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  • 4-Hydroxy-6-methyl-2-pyrone CAS 675-10-5 triacetate lactone CAS no 675-10-5 3,5-Dihydroxysorbic acid delta-lactone

    Cas No: 675-10-5

  • USD $ 3.5-5.0 / Kiloliter

  • 5 Kiloliter

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675-10-5 Usage

Chemical Properties

white to light yellow crystal powder

Uses

4-Hydroxy-6-methylpyran-2-one was used in the synthesis of pyrano[3,2-c]pyridones with antiproliferative and apoptosis inducing activities. It was also used in the design of benzisothiazolone human leukocyte elastase inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 675-10-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,7 and 5 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 675-10:
(5*6)+(4*7)+(3*5)+(2*1)+(1*0)=75
75 % 10 = 5
So 675-10-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,8H,1H3

675-10-5 Well-known Company Product Price

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  • Aldrich

  • (H43415)  4-Hydroxy-6-methyl-2-pyrone  98%

  • 675-10-5

  • H43415-5G

  • 390.78CNY

  • Detail
  • Aldrich

  • (H43415)  4-Hydroxy-6-methyl-2-pyrone  98%

  • 675-10-5

  • H43415-25G

  • 1,120.86CNY

  • Detail

675-10-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name triacetate lactone

1.2 Other means of identification

Product number -
Other names Triacetate lactone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:675-10-5 SDS

675-10-5Synthetic route

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
771-03-9

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
With sulfuric acid In water at 130℃; for 0.216667h; Flow reactor;96%
With sulfuric acid at 130℃; for 0.25h;90%
With sulfuric acid at 130℃; for 0.25h; Cooling with ice;89%
3,5-dioxohexanoic acid
2140-49-0

3,5-dioxohexanoic acid

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride for 0.5h; Heating;94%
With 1,1'-carbonyldiimidazole In diethyl ether at 0℃; for 2h; Yield given;
2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one
130473-38-0

2,2-dimethyl-6-(2-oxo-2-methylethyl)-4H-1,3-dioxin-4-one

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
In toluene at 100℃; for 0.5h;92%
In toluene for 0.166667h; Heating;66%
In toluene Reflux;
2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione
84257-12-5

2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Heating;89%
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
771-03-9

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

2,6-dimethyl-4-oxopyran-3-carboxylic acid
3265-58-5

2,6-dimethyl-4-oxopyran-3-carboxylic acid

Conditions
ConditionsYield
With sulfuric acid In water at 130℃; for 0.25h; Temperature; Flow reactor;A 81%
B 6 %Spectr.
4-Hydroxy-6-trimethylsilanylmethyl-pyran-2-one

4-Hydroxy-6-trimethylsilanylmethyl-pyran-2-one

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;80%
2,2-dimethyl-5-(3-oxobutanoyl)-1,3-dioxane-4,6-dione
143456-22-8

2,2-dimethyl-5-(3-oxobutanoyl)-1,3-dioxane-4,6-dione

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
In toluene Heating;76%
1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

malonoyl dichloride
1663-67-8

malonoyl dichloride

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
67%
isopropenyl isopropyl ether
4188-63-0

isopropenyl isopropyl ether

malonoyl dichloride
1663-67-8

malonoyl dichloride

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

Phloroglucinmonoisopropylether
64507-45-5

Phloroglucinmonoisopropylether

Conditions
ConditionsYield
In diethyl etherA 24%
B 65%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;
Dehydracetic acid
520-45-6

Dehydracetic acid

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
In sulfuric acid; water at 120℃; for 1.5h; Deacetylation;60%
acetic anhydride
108-24-7

acetic anhydride

2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

N-(5-methyl-[1,3,4]thiadiazol-2-yl)-N-phenyl-acetamide
7118-95-8

N-(5-methyl-[1,3,4]thiadiazol-2-yl)-N-phenyl-acetamide

Conditions
ConditionsYield
With zinc(II) chloride at 23 - 25℃; for 72h;A 30%
B 57%
acetic anhydride
108-24-7

acetic anhydride

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone
75843-20-8

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide
13053-83-3

N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide

Conditions
ConditionsYield
for 0.166667h; Heating;A 50%
B 55%
propionic acid anhydride
123-62-6

propionic acid anhydride

2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-N-phenyl-propionamide

N-(5-Methyl-[1,3,4]thiadiazol-2-yl)-N-phenyl-propionamide

Conditions
ConditionsYield
With zinc(II) chloride at 23 - 25℃; for 45h;A n/a
B 54%
propionic acid anhydride
123-62-6

propionic acid anhydride

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone
75843-20-8

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one thiosemicarbazone

A

N-(5-methyl-1,3,4-thiadiazol-2-yl)-propionamide
25958-41-2

N-(5-methyl-1,3,4-thiadiazol-2-yl)-propionamide

B

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
at 120 - 130℃; for 0.25h;A 53%
B 45%
2-Methoxypropene
116-11-0

2-Methoxypropene

malonoyl dichloride
1663-67-8

malonoyl dichloride

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

5-methoxyresorcinol
2174-64-3

5-methoxyresorcinol

Conditions
ConditionsYield
In diethyl etherA 43%
B 52%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;
2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

2-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethylidene)-N-phenylhydrazinecarbothioamide

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
771-03-9

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

C

5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine
7159-68-4

5-methyl-N-phenyl-1,3,4-thiadiazol-2-amine

Conditions
ConditionsYield
In ethanol; acetic acid for 2.41667h; Heating;A 20%
B n/a
C 44%
2-ethoxyprop-1-ene
926-66-9

2-ethoxyprop-1-ene

malonoyl dichloride
1663-67-8

malonoyl dichloride

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

Phloroglucinmonoethylether
28334-98-7

Phloroglucinmonoethylether

Conditions
ConditionsYield
In diethyl etherA 42%
B 43%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
771-03-9

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

3,5-dioxohexanoic acid methyl ester
29736-80-9

3,5-dioxohexanoic acid methyl ester

C

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

Conditions
ConditionsYield
With sodium methylate In methanol; benzene for 18h; Heating;A 7%
B 18%
C 16%
phenyldiazomethane
908094-04-2

phenyldiazomethane

4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one
93338-99-9

4-methoxy-6-(phenylthiomethyl)-2H-pyran-2-one

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

meso-5,5'-(1,2-diphenyl-1,2-ethanediyl)bis(4-methoxy-6-methyl-2H-pyran-2-one)

meso-5,5'-(1,2-diphenyl-1,2-ethanediyl)bis(4-methoxy-6-methyl-2H-pyran-2-one)

(+/-)-5,5'-(1,2-diphenyl-1,2-ethanediyl)bis(4-methoxy-6-methyl-2H-pyran-2-one)

(+/-)-5,5'-(1,2-diphenyl-1,2-ethanediyl)bis(4-methoxy-6-methyl-2H-pyran-2-one)

Conditions
ConditionsYield
Multistep reaction. Yields of byproduct given;
3,5-dioxohexanoic acid methyl ester
29736-80-9

3,5-dioxohexanoic acid methyl ester

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
With sulfuric acid at 80℃;
α-acetyl-allene-α.γ-dicarboxylic acid ester

α-acetyl-allene-α.γ-dicarboxylic acid ester

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
With hydrogenchloride
With potassium hydroxide
acetylcoenzyme A
72-89-9

acetylcoenzyme A

S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
With 6-hydroxymellein synthase from carrot root cells; sodium chloride; Coenzyme A; NADPH In water at 37℃; pH=6.0; Enzyme kinetics; Further Variations:; Reagents; pH-values;
With 2-pyrone synthase
S-acetyl coenzyme A
72-89-9

S-acetyl coenzyme A

malonyl coenzyme A

malonyl coenzyme A

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

4-hydroxy-6-(2-oxopropyl)pyran-2-one
10310-07-3

4-hydroxy-6-(2-oxopropyl)pyran-2-one

Conditions
ConditionsYield
With type III polyketide synthase RppA from S. griseus; 2-hydroxyethanethiol In various solvent(s) at 37℃; for 2h; pH=7.5;A 1 % Turnov.
B 5 % Turnov.
2,7-dimethyl-4H-pyrano<3,2-c>-2H-pyran-4,5-dione
33176-11-3

2,7-dimethyl-4H-pyrano<3,2-c>-2H-pyran-4,5-dione

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / MeONa / benzene / 18 h / Heating
2: conc. H2SO4 / 80 °C
View Scheme
acetylacetone
123-54-6

acetylacetone

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) butyl-lithium, di-isopropylamine / 1.) THF, hexane, -78 deg C, 30 min; 2.) THF, hexane, up to RT
2: 94 percent / trifluoroacetic acid, trifluoroacetic anhydride / 0.5 h / Heating
View Scheme
acetylacetone enol
26567-75-9

acetylacetone enol

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: N,N'-carbonyldiimidazole (CDI) / diethyl ether / 2 h / 0 °C
View Scheme
acetylcoenzyme A
72-89-9

acetylcoenzyme A

S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

A

6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2H-pyran-2-one

6-(2,4-dihydroxy-6-methylphenyl)-4-hydroxy-2H-pyran-2-one

B

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

C

4-hydroxy-6-(2-oxopropyl)pyran-2-one
10310-07-3

4-hydroxy-6-(2-oxopropyl)pyran-2-one

D

4-hydroxy-6-(2',4'-dioxo-pentyl)-pyrone
83095-25-4

4-hydroxy-6-(2',4'-dioxo-pentyl)-pyrone

Conditions
ConditionsYield
Stage #1: acetylcoenzyme A; S-(hydrogen malonyl)coenzyme A With recombinant N-His-tagged hexaketide synthase of Drosophyllum lusitanicum Link at 30℃; for 1h; pH=7.0; aq. buffer; Enzymatic reaction;
Stage #2: Acidic aq. solution;
S-(hydrogen malonyl)coenzyme A
524-14-1

S-(hydrogen malonyl)coenzyme A

A

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

B

(E)-4-hydroxy-6-(prop-1-en-1-yl)-2H-pyran-2-one
21534-03-2

(E)-4-hydroxy-6-(prop-1-en-1-yl)-2H-pyran-2-one

C

C10H10O3
1187429-74-8

C10H10O3

D

1,3E,5E,7E,9E,11E,13E-pentadecaheptaene
676579-01-4

1,3E,5E,7E,9E,11E,13E-pentadecaheptaene

E

C12H12O3
1187429-75-9

C12H12O3

F

(3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one
1187429-73-7

(3E,5E,7E,9E,11E,13E)-pentadeca-3,5,7,9,11,13-hexaen-2-one

G

3-oxohexadeca-4,6,8,10,12,14-hexaenoic acid
1187429-71-5

3-oxohexadeca-4,6,8,10,12,14-hexaenoic acid

Conditions
ConditionsYield
With calicheamicin polyketide synthase CalE8; calicheamicin thioesterase CalE7; NADPH In glycerol at 24℃; for 2h; pH=7; aq. phosphate buffer; Enzymatic reaction;
6-(2-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one
136801-79-1

6-(2-hydroxypropyl)-2,2-dimethyl-4H-1,3-dioxin-4-one

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Dess-Martin periodane / 20 °C
2: toluene / Reflux
View Scheme
Multi-step reaction with 2 steps
1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C
2: toluene / 0.5 h / 100 °C
View Scheme
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

acetic acid
64-19-7

acetic acid

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
771-03-9

3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In toluene Reflux;100%
With dmap; dicyclohexyl-carbodiimide In toluene at 100℃; for 2h;86.4%
With dmap; dicyclohexyl-carbodiimide In toluene at 20 - 100℃;
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

4-hydroxy-6-methyl-tetrahydro-2H-pyran-2-one
27751-97-9

4-hydroxy-6-methyl-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
palladium 10% on activated carbon In butan-1-ol at 49.84℃; under 15514.9 Torr; for 8h; Product distribution / selectivity;99.4%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

3,3’-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)
82420-03-9

3,3’-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one)

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 9h;99%
With nano Fe3O4 supported carbamoylsulfamic acid functionalized on organosilicate In neat (no solvent) at 100℃; for 1h; Reagent/catalyst; Green chemistry;96%
With piperidine; acetic acid In ethanol at 60℃; for 2.5h;95%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

acetaldehyde
75-07-0

acetaldehyde

1,1-bis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethane
92405-61-3

1,1-bis(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)ethane

Conditions
ConditionsYield
With piperidine; acetic acid In ethanol for 24h; Ambient temperature;99%
In chloroform at 40℃; for 16h;60%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

1-cyclohexene-1-carboxaldehyde
1192-88-7

1-cyclohexene-1-carboxaldehyde

3-Methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran
194796-93-5

3-Methyl-1H,7H-5a,6,8,9-tetrahydro-1-oxopyrano[4,3-b][1]benzopyran

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;99%
With L-proline In ethyl acetate at 70℃; for 24h;76%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

acetone
67-64-1

acetone

4-methoxy-6-methyl-2H-pyran-2-one
672-89-9

4-methoxy-6-methyl-2H-pyran-2-one

Conditions
ConditionsYield
With potassium carbonate In various solvent(s) for 8h; Methylation; Heating;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one
92405-72-6

2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;99%
With piperidine; acetic anhydride In ethyl acetate at -10 - 85℃;66%
Stage #1: trans-Crotonaldehyde With piperidine; acetic anhydride In ethyl acetate at -10 - 85℃;
Stage #2: 4-hydroxy-6-methyl-2-pyron In ethyl acetate at 85℃; Further stages.;
66%
With piperdinium acetate; sodium sulfate In ethyl acetate at 80 - 90℃; for 18h;
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

2,2,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one
220633-52-3

2,2,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;99%
In neat (no solvent) at 20 - 120℃; for 10h; Microwave irradiation; Green chemistry;94%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

3-methylbenzene-1,2-diol
488-17-5

3-methylbenzene-1,2-diol

7,8-dihydroxy-3,6-dimethyl-1H-pyrano[4,3-b]benzofuran-1-one

7,8-dihydroxy-3,6-dimethyl-1H-pyrano[4,3-b]benzofuran-1-one

Conditions
ConditionsYield
With Trametes versicolor laccase; oxygen In acetate buffer at 20℃; for 3.5h; pH=4.37;99%
With laccase from Trametes versicolor at 20℃; for 3h; pH=4.4; aq. acetate buffer; Enzymatic reaction; regioselective reaction;99%
With sodium acetate; potassium hexacyanoferrate(III) In water80%
With sodium acetate In water Electrochemical reaction;67%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

crotonaldehyde
123-73-9

crotonaldehyde

2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one
92405-72-6

2,7-dimethyl-2H,5H-pyrano<3,2-c>pyran-5-one

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;99%
With 4 A molecular sieve In dichloromethane53%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

benzenesulfenyl chloride
931-59-9

benzenesulfenyl chloride

4-hydroxy-6-methyl-3-(phenylsulfanyl)-2H-pyran-2-one
53603-21-7

4-hydroxy-6-methyl-3-(phenylsulfanyl)-2H-pyran-2-one

Conditions
ConditionsYield
With hydrogenchloride In benzene99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

2-methyl-2-pentenal
1115-11-3

2-methyl-2-pentenal

2,3,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one

2,3,7-trimethyl-2H-pyrano[4,3-b]pyran-5-one

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

(E/Z)-3,7-dimethyl-2,6-octadienal
5392-40-5

(E/Z)-3,7-dimethyl-2,6-octadienal

2,7-dimethyl-2-(4-methyl-pent-3-enyl)-2H-pyrano[4,3-b]pyran-5-one

2,7-dimethyl-2-(4-methyl-pent-3-enyl)-2H-pyrano[4,3-b]pyran-5-one

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere;99%
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

3,5-Dibromosalicylaldehyde
90-59-5

3,5-Dibromosalicylaldehyde

6,8-dibromo-3-acetoacetylcoumarin
98253-83-9

6,8-dibromo-3-acetoacetylcoumarin

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 90℃; for 4h;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

C14H18O3
1198426-98-0

C14H18O3

Conditions
ConditionsYield
With 2,4,8,10-Tetra-tert-butyl-6-hydroxydibenzo[d,f][1,3,2]dioxaphosphepine 6-oxide; sodium sulfate In toluene at 60℃; Inert atmosphere; regioselective reaction;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

methyl benzylidenepyruvate
107969-78-8

methyl benzylidenepyruvate

(R)-methyl 2-hydroxy-7-methyl-5-oxo-4-phenyl-2,3,4,5-tetrahydropyrano[4,3-b]pyran-2-carboxylate

(R)-methyl 2-hydroxy-7-methyl-5-oxo-4-phenyl-2,3,4,5-tetrahydropyrano[4,3-b]pyran-2-carboxylate

Conditions
ConditionsYield
With C29H29F6N3OS In diethyl ether at 20℃; for 1h; Michael addition; optical yield given as %ee; enantioselective reaction;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

methyl (E)-2-oxo-4-(4-chlorophenyl)but-3-enoate
42393-11-3

methyl (E)-2-oxo-4-(4-chlorophenyl)but-3-enoate

(R)-methyl 4-(4-chlorophenyl)-2-hydroxy-7-methyl-5-oxo-2,3,4,5-tetrahydropyrano[4,3-b]pyran-2-carboxylate

(R)-methyl 4-(4-chlorophenyl)-2-hydroxy-7-methyl-5-oxo-2,3,4,5-tetrahydropyrano[4,3-b]pyran-2-carboxylate

Conditions
ConditionsYield
With C29H29F6N3OS In diethyl ether at 20℃; for 1h; Michael addition; optical yield given as %ee; enantioselective reaction;99%
2-aminopyridine
504-29-0

2-aminopyridine

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

pyrimidine-2,4,5,6(1H,3H)-tetraone
61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

pyrimidine-2,4,5,6(1H,3H)-tetraone

2-aminopyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide
1367747-80-5

2-aminopyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions
ConditionsYield
In chloroform for 5h; Reflux;99%
2-aminopyridine
504-29-0

2-aminopyridine

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

1,3-dimethylalloxan
2757-85-9

1,3-dimethylalloxan

2-aminopyridinium 3-(5-hydroxy-1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide
1367748-29-5

2-aminopyridinium 3-(5-hydroxy-1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions
ConditionsYield
In chloroform for 18h; Reflux;99%
(5-methyl-pyridin-2-yl)amine
1603-41-4

(5-methyl-pyridin-2-yl)amine

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

pyrimidine-2,4,5,6(1H,3H)-tetraone
61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

pyrimidine-2,4,5,6(1H,3H)-tetraone

2-amino-5-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide
1367748-08-0

2-amino-5-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions
ConditionsYield
In chloroform for 5h; Reflux;99%
3-methylpyridin-2-ylamine
1603-40-3

3-methylpyridin-2-ylamine

4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

pyrimidine-2,4,5,6(1H,3H)-tetraone
61066-33-9, 61066-34-0, 61066-35-1, 61127-23-9

pyrimidine-2,4,5,6(1H,3H)-tetraone

2-amino-3-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide
1367748-01-3

2-amino-3-methylpyridinium 3-(5-hydroxy-2,4,6-trioxohexahydropyrimidin-5-yl)-6-methyl-2,4-dioxo-3,4-dihydro-2H-pyran-3-ide

Conditions
ConditionsYield
In chloroform for 3h; Reflux;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

(R/S)-1,2-Butandiol-1-<(4-methylbenzol)sulfonat>
143693-24-7

(R/S)-1,2-Butandiol-1-<(4-methylbenzol)sulfonat>

4-[1-(4-toluenesulfonyloxy)but-2-yloxy]-6-methyl-2-pyrone
1642145-05-8

4-[1-(4-toluenesulfonyloxy)but-2-yloxy]-6-methyl-2-pyrone

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 25℃; Mitsunobu Displacement; Inert atmosphere;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

tributylphosphine
998-40-3

tributylphosphine

5-bromosalicyclaldehyde
1761-61-1

5-bromosalicyclaldehyde

3-((5-bromo-2-hydroxyphenyl)(tributylphosphonio)methyl)-6-methyl-2-oxo-2H-pyran-4-olate

3-((5-bromo-2-hydroxyphenyl)(tributylphosphonio)methyl)-6-methyl-2-oxo-2H-pyran-4-olate

Conditions
ConditionsYield
With pyrrolidine; benzoic acid In tetrahydrofuran at 30℃; for 5h; Schlenk technique; Inert atmosphere;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

N-(4-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)pivalamide

N-(4-(1-hydroxy-1,3-diphenylprop-2-yn-1-yl)phenyl)pivalamide

N-(4-(7-methyl-5-oxo-2,4-diphenyl-2H,5H-pyrano[4,3-b]pyran-2-yl)phenyl)pivalamide

N-(4-(7-methyl-5-oxo-2,4-diphenyl-2H,5H-pyrano[4,3-b]pyran-2-yl)phenyl)pivalamide

Conditions
ConditionsYield
With diphenyl hydrogen phosphate In dichloromethane at 20℃; for 2h;99%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

1-tert-butyldimethylsilyloxy-2-hydroxybutane
136984-23-1

1-tert-butyldimethylsilyloxy-2-hydroxybutane

4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-methyl-2-pyrone
1259313-03-5

4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-methyl-2-pyrone

Conditions
ConditionsYield
Stage #1: 4-hydroxy-6-methyl-2-pyron; 1-tert-butyldimethylsilyloxy-2-hydroxybutane With triphenylphosphine In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;
98.4%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

1-tert-butyldimethylsilyloxy-2-hydroxybutane
136984-23-1

1-tert-butyldimethylsilyloxy-2-hydroxybutane

4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-methyl-2-pyrone
1259313-03-5

4-{1-[(tert-butyldimethylsilanyloxy)methyl]propoxy}-6-methyl-2-pyrone

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 25℃; Mitsunobu Displacement; Inert atmosphere;98.4%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

3,3'-((3-nitrophenyl)methylene)bis(4-hydroxy-6-methyl-2H-pyran-2-one)
132559-96-7

3,3'-((3-nitrophenyl)methylene)bis(4-hydroxy-6-methyl-2H-pyran-2-one)

Conditions
ConditionsYield
With nano Fe3O4 supported 2-carbamoylhydrazine-1-sulfonic acid functionalized on organosilicate In neat (no solvent) at 100℃; for 0.666667h; Reagent/catalyst; Green chemistry;98%
With sodium dodecyl-sulfate In water at 90℃; for 6h;93%
With Fe3O4(at)SiO2/(CH2)3-[imidazolium-SO3H]Cl at 90℃; for 0.416667h; Green chemistry;91%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

benzaldehyde
100-52-7

benzaldehyde

4,4'-dihydroxy-6,6'-dimethyl-3,3'-(phenylmethylene)bis(pyran)-2,2'-dione
16929-83-2

4,4'-dihydroxy-6,6'-dimethyl-3,3'-(phenylmethylene)bis(pyran)-2,2'-dione

Conditions
ConditionsYield
With piperidine; acetic acid In ethanol for 2h;98%
With nano Fe3O4 supported carbamoylsulfamic acid functionalized on organosilicate In neat (no solvent) at 100℃; for 0.266667h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Green chemistry;95%
With Fe3O4(at)SiO2/(CH2)3-[imidazolium-SO3H]Cl at 90℃; for 0.25h; Green chemistry;94%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

salicylaldehyde
90-02-8

salicylaldehyde

(1-(2-oxo-2H-chromen-3-yl)butane-1,3-dione)
13252-79-4

(1-(2-oxo-2H-chromen-3-yl)butane-1,3-dione)

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolim bromide at 90℃; for 4h;98%
With β‐cyclodextrin In water at 70℃; for 0.5h; Green chemistry;97%
molecular sieve In ethanol for 0.166667h; Heating;89%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

benzylamine
100-46-9

benzylamine

(Z)-N-benzyl-5-(benzylamino)-3-oxohex-4-enamide
84259-92-7

(Z)-N-benzyl-5-(benzylamino)-3-oxohex-4-enamide

Conditions
ConditionsYield
In ethanol for 4h; Reflux;98%
In methanol for 1h; Heating; 1/1 proportion;

675-10-5Relevant articles and documents

Screening for enhanced triacetic acid lactone production by recombinant Escherichia coli expressing a designed triacetic acid lactone reporter

Tang, Shuang-Yan,Qian, Shuai,Akinterinwa, Olubolaji,Frei, Christopher S.,Gredell, Joseph A.,Cirino, Patrick C.

, p. 10099 - 10103 (2013)

Triacetic acid lactone (TAL) is a signature byproduct of polyketide synthases (PKSs) and a valuable synthetic precursor. We have developed an endogenous TAL reporter by engineering the Escherichia coli regulatory protein AraC to activate gene expression in response to TAL. The reporter enabled in vivo directed evolution of Gerbera hybrida 2-pyrone synthase activity in E. coli. Two rounds of mutagenesis and high-throughput screening yielded a variant conferring ~20-fold increased TAL production. The catalytic efficiency (kcat/Km) of the variant toward the substrate malonyl-CoA was improved 19-fold. This study broadens the utility of engineered AraC variants as customized molecular reporters. In addition, the TAL reporter can find applications in other basic PKS activity screens.

The first example of the [4+2] cycloaddition reaction of silylketenes with 1,3-dienes: A convenient preparation of 2-pyranones and isochromenes

Ito, Tatsuya,Aoyama, Toyohiko,Shioiri, Takayuki

, p. 6583 - 6586 (1993)

Silylketenes easily undergo the [4+2] cycloaddition reaction with electron-rich 1,3-dienes and o-quinodimethanes to give the corresponding 2-pyranones and isochromenes, respectively.

Synthesis, characterization and antimicrobial activity of some new azo dyes derived from 4-hydroxy-6-methyl-2H-pyran-2-one and its dihydro derivative

Ben Mohamed-Smati, Soumaya,Faraj, Fadhil Lafta,Becheker, Imène,Berredjem, Hadjira,Le Bideau, Franck,Hamdi, Maamar,Dumas, Fran?oise,Rachedi, Yahia

, (2021)

A series of new azo disperse dyes was synthesized by coupling 4-hydroxy-6-methyl-2H-pyran-2-one (triacetic acid lactone, TAL) or its hydrogenated derivative 4-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one (dihydro triacetic acid lactone, DHTAL) with diazonium salts derived from aniline, 4-bromoaniline, 4-nitroaniline, 4-methoxyaniline, 2,4-dimethoxyaniline and 2,5-dimethoxyaniline. Spectroscopic data of these dyes dissolved in five organic solvents were measured. The effects of solvent polarity, nucleophilic component and substituent nature on the visible absorption spectra of the dyes are also reported. The structures of all compounds were confirmed by FT-IR, electronic absorption in UV and visible regions, 1H, 13C and 2D NMR and high resolution mass spectroscopy (HRMS). In addition, in vitro antibacterial activity of the synthesized derivatives against Gram positive and Gram negative bacteria, both reference and clinical strains, was evaluated qualitatively and quantitatively by agar diffusion method.

Regioselective functionalization of pyrones: Facile synthesis of 6-styrylpyrones via KHMDS-mediated aldol condensation

Basu, Manas K.,Mukkanti, K.,Samala, Ramakrishna

, (2022/01/03)

Herein, we disclose our efforts directed toward the synthesis of the kavalactone-based natural product penstyrylpyrone and other related 4-OMe-2-pyrones possessing diverse substituents at the 3-, 5-, and 7-positions. Further, a facile approach to access 6-styrylpyrones via the KHMDS-mediated regioselective aldol condensation of 2-pyrones is described with moderate substrate scope and good to high yields (58–80%). The utility of this methodology was exemplified by the stereoselective construction of desmethoxyyangonin, asnipyrone A, and asnipyrone B.

The Generation of a Library of Bromodomain-Containing Protein Modulators Expedited by Continuous Flow Synthesis

Filipponi, Paolo,Baxendale, Ian R.

, p. 2000 - 2012 (2016/04/26)

A continuous flow process delivering key building blocks for a series of BCP modulator libraries is reported. A dynamically mixed flow reactor emerged as a pivotal technology in both synthesis and isolation phases enabling the processing of slurries and suspensions while maintaining high productivity and reliability. Accordingly, the synthesis of common intermediates in flow were employed to further build a pyridazone-based library (36 compounds) aimed at improving lead compound potency and selectivity while further enabling structure-activity relationship studies of a new BCP modulator family.

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