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497-23-4

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497-23-4 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 497-23-4 differently. You can refer to the following data:
1. 2(5H)-Furanone is light brown liquid
2. Colorless to pale brown-yellow clear liquid

Occurrence

Reported found in coffee

Uses

Different sources of media describe the Uses of 497-23-4 differently. You can refer to the following data:
1. 2(5H)-Furanone is employed in the preparation of 5-substituted 2(5H) furanones (gamma-butenolides) catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts through direct aldol reaction with aromatic aldehydes. Further, it is used in the synthesis of lignans by Michael addition reactions. In addition to this, it is used in three-component Michael-Aldol reactions with an aldehyde and thiolate or carbanion.
2. 2(5H)-Furanone is a heterocyclic organic compound that is used widely in the synthetic preparation of pharmaceutical goods.
3. 2(5H)-Furanone is a versatile reagent used in Michael addition reactions1 for synthesis of lignans.2 Also employed in three-component Michael-Aldol reactions with an aldehyde anda thiolate3 or carbanion.4

Definition

2(5H)-Furanone is a mycotoxin that contains an α,β-unsaturated lactone moiety.

General Description

Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains.

Hazard

Extremely toxic.

Purification Methods

Fractionally distil the lactone under reduced pressure. IR: (CCl4) 1784 and 1742 cm-1, UV no max above 205nm ( 1160 cm-1 M-1) and 1HR: (CCl3) : 2.15 (pair of triplets 1H), 3.85 (pair of triplets 1H) and 5.03 (triplet 2H). [Price & Judge Org Synth Coll Vol V 255 1973, Smith & Jones Can J Chem 37 2007, 2092 1959, Beilstein 17/9 V 112.]

Check Digit Verification of cas no

The CAS Registry Mumber 497-23-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 7 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 497-23:
(5*4)+(4*9)+(3*7)+(2*2)+(1*3)=84
84 % 10 = 4
So 497-23-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2

497-23-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L13142)  2(5H)-Furanone, 98%   

  • 497-23-4

  • 1g

  • 508.0CNY

  • Detail
  • Alfa Aesar

  • (L13142)  2(5H)-Furanone, 98%   

  • 497-23-4

  • 5g

  • 1976.0CNY

  • Detail
  • Alfa Aesar

  • (L13142)  2(5H)-Furanone, 98%   

  • 497-23-4

  • 25g

  • 7746.0CNY

  • Detail
  • Aldrich

  • (283754)  2(5H)-Furanone  98%

  • 497-23-4

  • 283754-1G

  • 862.29CNY

  • Detail
  • Aldrich

  • (283754)  2(5H)-Furanone  98%

  • 497-23-4

  • 283754-5G

  • 2,968.29CNY

  • Detail

497-23-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name but-2-en-4-olide

1.2 Other means of identification

Product number -
Other names 2-Oxo-2,5-dihydrofuran

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:497-23-4 SDS

497-23-4Synthetic route

1,4-butenediol
6117-80-2

1,4-butenediol

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With 5 wt% Pd nanoparticles loaded on phosphate anion exchanged [Mg6Al2(OH)16]CO3*xH2O; air at 50℃; under 760.051 Torr; for 6h; Reagent/catalyst; Irradiation;100%
With Celite; silver carbonate In benzene for 2h; Heating;78%
With allyl methyl carbonate; dihydridotetrakis(triphenylphosphine)ruthenium In toluene for 6h; Heating;77%
at 30℃; for 24h; Nocardia corallina B-276;50%
With sodium hydrogencarbonate; sodium carbonate at 20℃; for 3h; anodic oxidation on PbO2;
(E/Z)-trimethylsilyl 4-bromo-2-butenoate

(E/Z)-trimethylsilyl 4-bromo-2-butenoate

A

trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

B

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
at 140 - 170℃; for 1h;A 98%
B 80%
η-allylcarboxylatoruthenium(II) complex RuC3H4CO2(P(C6H4-p-Cl)3)2(CO)

η-allylcarboxylatoruthenium(II) complex RuC3H4CO2(P(C6H4-p-Cl)3)2(CO)

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With bromine In dichloromethane Ambient temperature;93%
but-3-enoic acid
625-38-7

but-3-enoic acid

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
Stage #1: but-3-enoic acid With Oxalyl bromide; dimethyl sulfoxide In dichloromethane at -10 - 20℃; Inert atmosphere;
Stage #2: With potassium carbonate In dichloromethane; water for 6h;
92%
With ammonium iodide; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 24h;63%
With [bis(acetoxy)iodo]benzene; lithium bromide In methanol at 20℃; for 1h;60%
2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With oxygen In toluene at 80℃; for 2.5h;91%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 22℃; for 6h; Reagent/catalyst;80%
With [{Cu2(5-phenyl-2,8-bis(6′-bipyridinyl)-1,9,10-anthyridine)-(μ-ClO4)2}(PF6)2]; dihydrogen peroxide; sodium acetate In water at 70℃; for 12h;63%
3-hydroxyoxolan-2-one
19444-84-9

3-hydroxyoxolan-2-one

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride at 0℃; for 0.25h;90%
Stage #1: 3-hydroxyoxolan-2-one With sulfuric acid; acetic anhydride at 0℃; for 0.25h;
Stage #2: With dmap at 100℃; for 3h;
90%
η-allylcarboxylatoruthenium(II) complex RuC3H4CO2(PPh3)2(CO)

η-allylcarboxylatoruthenium(II) complex RuC3H4CO2(PPh3)2(CO)

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With bromine In dichloromethane Ambient temperature;86%
2,5-diacetoxy-2,5-dihydrofuran
7093-88-1

2,5-diacetoxy-2,5-dihydrofuran

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃; for 12h;86%
2,5-dihydro-2,5-dimethoxyfuran
332-77-4

2,5-dihydro-2,5-dimethoxyfuran

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With hydrogenchloride In water; acetone at 20℃; for 16h;84%
With trimethylsilyl bromide In dichloromethane at 20℃;
2-ethoxy-2,5-dimethyl-2,5-dihydrofuran
20295-21-0

2-ethoxy-2,5-dimethyl-2,5-dihydrofuran

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With sulfuric acid In water; acetone at 20℃; for 12h;82%
2,5-diisopropyl-2,5-dihydrofuran
20295-22-1

2,5-diisopropyl-2,5-dihydrofuran

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With nitric acid In water; acetone at 20℃; for 12h;81%
2,5-n-butoxy-2,5-dihydrofuran
20295-23-2

2,5-n-butoxy-2,5-dihydrofuran

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With phosphoric acid In water; acetone at 20℃; for 12h;79%
Acetyl-L-carnitine
3040-38-8

Acetyl-L-carnitine

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
In acetonitrile for 24h; Heating;77%
1-iodo-butane
542-69-8

1-iodo-butane

(furan-2-yloxy)-trimethylsilane
61550-02-5

(furan-2-yloxy)-trimethylsilane

silver trifluoroacetate
2966-50-9

silver trifluoroacetate

A

5-butylfuran-2(5H)-one
30336-14-2

5-butylfuran-2(5H)-one

B

n-butyl trifluoroacetate
367-64-6

n-butyl trifluoroacetate

C

4-oxo-octanoic acid butyl ester
18688-70-5

4-oxo-octanoic acid butyl ester

D

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
In dichloromethane 1.) -78 deg C, 2.) to 10 deg C, 4 h; Further byproducts given. Title compound not separated from byproducts;A 76%
B n/a
C 3%
D n/a
(furan-2-yloxy)-trimethylsilane
61550-02-5

(furan-2-yloxy)-trimethylsilane

silver trifluoroacetate
2966-50-9

silver trifluoroacetate

A

5-butylfuran-2(5H)-one
30336-14-2

5-butylfuran-2(5H)-one

B

n-butyl trifluoroacetate
367-64-6

n-butyl trifluoroacetate

C

2-buten-4-olide
497-23-4

2-buten-4-olide

D

3-butylfuran-2(3H)-one
124083-30-3

3-butylfuran-2(3H)-one

Conditions
ConditionsYield
With 1-iodo-butane In dichloromethane 1.) -78 deg C, 2.) to 10 deg C, 4 h; Further byproducts given. Title compound not separated from byproducts;A 76%
B n/a
C n/a
D n/a
carbon monoxide
201230-82-2

carbon monoxide

(Z)-3-iodoprop-2-en-1-ol
37428-57-2, 71065-45-7, 37428-50-5

(Z)-3-iodoprop-2-en-1-ol

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With potassium carbonate; hydrazine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 25℃; under 760 Torr; for 72h;76%
2,5-bis(2-hydroxyethoxy)-2,5-dihydrofuran

2,5-bis(2-hydroxyethoxy)-2,5-dihydrofuran

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With acetic acid In water; acetone at 20℃; for 12h;73%
α-phenylsulfinyl-γ-butyrolactone
54144-98-8

α-phenylsulfinyl-γ-butyrolactone

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
In neat (no solvent) at 120℃; under 0.05 - 0.1 Torr; for 2h;72%
carbon monoxide
201230-82-2

carbon monoxide

acetylene
74-86-2

acetylene

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With hexarhodium hexadecacarbonyl; water; triethylamine In 1,4-dioxane at 50℃; under 76000 Torr; for 5h;71%
furfural
98-01-1

furfural

A

2-buten-4-olide
497-23-4

2-buten-4-olide

B

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water at 60℃; for 24h; Green chemistry;A 71%
B 11%
With dihydrogen peroxide; potassium bromide; potassium hydroxide In water at 100℃; for 3h; Concentration;A 7.1%
B 51.9%
furfural
98-01-1

furfural

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With niobium(V) acetate tetrahydrate; dihydrogen peroxide In water at 60℃; for 84h;64%
With formic acid; water; dihydrogen peroxide; sodium sulfate In ethyl acetate at 260℃; under 760.051 Torr; for 2.5h; Solvent; Reagent/catalyst;62%
With 2-(N,N-dimethylamino)ethanol; formic acid; dihydrogen peroxide; sodium sulfate In dichloromethane; water at 20℃; for 15h; Inert atmosphere;58%
2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol
5244-34-8

2,2'-ethane-1,2-diylbissulfanyl-bis-ethanol

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With pyridine; toluene-4-sulfonic acid In methanol63%
furfural
98-01-1

furfural

A

succinic acid
110-15-6

succinic acid

B

2-buten-4-olide
497-23-4

2-buten-4-olide

C

maleic acid
110-16-7

maleic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide; sodium sulfate In water; ethyl acetate at 59.84℃; for 3h; Kinetics; Solvent; Reagent/catalyst; Temperature; Concentration;A 8.5%
B 61.5%
C 6.7%
With potassium chloride; dihydrogen peroxide; potassium hydroxide In water at 100℃; for 3h; Reagent/catalyst;A 24.2%
B 10.4%
C 41.2%
With formic acid; dihydrogen peroxide; sodium sulfate In water at 59.84℃; for 3h; Kinetics; Solvent; Reagent/catalyst;A 38.3%
B 12.8%
C 17.3%
2-pentanol
584-02-1

2-pentanol

D-erythronolactone
15667-21-7

D-erythronolactone

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With methyltrioxorhenium(VII) at 155℃; for 2.5h; Inert atmosphere;57%
methacryloyl anhydride
760-93-0

methacryloyl anhydride

(3S)-hydroxy-γ-butyrolactone
5469-16-9, 58081-05-3, 131432-37-6, 7331-52-4

(3S)-hydroxy-γ-butyrolactone

A

γ-butyrolactone-3-yl methacrylate

γ-butyrolactone-3-yl methacrylate

B

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In toluene at 50℃; for 4h; Reagent/catalyst;A 55%
B 21%
4-bromomethyl-β-lactone
33282-42-7

4-bromomethyl-β-lactone

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With silver nitrate In acetic acid Heating;53%
With silver nitrate In acetic acid Heating; other γ-bromo β-lactones;53%
carbon monoxide
201230-82-2

carbon monoxide

acetylene
74-86-2

acetylene

A

4-butanolide
96-48-0

4-butanolide

B

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With water; triethylamine; (acetylacetonato)dicarbonylrhodium (l) In 1,4-dioxane at 20 - 120℃; under 2700.27 - 186019 Torr; for 2h;A 22%
B 52%
With water; triethylamine; (acetylacetonato)dicarbonylrhodium (l) In 1,4-dioxane at 20 - 120℃; under 2700.27 - 186019 Torr; for 2h;
5-hydroxydihydrofuran-2(3H)-one
50768-69-9

5-hydroxydihydrofuran-2(3H)-one

A

2-buten-4-olide
497-23-4

2-buten-4-olide

B

acrolein
107-02-8

acrolein

Conditions
ConditionsYield
at 300℃; under 760.051 Torr; for 3h; Reagent/catalyst; Temperature; Inert atmosphere;A 51.4%
B n/a
3(S)-amino-γ-butyrolactone·hydrobromide
104323-16-2

3(S)-amino-γ-butyrolactone·hydrobromide

A

4-Hydroxy-dihydro-furan-2-on
5469-16-9, 7331-52-4, 58081-05-3, 131432-37-6

4-Hydroxy-dihydro-furan-2-on

B

2-buten-4-olide
497-23-4

2-buten-4-olide

Conditions
ConditionsYield
With sodium nitroprusside; potassium carbonateA 50%
B 17%
pyrrolidine
123-75-1

pyrrolidine

2-buten-4-olide
497-23-4

2-buten-4-olide

4-pyrrolidin-1-yl-dihydrofurran-2-one

4-pyrrolidin-1-yl-dihydrofurran-2-one

Conditions
ConditionsYield
In dichloromethane for 1h; Ambient temperature;100%
In chloroform-d1 at 26.9℃; addition of bicyclic chiral guanidinium salts; reaction half life; other solvent;
With complex receptor In chloroform
piperonal
120-57-0

piperonal

2-buten-4-olide
497-23-4

2-buten-4-olide

(3,4-dimethoxybenzyl)(phenyl)sulfane
83318-94-9

(3,4-dimethoxybenzyl)(phenyl)sulfane

3-(3'',4''-dimethoxy-α-phenylthiobenzyl)-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone
118535-07-2, 118626-85-0, 118711-47-0

3-(3'',4''-dimethoxy-α-phenylthiobenzyl)-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone

Conditions
ConditionsYield
100%
With n-butyllithium 1.) THF, -78 deg C, 3 h; 2.) THF, -78 deg C, 40 min; 3.) THF, -78 deg C, 90 min; Yield given. Multistep reaction;
2-buten-4-olide
497-23-4

2-buten-4-olide

benzylamine
100-46-9

benzylamine

(R,S)-4-benzylamino-4,5-dihydro-2(3H)-furanone
127560-92-3

(R,S)-4-benzylamino-4,5-dihydro-2(3H)-furanone

Conditions
ConditionsYield
In dichloromethane for 1h; Ambient temperature;100%
In methanol at 0℃; for 24h;60%
In methanol at 0℃; for 24h;50%
2-buten-4-olide
497-23-4

2-buten-4-olide

isopropyl alcohol
67-63-0

isopropyl alcohol

4-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one
42867-48-1

4-(1-hydroxy-1-methylethyl)tetrahydrofuran-2-one

Conditions
ConditionsYield
for 13h; Inert atmosphere; Irradiation;100%
With bis(p-methoxyphenyl)methanone UV-irradiation;94%
With bis(p-methoxyphenyl)methanone for 0.166667h; UV-irradiation; Continuous-flow microreactor; Inert atmosphere; diastereoselective reaction;100 %Spectr.
2-buten-4-olide
497-23-4

2-buten-4-olide

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With hydrogen In methanol under 26252.6 Torr; for 2h; Reagent/catalyst; Autoclave;99%
With 0.5% palladium on silica gel; hydrogen In methanol at 80℃; under 26252.6 Torr; Catalytic behavior; Kinetics; Reagent/catalyst; Autoclave;92.6%
With Ni#NiO; hydrogen In ethanol at 80℃; under 22502.3 Torr; for 1h; Reagent/catalyst; Autoclave;86.6%
(E)-3-(4-chlorophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

(E)-3-(4-chlorophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

2-buten-4-olide
497-23-4

2-buten-4-olide

(S)-5-((S)-1-(4-chlorophenyl)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxopropyl)furan-2(5H)-one

(S)-5-((S)-1-(4-chlorophenyl)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxopropyl)furan-2(5H)-one

Conditions
ConditionsYield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In tetrahydrofuran at -40℃; for 24h; enantioselective reaction;99%
(E)-3-(2-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

(E)-3-(2-bromophenyl)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)prop-2-en-1-one

2-buten-4-olide
497-23-4

2-buten-4-olide

(S)-5-((S)-1-(2-bromophenyl)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxopropyl)furan-2(5H)-one

(S)-5-((S)-1-(2-bromophenyl)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxopropyl)furan-2(5H)-one

Conditions
ConditionsYield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In tetrahydrofuran at -40℃; for 24h; enantioselective reaction;99%
(3-(2-methoxyethoxy)phenyl)boronic acid
227305-67-1

(3-(2-methoxyethoxy)phenyl)boronic acid

2-buten-4-olide
497-23-4

2-buten-4-olide

4-(3-(2-methoxyethoxy)phenyl)dihydrofuran-2(3H)-one

4-(3-(2-methoxyethoxy)phenyl)dihydrofuran-2(3H)-one

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 1h; Reagent/catalyst; Microwave irradiation;99%
C24H23NOS

C24H23NOS

2-buten-4-olide
497-23-4

2-buten-4-olide

(R)-N,N-dibenzyl-3-(2-methoxyphenyl)-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)propanethioamide
1638616-36-0

(R)-N,N-dibenzyl-3-(2-methoxyphenyl)-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)propanethioamide

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; N-Methyldicyclohexylamine; (R)-segphos In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; stereoselective reaction;98%
C23H20FNS

C23H20FNS

2-buten-4-olide
497-23-4

2-buten-4-olide

(R)-N,N-dibenzyl-3-(4-fluorophenyl)-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)propanethioamide
1638616-38-2

(R)-N,N-dibenzyl-3-(4-fluorophenyl)-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)propanethioamide

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; N-Methyldicyclohexylamine; (R)-segphos In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; stereoselective reaction;98%
2-buten-4-olide
497-23-4

2-buten-4-olide

N,N-dimethylthiocrotonic amide

N,N-dimethylthiocrotonic amide

(S)-N,N-dimethyl-3-((R)-5-oxo-2,5-dihydrofuran-2-yl)butanethioamide
1638616-44-0

(S)-N,N-dimethyl-3-((R)-5-oxo-2,5-dihydrofuran-2-yl)butanethioamide

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; N-Methyldicyclohexylamine; (R)-segphos In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; stereoselective reaction;98%
(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-phenylprop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-phenylprop-2-en-1-one

2-buten-4-olide
497-23-4

2-buten-4-olide

(S)-5-((S)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxo-1-phenylpropyl)furan-2(5H)-one

(S)-5-((S)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-oxo-1-phenylpropyl)furan-2(5H)-one

Conditions
ConditionsYield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In tetrahydrofuran at -40℃; for 3h; enantioselective reaction;98%
1-aminodecane
2016-57-1

1-aminodecane

2-buten-4-olide
497-23-4

2-buten-4-olide

N-Decyl-3-decylamino-4-hydroxy-butyramide
104053-25-0

N-Decyl-3-decylamino-4-hydroxy-butyramide

Conditions
ConditionsYield
97%
In acetonitrile for 24h; Reflux;68%
1-Heptylamine
111-68-2

1-Heptylamine

2-buten-4-olide
497-23-4

2-buten-4-olide

N-heptyl-3-heptylamino-4-hydroxybutanamide
182740-75-6

N-heptyl-3-heptylamino-4-hydroxybutanamide

Conditions
ConditionsYield
In chloroform for 24h;97%
triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

2-buten-4-olide
497-23-4

2-buten-4-olide

(furan-2-yloxy)triisopropylsilane
171201-21-1

(furan-2-yloxy)triisopropylsilane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;97%
With N-ethyl-N,N-diisopropylamine In dichloromethane 0 deg C to r.t.;95%
With triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;94%
2-buten-4-olide
497-23-4

2-buten-4-olide

benzylamine
100-46-9

benzylamine

3-benzylamino-4-hydroxy-N-benzylbutanamide
169677-08-1

3-benzylamino-4-hydroxy-N-benzylbutanamide

Conditions
ConditionsYield
In chloroform for 24h;97%
C9H11NS2

C9H11NS2

2-buten-4-olide
497-23-4

2-buten-4-olide

(S)-N,N-dimethyl-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)-3-(thiophen-2-yl)propanethioamide
1638616-41-7

(S)-N,N-dimethyl-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)-3-(thiophen-2-yl)propanethioamide

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; N-Methyldicyclohexylamine; (R)-segphos In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; stereoselective reaction;97%
(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(4-fluorophenyl)prop-2-en-1-one

(E)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-(4-fluorophenyl)prop-2-en-1-one

2-buten-4-olide
497-23-4

2-buten-4-olide

(S)-5-((S)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-1-(4-fluorophenyl)-3-oxopropyl)furan-2(5H)-one

(S)-5-((S)-3-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-1-(4-fluorophenyl)-3-oxopropyl)furan-2(5H)-one

Conditions
ConditionsYield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; tetrakis(actonitrile)copper(I) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In tetrahydrofuran at -40℃; for 24h; enantioselective reaction;97%
2-buten-4-olide
497-23-4

2-buten-4-olide

ethylamine
75-04-7

ethylamine

N-Ethyl-3-ethylamino-4-hydroxy-butyramide
104053-23-8

N-Ethyl-3-ethylamino-4-hydroxy-butyramide

Conditions
ConditionsYield
Heating;96%
2-buten-4-olide
497-23-4

2-buten-4-olide

N-butylamine
109-73-9

N-butylamine

N-butyl-3-butylamino-4-hydroxybutanamide
104053-24-9

N-butyl-3-butylamino-4-hydroxybutanamide

Conditions
ConditionsYield
In chloroform for 24h;96%
Heating;94%
2-buten-4-olide
497-23-4

2-buten-4-olide

N,N-dimethylthiocinnamic amide

N,N-dimethylthiocinnamic amide

(R)-N,N-dimethyl-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)-3-phenylpropanethioamide
1638616-31-5

(R)-N,N-dimethyl-3-((S)-5-oxo-2,5-dihydrofuran-2-yl)-3-phenylpropanethioamide

Conditions
ConditionsYield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; N-Methyldicyclohexylamine; (R)-segphos In tetrahydrofuran at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Time; Inert atmosphere; stereoselective reaction;96%
2-buten-4-olide
497-23-4

2-buten-4-olide

(4S,5S)-2-[N-(2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)(methyl)amino]-2-(4-methoxyphenyl)acetonitrile
204439-58-7

(4S,5S)-2-[N-(2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl)(methyl)amino]-2-(4-methoxyphenyl)acetonitrile

prenyl bromide
870-63-3

prenyl bromide

(S)-[((4S,5S)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amino]-(4-methoxy-phenyl)-[(3R,4S)-4-(3-methyl-but-2-enyl)-5-oxo-tetrahydro-furan-3-yl]-acetonitrile

(S)-[((4S,5S)-2,2-Dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amino]-(4-methoxy-phenyl)-[(3R,4S)-4-(3-methyl-but-2-enyl)-5-oxo-tetrahydro-furan-3-yl]-acetonitrile

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -30℃; for 4h;95%
2-buten-4-olide
497-23-4

2-buten-4-olide

1-amino-2-propene
107-11-9

1-amino-2-propene

N-Allyl-3-allylamino-4-hydroxy-butyramide

N-Allyl-3-allylamino-4-hydroxy-butyramide

Conditions
ConditionsYield
In chloroform for 24h;95%
2-buten-4-olide
497-23-4

2-buten-4-olide

triisopropylsilyl trifluoromethanesulfonate

triisopropylsilyl trifluoromethanesulfonate

(furan-2-yloxy)triisopropylsilane
171201-21-1

(furan-2-yloxy)triisopropylsilane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 16h; Etherification; Aromatization;95%
(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde
3243-36-5

(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde

2-buten-4-olide
497-23-4

2-buten-4-olide

C20H30O3

C20H30O3

Conditions
ConditionsYield
Stage #1: 2-buten-4-olide With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃;
Stage #2: (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde In dichloromethane at -78℃; for 2h; Further stages.;
95%
2-buten-4-olide
497-23-4

2-buten-4-olide

phenylboronic acid
98-80-6

phenylboronic acid

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one
1008-73-7, 68844-05-3, 93601-84-4, 68844-04-2

(R)-4-phenyl-4,5-dihydrofuran-2(3H)-one

Conditions
ConditionsYield
With chlorobis(ethylene)rhodium(I) dimer; (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; potassium hydroxide In methanol; dichloromethane at 20℃; for 1h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;95%
With chlorobis(ethylene)rhodium(I) dimer; (1R,4R,7R)-N-(tert-butyl)-7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxamide In water; toluene at 100℃; for 16h; Reagent/catalyst; Inert atmosphere; enantioselective reaction;85%
With chlorobis(ethylene)rhodium(I) dimer; (R)-[6,6'-bis(bis(4-(trifluoromethyl)phenyl)phosphino)-2,2',3,3'-tetrahydro-5,5'-bibenzo[b][1,4]dioxine]; potassium hydroxide In water; toluene at 20℃; for 18h; Hayashi-Miyaura reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;77%
2-buten-4-olide
497-23-4

2-buten-4-olide

1-isoquinolone
491-30-5

1-isoquinolone

(6aR,6bR,9aR,9bS)-6,6a,6b,7-tetrahydrofuro[3',4':3,4]cyclobuta[1,2-c]isoquinoline-5,9(9aH,9bH)-dione

(6aR,6bR,9aR,9bS)-6,6a,6b,7-tetrahydrofuro[3',4':3,4]cyclobuta[1,2-c]isoquinoline-5,9(9aH,9bH)-dione

Conditions
ConditionsYield
With (-)-(1S,5S,7R)-1,5,7-Trimethyl-7-(5',6',7',8'-tetrahydro-1'-oxa-3'-azacyclopenta[b]naphthalene-2'-yl)-3-azabicyclo[3.3.1]nonan-2-one In toluene at -75℃; for 2h; Inert atmosphere; Schlenk technique; Irradiation; enantioselective reaction;95%
With C22H28N2O2 In toluene at -75℃; Inert atmosphere; Irradiation; enantioselective reaction;

497-23-4Relevant articles and documents

-

Stenberg,Perkin

, p. 323 (1963)

-

Oxidation of Diols to Lactones by Nocardia corallina B-276

Luna, Hector,Prasad, Kapa,Repic, Oljan

, p. 303 - 306 (1994)

Several synthetically useful achiral and chiral lactones with high optical purity were prepared by whole-cell oxidation of diols with Nocardia corallina.The absolute stereochemistry of the newly created stereogenic centers was established by comparison with known compounds.In all cases the products were derived fron the oxidation of the pro-S hydroxymethylene group.

Reactions of complex ligands Part 91. Application of ring closing metathesis to Fischer-type carbene complexes: Synthesis and structure of medium-sized chromium oxacycloalkenylidenes

Sültemeyer, Jan,D?tz, Karl Heinz,Hupfer, Heike,Nieger, Martin

, p. 26 - 36 (2000)

Six- and seven-membered pentacarbonyl(2-oxacycloalkenylidene) chromium complexes 17 and 6 have been synthesized in moderate to good yields from alkenyloxy(methyl)carbene complex precursors applying an α-alkylation/ruthenium based ring closing metathesis sequence. The ring-closure is hampered for β-alkylated vinylcarbene complexes which may undergo competing intermolecular cross metathesis at the alkenyloxy terminus in low yield.

-

Judge,Price

, p. 435,442 (1959)

-

No-D NMR (No-Deuterium Proton NMR) spectroscopy: A simple yet powerful method for analyzing reaction and reagent solutions

Hoye, Thomas R.,Eklov, Brian M.,Ryba, Troy D.,Voloshin, Mikhail,Yao, Letitia J.

, p. 953 - 956 (2004)

(Equation presented) The title technique is a convenient and powerful method for directly monitoring or assaying any reaction mixture or reagent solution. Examples of some common processes (Fischer esterification, lithiation, butyllithium/THF compatibility, olefin metathesis, and a quantification assay), each interrogated in its native solvent, are presented. The spectral data are easy to acquire, and the information content makes a compelling case for routine use of No-D NMR spectroscopy.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang

, (2021/09/28)

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

The effect of Br- and alkali in enhancing the oxidation of furfural to maleic acid with hydrogen peroxide

Yang, Tao,Li, Wenzhi,Ogunbiyi, Ajibola T.

, (2021/03/06)

This study was focused on investigating a novel catalytic system for the selective conversion of furfural to maleic acid (MA) in an aqueous system with hydrogen peroxide as an oxidant. A series of experiments that study the impacts of catalyst species, furfural concentration, catalyst dosage, reaction temperature, residue time, hydrogen peroxide concentration, excess water content, and solvent types on the oxidation of furfural to MA was carried out. The results showed that the co-existence of Br- and alkali sites might play a vital role in furfural oxidation, which could improve the MA yield remarkably. Under 90 °C for 3 h, 72.4 % MA yield was obtained with KOH and KBr as co-catalyst in an aqueous phase. Moreover, a possible reaction pathway of furfural oxidation was proposed on the basis of our reaction system.

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Zhou, Muxing,Gridneva, Tatiana,Zhang, Zhenfeng,He, Ende,Liu, Yangang,Zhang, Wanbin

supporting information, p. 1641 - 1645 (2020/11/30)

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.

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