Protoanemonin supplier | CasNO.108-28-1

Name
5-methylenefuran-2(5H)-one
EINECS 203-567-4
CAS No. 108-28-1
Article Data32
CAS DataBase
Density 1.14g/cm³
Solubility
Melting Point <25 °C
Formula C₅H₄O₂
Boiling Point 219 °C at 760 mmHg
Molecular Weight 96.0856
Flash Point 81.5 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,4-Pentadienoicacid, 4-hydroxy-, g-lactone (7CI);Protoanemonin (6CI);2,4-Pentadien-4-olide;4-Hydroxy-2,4-pentadienoic acid lactone;4-Hydroxy-2,4-pentadienoic acid g-lactone;5-Methylene-2(5H)-furanone;5-Methylene-2,5-dihydrofuran-2-one;5-Methylene-2-oxodihydrofuran;Isomycin;Protoanemonene;g-Methylenebutenolide;
PSA 26.30000
LogP 0.61310

Synthetic route

: 14300-71-1
5-hydroxy-5-methyl-2(5H)-furanone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With trifluoroacetic acid In chloroform at 10 - 15℃; for 2h;	82%
With trifluorormethanesulfonic acid In chloroform-d1 for 1.5h; Molecular sieve;

: 53009-05-5
3,5-di-O-p-toluoyl-2-deoxy-D-ribono-1,4-lactone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	80%

: 10374-60-4
γ-hydroxymethyl-α,β-butenolide

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With sodium acetate Heating;	60%

: 60053-24-9
penta-3,4-dienoic acid

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With iodine; sodium hydrogencarbonate; potassium iodide In water; acetonitrile 1.) 0 deg C, in the dark; 2.) 25 deg C, 3 d;	57%
With iodine; sodium hydrogencarbonate; potassium iodide In water; acetonitrile 1.) 0 deg C, in the dark; 2.) 25 deg C, 3 d; various β-allenic acid investigated;	57%
With potassium carbonate; copper dichloride; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 70℃; for 12h;	31 % Spectr.

: 534-22-5
2-methylfuran

A: 108-28-1
protoanemonin

B: 98-01-1
furfural

C: 108-31-6
maleic anhydride

Conditions

Conditions	Yield
With air; V-Mo-O catalyst on corundizium support at 350℃; for 0.000138889h; Product distribution; var. V:Mo ratios;	A 43% B 2% C 24%
With air; vanadium-molybdenum oxide (V:Mo 3:1) oncorundizium support at 350℃; for 0.000138889h;	A 43% B 2% C 24%

...Expand

: 591-12-8
5-methyl-2-furanone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
Stage #1: 5-methyl-2-furanone With bromine In tetrachloromethane at 0℃; for 1h; Stage #2: With quinoline In benzene at 0 - 20℃; for 5h;	37%

: 6214-35-3
(Z)-3-iodoprop-2-enoic acid

: 1066-54-2
trimethylsilylacetylene

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine In 1,4-dioxane at 25 - 80℃; for 3.5h; Inert atmosphere; regioselective reaction;	15%

: 74982-59-5
5-(acetyloxy)-5-methyl-2(5H)-furanone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With acetic anhydride; acetic acid
With sulfuric acid; acetic anhydride; acetic acid
With sulfuric acid In acetic anhydride; acetic acid at 80℃;

: 68267-52-7
pent-2t-en-4-ynoic acid

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid

: 4743-82-2
4-oxo-2-pentenoic acid

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With sulfuric acid; acetic anhydride; acetic acid

: 591-12-8
5-methyl-2-furanone

A: 108-28-1
protoanemonin

B: 508-44-1, 90921-11-2
anemonin

Conditions

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane for 6h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 591-12-8
5-methyl-2-furanone

A: 108-28-1
protoanemonin

B: 72137-30-5
5-bromo-5-methyloxol-3-en-2-one

C: 85846-70-4
4-bromo-5-methyloxol-4-en-2-one

: 1424-35-7, 85846-69-1, 123694-21-3, 123694-22-4
r-4,t-5-dibromo-c-5-methyloxolan-2-one

Conditions

Conditions	Yield
With N-Bromosuccinimide; sodium hydrogencarbonate; calcium oxide In tetrachloromethane for 28h; Ambient temperature; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;

...Expand

: 15146-95-9
2-Methyl-5-tert-butylfuran

A: 110-00-9
furan

B: 534-22-5
2-methylfuran

C: 108-28-1
protoanemonin

D: 98-01-1
furfural

E: 108-31-6
maleic anhydride

F: 64122-20-9
5-(tert-butyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; vanadia; molybdenum(VI) oxide; silver(l) oxide Product distribution;

...Expand

: 13271-75-5
Trimethyl(5-methyl-2-furyl)silane

A: 110-00-9
furan

B: 534-22-5
2-methylfuran

C: 108-28-1
protoanemonin

D: 98-01-1
furfural

E: 108-31-6
maleic anhydride

F: 13529-06-1
(5-trimethylsilanyl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With oxygen; vanadia; molybdenum(VI) oxide; silver(l) oxide Product distribution;

...Expand

: 37721-43-0
N-(1-deoxy-D-fructos-1-yl)-β-alanine

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
at 195℃; for 0.25h; Product distribution; pyrolysis (various times and temperatures);
Mechanism; (14)C labelled at 1,2 and 6 positions (pyrolysis);

: 4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9
3-deoxyglucosone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
at 280℃; for 0.25h; Mechanism; pyrolysis;

: 4429-05-4
N-(1-deoxy-D-fructos-1-yl)-L-glycine

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
at 195℃; for 0.25h; Product distribution; pyrolysis (various times and temperatures);

: 123-76-2
levulinic acid

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
at 280℃; for 0.25h; Mechanism; pyrolysis;
Multi-step reaction with 2 steps 1.1: 60 percent / H3PO4 / Heating 2.1: Br2 / CCl4 / 1 h / 0 °C 2.2: 37 percent / quinoline / benzene / 5 h / 0 - 20 °C View Scheme

: 116504-11-1, 116504-23-5
(3aR,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-ethoxy-dihydro-furo[3,4-d][1,3]dioxol-4-one

A: 108-28-1
protoanemonin

B: 116504-12-2
5-(tert-Butyl-dimethyl-silanyloxymethyl)-3H-furan-2-one

C: 116561-10-5
5-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5H-furan-2-one

Conditions

Conditions	Yield
With trimellitic anhydride at 300 - 320℃; under 60 - 80 Torr; for 3h; Yield given;

...Expand

: 85694-08-2
(-)-(S)-5-iodomethyloxol-3-en-2-one

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With cyanide(1-) In dichloromethane

: 103773-19-9
methyl (Z)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-propenoate

A: 108-28-1
protoanemonin

B: 508-44-1, 90921-11-2
anemonin

Conditions

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane for 6h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

: 85694-07-1
(-)-(S)-5-methanesulfonyloxymethyloxol-3-en-2-one

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With pyrrolide anion

: 85694-06-0
(S)-(5-oxo-2,5-dihydrofuran-2-yl)methyl 4-methylbenzenesulfonate

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With cyanide(1-) In dichloromethane
Multi-step reaction with 2 steps 1: 63 percent / NaI / acetone / 8 h / Heating 2: Ag2O / CH2Cl2 View Scheme

: 122-51-0
orthoformic acid triethyl ester

: 5336-08-3
D-Ribono-1,4-lactone

A: 108-28-1
protoanemonin

B: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

Conditions

Conditions	Yield
1.) THF, reflux; 2.) 220 deg C, 18 Hgmm; Multistep reaction;

...Expand

: 85694-08-2
(-)-(S)-5-iodomethyloxol-3-en-2-one

: 71-36-3
butan-1-ol

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With silver(l) oxide In dichloromethane

α-angelicalactone: α-angelicalactone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
With carbon disulfide; bromine Behandeln einer Loesung des Reaktionsprodukts in Benzol oder Aether in Chinolin;

γ-acetoxy-γ-methyl-Δα.β-crotonoactone: γ-acetoxy-γ-methyl-Δα.β-crotonoactone

: 108-28-1
protoanemonin

Conditions

Conditions	Yield
bei der trocknen Destillation;

: 74982-59-5
5-(acetyloxy)-5-methyl-2(5H)-furanone

: 7664-93-9
sulfuric acid

: 108-24-7
acetic anhydride

: 64-19-7
acetic acid

: 108-28-1
protoanemonin

...Expand

: 644-69-9
(-)-ranunculin

aqueous sodium acetate solution: aqueous sodium acetate solution

: 108-28-1
protoanemonin

: 108-28-1
protoanemonin

: potassium phenyltrifluoborate

: 126833-53-2
4-phenyl-5-methylenedihydrofuran-2-one

Conditions

Conditions	Yield
With 2-methoxy-phenol; bis(1,5-cyclooctadiene)rhodium(I) hexafluorophosphate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In toluene at 110 - 115℃; for 20h;	90%

: 108-28-1
protoanemonin

: 106-99-0
buta-1,3-diene

: 84477-25-8
1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 155℃; for 4h;	85%
at 180℃;	34%

: 108-28-1
protoanemonin

: 513-81-5
2,3-dimethyl-buta-1,3-diene

: 126109-77-1
7,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 170℃; for 4h;	81%
With hydroquinone at 162℃; for 4h;	81%

: 108-28-1
protoanemonin

: 926-54-5
trans-2-methyl-1,3-pentadiene

: 126036-63-3
6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 159℃; for 4h;	80%

: 108-28-1
protoanemonin

: 78-79-5
isoprene

: 126036-64-4
8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 154℃; for 4h; Further byproducts given;	75%

: 108-28-1
protoanemonin

: 38435-51-7
N-hydroxy-4-methoxy-benzenecarboximidoyl chloride

: 3,3'-bis(p-anisyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Conditions

Conditions	Yield
With triethylamine; hydroquinone In diethyl ether at 20℃;	74%

: 108-28-1
protoanemonin

: 2004-70-8
1-methylbuta-1,3-diene

: 126036-62-2
6-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 150℃; for 4h;	72%

: 108-28-1
protoanemonin

: 926-54-5
trans-2-methyl-1,3-pentadiene

A: 7,9-Dimethyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

B: 126036-63-3
6,8-dimethyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 150℃; for 4h;	A n/a B 70%

...Expand

: 108-28-1
protoanemonin

: 36288-37-6
N-hydroxy-4-methylbenzenecarboximidoyl chloride

: 3,3'-Di-p-tolyl-4,5-dihydro-[5,5']biisoxazolyl

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	70%

: 108-28-1
protoanemonin

: 36288-37-6
N-hydroxy-4-methylbenzenecarboximidoyl chloride

: 292605-27-7
3,3'-bis(p-tolyl)-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Conditions

Conditions	Yield
With triethylamine; hydroquinone In diethyl ether at 20℃;	69%

: 108-28-1
protoanemonin

: 78-79-5
isoprene

A: 126036-65-5
7-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

B: 126036-64-4
8-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 155℃; for 4h;	A n/a B 65%
aluminium trichloride In dichloromethane for 21h; Product distribution; Ambient temperature; also without catalyst, various dienes, other temp., time, solvent;
at 108℃; Kinetics; Thermodynamic data; energy barriers: Ep, Em; other temp.;

...Expand

: 108-28-1
protoanemonin

: 2004-70-8
1-methylbuta-1,3-diene

A: 9-Methyl-1-oxa-spiro[4.5]deca-3,7-dien-2-one

B: 126036-62-2
6-methyl-1-oxaspiro<4.5>deca-3,7-dien-2-one

Conditions

Conditions	Yield
With hydroquinone at 150℃; for 4h;	A n/a B 64%

...Expand

: 108-28-1
protoanemonin

A: 463-49-0
1,2-propanediene

B: 930-60-9
maleic anhydride

C: 74-99-7
prop-1-yne

Conditions

Conditions	Yield
at 1100℃;	A 10% B 60% C 25%

...Expand

: 108-28-1
protoanemonin

: 38435-51-7
N-hydroxy-4-methoxy-benzenecarboximidoyl chloride

: 3,3'-Bis-(4-methoxy-phenyl)-4,5-dihydro-[5,5']biisoxazolyl

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	60%

: 108-28-1
protoanemonin

: 698-16-8
benzohydroximoyl chloride

: 292605-26-6
3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

Conditions

Conditions	Yield
With triethylamine; hydroquinone In diethyl ether at 20℃;	60%

: 108-28-1
protoanemonin

: 1426817-89-1
C17H30N2O5Si

: C22H34O7Si

Conditions

Conditions	Yield
With rhodium(II) acetate dimer In toluene at 25℃;	60%

: 108-28-1
protoanemonin

: 573692-80-5
tert-butyl 2-diazo-3,6-dioxoheptanoate

: C16H20O6

Conditions

Conditions	Yield
With rhodium(II) acetate dimer In toluene at 25℃;	59%

: 108-28-1
protoanemonin

: 1165952-91-9
cyclohexa-1,3-diene

: 130619-40-8, 130696-40-1
3-((1R*,2S*,4R*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone

: 130619-40-8, 130696-40-1
3-((1R*,2R*,4R*)-2-Hydroxybicyclo<2.2.2>oct-5-en-2-yl)propanoic acid 1,4-lactone

Conditions

Conditions	Yield
In dichloromethane at 165℃; for 2h;	A 54% B 24%

...Expand

: 108-28-1
protoanemonin

: 508-44-1, 90921-11-2
anemonine

Conditions

Conditions	Yield
	53%

: 108-28-1
protoanemonin

: 542-92-7
cyclopenta-1,3-diene

: 130619-39-5, 130696-39-8
(1SR, 2RS, 4SR)-3-(2-hydroxybicyclo[2.2.1]hept-5-en-2-yl)prop-2-enoic acid lactone

: 130619-39-5, 130696-39-8
(1SR, 2SR, 4SR)-3-(2-hydroxybicyclo[2.2.1]hept-5-en-2-yl)prop-2-enoic acid lactone

Conditions

Conditions	Yield
In dichloromethane at 90℃; for 2h;	A 22% B 52%
In dichloromethane at 60℃; for 70.7h; Kinetics; Product distribution; reactions at different temperatures; reactions with cyclohexadiene at different temperatures;
In dichloromethane at 160℃; for 7.5h; Yield given. Yields of byproduct given;
In dichloromethane at 60℃; for 70.7h; Yield given. Yields of byproduct given;

...Expand

: 108-28-1
protoanemonin

: 22269-68-7
N-phenyl-C-(4-nitrobenzoyl)nitrone

: (3'RS;5,5'RS)-3'-(4-nitrobenzoyl)-2'-phenyl-2',3'-dihydrospiroisoxazolino[5':5]-(5H)-furan-2-one

Conditions

Conditions	Yield
With hydroquinone In ethyl acetate at 20℃; for 24h;	52%

: 108-28-1
protoanemonin

: 698-16-8
benzohydroximoyl chloride

: anemonin

B: 292605-26-6
3,3'-diphenyl-3a,6a-dihydro-4-oxospiro[isoxazolino-5',6-isoxazolo[3,4-c]furanone]

C: 292605-22-2
2,5-dihydro-3'-phenylspiroisoxazolino-[5',5]furan-2-one

Conditions

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 24h;	A n/a B 26% C 51%

...Expand

: 108-28-1
protoanemonin

: 28123-63-9
4-chlorobenzohydroximoyl chloride

: 3,3'-Bis-(4-chloro-phenyl)-4,5-dihydro-[5,5']biisoxazolyl

Conditions

Conditions	Yield
With triethylamine In toluene for 6h; Heating;	50%

: 108-28-1
protoanemonin

: 24423-88-9
1-pyrroline N-oxide

: (2RS,3a'SR)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

: (2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

: (3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

: 508-44-1
(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione

Conditions

Conditions	Yield
In chloroform at 70℃; for 4h; Further byproducts given;	A 2% B 50% C 16 mg D 15%

...Expand

: 108-28-1
protoanemonin

: 24423-88-9
1-pyrroline N-oxide

: (2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

: (3RS,3aRS,8aRS,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

: (3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

: 508-44-1
(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione

Conditions

Conditions	Yield
In chloroform at 70℃; for 4h; Yield given. Further byproducts given. Title compound not separated from byproducts;	A 50% B n/a C 16 mg D 15%

...Expand

: 108-28-1
protoanemonin

: (2RS,3a'SR)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

: (2RS,3a'RS)-3a',4',5',6'-tetrahydrospiro(furo-2(5H),2'(3'H)-pyrrolo[1,2-b]isoxazol)-5-one

: (3RS,3aRS,8aSR,8bSR,3a'RS)-spiro[tetrahydrofuro[3,4-d]pyrrolo[1,2-b]isoxazol-3(3aH),2'(3'H)-tetrahydropyrrolo[1,2-b]isoxazol]-1(8bH)-one

: 508-44-1
(RS,RS)-1,7-dioxa-dispiro[4.0.4.2]dodeca-3,9-diene-2,8-dione

Conditions

Conditions	Yield
With 1-pyrroline N-oxide In chloroform at 70℃; for 4h; Further byproducts given;	A 2% B 50% C 16 mg D 15%

...Expand

Protoanemonin Chemical Properties

Molecular Structure of Protoanemonin (CAS NO.108-28-1):

IUPAC Name: 5-methylidenefuran-2-one
Empirical Formula: C₅H₄O₂
Molecular Weight: 96.0841
EINECS: 203-567-4
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 26.3 Å²
Index of Refraction: 1.492
Molar Refractivity: 24.45 cm³
Molar Volume: 84.2 cm³
Surface Tension: 31.1 dyne/cm
Density: 1.14 g/cm³
Flash Point: 81.5 °C
Enthalpy of Vaporization: 45.54 kJ/mol
Boiling Point: 219 °C at 760 mmHg
Vapour Pressure: 0.122 mmHg at 25°C
InChI
InChI=1/C5H4O2/c1-4-2-3-5(6)7-4/h2-3H,1H2
Smiles
C=C1C=CC(=O)O1

Protoanemonin Specification

Protoanemonin , with CAS number is 108-28-1, can be called 2(5H)-furanone, 5-methylene- ; 4-Hydroxy-2,4-pentadienoic Acid g-Lactone ; 5-Methylene-2-oxodihydrofuran ; 5-methylidenefuran-2(5H)-one .

Product Name

5-methylenefuran-2(5H)-one

Synthetic route

Protoanemonin Chemical Properties

Protoanemonin Specification

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