of mild and easily-controlled conditions, mild reaction, simple and safe operation and environmental friendliness.

COMPOUNDS FOR TREATMENT OF GLIOBLASTOMA

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NOVEL PROCESS FOR THE MANUFACTURE OF 3-OXO-TETRAHYDROFURAN

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