Tetrahydro-4H-pyran-4-one
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Tetrahydro-4H-pyran-4-one
structure -
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CAS No:
29943-42-8
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Formula:
C5H8O2
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Chemical Name:
Tetrahydro-4H-pyran-4-one
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Synonyms:
4H-Pyran-4-one,tetrahydro-;Tetrahydro-4H-pyran-4-one;Tetrahydro-4-pyrone;2,3,5,6-Tetrahydro-4-pyranone;Tetrahydro-γ-pyrone;4-Oxotetrahydropyran;4-Oxacyclohexanone;4-Tetrahydropyranone;2,3,5,6-Tetrahydropyran-4-one;3,5,6-Trihydro-2H-pyran-4-one;Tetrahydro-2H-pyran-4-one;Dihydro-2H-pyran-4(3H)-one;3,4,5,6-Tetrahydro-4H-pyran-4-one;Oxan-4-one
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CAS No:
Characteristics
26.3
-0.5
Clear colorless to pale yellow Liquid
1.0980 g/cm3 @ Temp: 20 °C
166.5 °C
134 °F
n20/D 1.452(lit.)
MISCIBLE
Keep Cold
Safety Information
III
3.2
UN 1224 3/PG 3
3
10-36/37/38
24/25-36-26
Xi,F
Keep Cold/Flammable/Irritant
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
H226
|Warning|H226 (96.49%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P321, P332+P313, P362, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 58 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Tetrahydro-4H-pyran-4-one Use and Manufacturing
30 g of the intermediate 2 was added to a mixed solvent of 200 ml of toluene and 100 ml of methanol.Add 3 g of 5percent Pd/C, hydrogenate at room temperature for 5 hours, press filter, and concentrate the filtrate to dryness.Rectification gave 26 g of tetrahydropyrone in a yield of 86percent.In a flask made of glass having an inner volume of 20 ml and equipped with a stirring device, a thermometer, a reflux condenser and a balloon filled with hydrogen were charged 577 mg (6.0 mol) of pyran-4-one, 120 mg (50percent wet product; containing 0.03 mmol as a palladium atom) of 5percent by weight palladium/carbon, 5 ml of toluene and 1 ml of ethanol, and the mixture was reacted under hydrogen atmosphere at room temperature for 3 hours with stirring. In an apparatus made of glass having an inner volume of 50 ml and equipped with a stirring device, a thermometer, a reflux condenser and a Dean-Stark device were charged 0.2 g of 5percent by weight palladium/carbon (50percent hydrated product) and 30 ml of toluene, and the mixture was refluxed under normal pressure for 30 minutes with stirring (azeotropic dehydration). Comparative (Synthesis of tetrahydropyran-4-one) In a flask made of glass having an inner volume of 20 ml and equipped with a stirring device, a thermometer, a reflux condenser and a balloon filled with hydrogen were charged 500 mg (5.1 mmol) of dihydropyran-4-one synthesized in Reference example 1, 100 mg (50percent hydrated product; containing 0.02 mmol as a palladium atom) of 5percent by weight palladium/carbon, 5 ml of toluene and 0.5 ml of ethanol, the mixture was reacted under hydrogen atmosphere at room temperature for 3 hours with stirring. After completion of the reaction, when the reaction solution was analyzed by gas chromatography (Internal standard method), 361 mg (Reaction yield: 71percent) of tetrahydropyran-4-one was found to be formed.General procedure: Phosphate buffered saline (PBS, 100 mM, pH 7.4, 1 mL) wasadded to a solution of 4 and 5 (60 lmol) in MeOH (1 mL) at rt ina sealed cuvette. UV–vis measurements were taken every 15 minfor 10 h at 667 nm. In other experiments, a solution of NaOH(0.1 M, 1 mL) was used and similar measurements made. Similarmeasurements were performed with the addition of PLE (200 lL, 9 U/lmol substrate). Further experiments were performed in thepresence of thiols. A solution of GSH (70.2 lmol) in PBS(100 mM, pH = 7.4, 1 mL) was added to a solution of 4–7(35.1 lmol) in MeOH (1 mL) at rt in a sealed cuvette. UV–vis measurementswere taken every 1 min for 90 min at 665 nm. Similarexperiments were performed using another concentration of GSH(70.2 lmol) in NaOH (0.1 M, 1 mL).
Tetrahydro-4-pyrone is used in organic synthesis as building block for more complex chemical structures because it participate in a variety of cycloaddition reactions.
Computed Properties
Molecular Weight:100.12
XLogP3:-0.5
Hydrogen Bond Acceptor Count:2
Exact Mass:100.052429494
Monoisotopic Mass:100.052429494
Topological Polar Surface Area:26.3
Heavy Atom Count:7
Complexity:70.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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