143562-54-3

Basic information

• Product Name: Tetrahydro-4H-Pyran-4-one
• Synonyms: 4-oxacyclohexanone; 2,3,5,6-Tetrahydro-4-pyranone; TetrahydroHpyranone; Tetrahydro-2H-pyran-4-one; 4-Tetrahydropyranylcarboxylic acid; Pyran-4-carboxylic acid, tetrahydro-; Tetrahydro-4H-pran-4-one; dihydro-2H-pyran-4(3H)-one; 4-THP; 4-OXOCYCLOHEXANONE; 4H-Pyran-4-one, tetrahydro-; Tetrahydro-4H-pyran-4-on; Tetranydropyran-4-one; oxan-4-one
• CAS NO: 143562-54-3
• Molecular Formula: C5H8 O2
• Molecular Weight: 0100.12
• EINECS: 249-967-2
• Mol File: 143562-54-3.mol

Chemical Properties

• Boiling Point: 167.5°Cat760mmHg
• Flash Point: 63.6°C
• Appearance: colorless liquid
• Density: 1.065g/cm³
• Vapor Pressure: 1.69mmHg at 25°C
• Refractive Index: 1.451-1.453
• Water Solubility: MISCIBLE
• CAS DataBase Reference: Tetrahydro-4H-Pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrahydro-4H-Pyran-4-one(143562-54-3)
• EPA Substance Registry System: Tetrahydro-4H-Pyran-4-one(143562-54-3)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 143562-54-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
Tetrahydro-4H-Pyran-4-one is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of new drug molecules with potential therapeutic applications.
Used in Biomolecule Research:
In the field of biomolecule research, Tetrahydro-4H-Pyran-4-one serves as a valuable building block for the design and synthesis of novel biomolecules. Its presence in natural products makes it an attractive candidate for studying biological processes and interactions.
Used in Polymer Chemistry:
Tetrahydro-4H-Pyran-4-one is used as a monomer or a component in the synthesis of polymers. Its incorporation into polymer structures can lead to new materials with improved properties, such as enhanced stability or specific binding capabilities.
Used in Materials Chemistry:
In materials chemistry, Tetrahydro-4H-Pyran-4-one is employed as a component in the development of new materials with unique properties. Its presence in the molecular structure can contribute to the overall performance and characteristics of the resulting materials, such as improved mechanical strength or specific chemical reactivity.
Used in Scientific Research:
Tetrahydro-4H-Pyran-4-one is used as a research tool in various scientific studies. Its versatile structure and presence in natural products make it an interesting subject for exploring chemical reactions, synthesis pathways, and potential applications in different fields.

InChI:InChI=1/C5H8O2/c6-5-1-3-7-4-2-5/h1-4H2

Upstream product

• 2081-44-9 Tetrahydro-pyran-4-ol 
• 108-97-4 4-pyrone 
• 67728-90-9 1,5-dimethoxypent-2-yne 
• 100960-26-7 5-acetoxy-pent-1-en-3-one 
• 3592-25-4 1,5-dichloropentan-3-one 
• 57260-92-1 4-methylsulfinyl-4-methylthiotetrahydro-4-pyrane 
• 64-17-5 ethanol 
• 64769-48-8 5-ethoxy-pent-1-en-3-yne 
• 7664-93-9 sulfuric acid 
• 53005-18-8 1,5-dimethoxy-pentan-3-one 
• 84302-42-1 2,3-dihydro-4H-pyran-4-one 
• 50675-18-8 3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde 
• 124-38-9 carbon dioxide 
• 111-44-4 3-oxa-1,5-dichloropentane 

Downstream Products

• 91332-46-6 tetrahydro-pyran-4-one-(4-nitro-phenylhydrazone) 
• 24606-03-9 tetrahydro-pyran-4-one-(2,4-dinitro-phenylhydrazone) 
• 112799-20-9 4-Pyrrolidino-tetrahydro-4H-pyran-4-carbonitril 
• 84655-51-6 4-hydroxy-4-<2-(1-methoxy-1-phenylmethyl)phen-1-yl>-2,3,5,6-tetrahydropyran 
• 4233-18-5 bicyclohexylidene 
• 2888-11-1 1,1'-bicyclohexane-1,1'-diol 
• 80879-18-1 4-(tetrahydropyranyl)cyclohexane-1,1'-diol 
• 80879-19-2 4-Cyclohexylidene-tetrahydro-pyran 
• 80879-20-5 Octahydro-[4,4']bipyranylidene 
• 131067-76-0 3-methyl-tetrahydro-pyran-4-one 
• 243968-52-7 tert-butyl 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylate 
• 1201183-48-3 C₁₄H₁₄BrNO₄ 
• 1085453-57-1 4-(4-fluorotetrahydro-2H-pyran-4-yl)benzenecarbonitrile 
• 953390-79-9 tert-butyl(3,6-dihydro-2H-pyran-4-yloxy)dimethylsilane 

Relevant articles and documents

Elemental fluorine. Part 7. New oxidation methodology

Reaction of fluorine with water in the presence of acids provides new oxidants for 'in-situ' oxidation of ketones. Direct reaction of fluorine with anhydrous alcohols and 1,2-diols provides simple methodology for oxidation to corresponding secondary ketones or α-hydroxy ketones.

Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides

A widely applicable approach was developed to synthesize ketones, esters, amides via the oxidative C?C bond cleavage of readily available alkyl aldehydes. Green and abundant molecular oxygen (O2) was used as the oxidant, and base metals (cobalt and copper) were used as the catalysts. This strategy can be extended to the one-pot synthesis of ketones from primary alcohols and α-ketoamides from aldehydes.

Tetrahydro-4 H-pyran-4-one: From the Laboratory Scale to Pilot Plant Manufacture

This study describes our recent efforts to find an efficient and scalable route to tetrahydro-4H-pyran-4-one using the commercially available starting materials. The route scouting work and the full development of an efficient access to the target are described. This work culminated in the preparation of above 20 kg of the title compound in our pilot plant facility.

Tetrahydropyranone preparation method

The invention relates to a tetrahydropyranone preparation method, the method takes acetone and diethyl oxalate as raw materials, through steps of a ring closure reaction, a decarboxylation reaction, and a reduction reaction, three-step high-yield synthesis is realized to obtain tetrahydropyranone. The tetrahydropyranone preparation method has the advantages of high yield, low cost, and easy operation, and is suitable for industrial preparation method.

Synthetic method of medical intermediate tetrahydropyran-4-one

The invention discloses a synthetic method of a medical intermediate tetrahydropyran-4-one. The synthetic method of comprises the following steps: dissolving bis(2-chloroethyl)ether in ethanol, addinga Zr-Ce-Ti-Al compound oxide and ruthenium iodide, carrying out heating to 70-90 DEG C, adding H2O, introducing CO2 under a stirring condition, controlling the pressure to be 1.1-1.6 MPa, carrying out cooling to room temperature after the reaction is completed, carrying out filtering, carrying out reduced pressure distillation to remove the ethanol and the H2O, and carrying out recrystallizing toobtain the tetrahydropyran-4-one. The synthesis method provided by the invention is simple in operation, mild in conditions and few in by-products, the product purity is high, and the product yield is high.

Synthesis of azasilacyclopentenes and silanols: Via Huisgen cycloaddition-initiated C-H bond insertion cascades

An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C-H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C-H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.

New acyloxy nitroso compounds with improved water solubility and nitroxyl (HNO) release kinetics and inhibitors of platelet aggregation

New acyloxy nitroso compounds, 4-nitrosotetrahydro-2H-pyran-4-yl 2,2,2-trichloroacetate and 4-nitrosotetrahydro-2H-pyran-4-yl 2,2-dichloropropanoate were prepared. These compounds release HNO under neutral conditions with half-lives between 50 and 120 min, identifying these HNO donors as kinetically intermediate to the much slower acetate derivative and the faster trifluoroacetic acid derivative. These compounds or HNO-derived from these compounds react with thiols, including glutathione, thiol-containing enzymes and heme-containing proteins in a similar fashion to other acyloxy nitroso compounds. HNO released from these acyloxy nitroso compounds inhibits activated platelet aggregation. These acyloxy nitroso compounds augment the range of release for this group of HNO donors and should be valuable tools in the further study of HNO biology.

Rate coefficients for the gas-phase reactions of chlorine atoms with cyclic ethers at 298 K

Rate coefficients of reactions of Cl atoms with cyclic ethers, tetrahydropyran (THP), tetrahydrofuran (THF), and dihydrofurans (2,5-DHF and 2,3-DHF) have been measured at 298 K using a relative rate method. The relative rate ratios for THP and THF are 0.80 ± 0.05 and 0.80 ± 0.08, respectively, with n-hexane as the reference molecule. The relative rate ratios for THF and 2,5-DHF with n-pentane as the reference molecule are 0.95 ± 0.07 and 1.73 ± 0.06, respectively, and for 2,5-DHF with 1-butene as reference is 1.38 ± 0.05. The average values of the rate coefficients are (2.52 ± 0.36), (2.50 ± 0.39), and (4.48 ± 0.59) × 10-10 cm3 molecule-1 s-1 for THP, THF, and 2,5-DHF, respectively. The errors quoted here for relative rate ratios are 2σ of the statistical variation in different sets of experiments. These errors, combined with the reported errors of the reference rate coefficients using the statistical error propagation equation, are the quoted errors for the rate coefficients. In the case of 2,3-DHF, after correcting for the dark reaction with CH3COCl and assuming no interference from other radical reactions, a relative rate ratio of 0.85 ± 0.16 is obtained with respect to cycloheptene, corresponding to a rate coefficient of (4.52 ± 0.99) × 10-10 cm3 molecule-1 s-1. Unlike cyclic hydrocarbons, there is no increase with increasing number of CH2 groups in these cyclic ethers whereas there is an increase in the rate coefficient with unsaturation in the ring. An attempt is also made to correlate the rate coefficients of cyclic hydrocarbons and ethers with the molecular size as well as HOMO energy.

PROCESSES FOR PRODUCING TETRAHYDROPYRAN-4-ONE AND PYRAN-4-ONE

The present invention relates to a process for preparing tetrahydropyran-4-one represented by the formula (1): which comprises reacting at least one kind of dihydropyran-4-one and pyran-4-one represented by the formula (2): wherein represents a single bond or a double bond, and hydrogen (a) in the presence of a metal catalyst, in a mixed solvent of an aprotic solvent and an alcohol solvent, or (b) in the presence of an anhydrous metal catalyst in which a hydrated metal catalyst is subjected to dehydration treatment, in a hydrophobic organic solvent.

Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 15: Regioselectivity of the opening reactions with MeOH of remote O-substituted regio- and diastereoisomeric pyranosidic epoxides under condensed- and gas-phase operating conditions

The regiochemical behavior of pairs of regio- and diastereoisomeric epoxides derived from the 3,4,5,6-tetrahydro-2H-pyrane system, bearing an acetal group as the remote functionality, was determined in the acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D3+), as the promoting agent. With only one exception, the results obtained in the opening process of these epoxides indicate the incursion in the gas-phase of D+-mediated chelated bidentate species able to modify the regiochemical result found in the methanolysis in the cd-phase.