4H-Pyran-4-one

Base Information

• Chemical Name: 4H-Pyran-4-one
• CAS No.: 108-97-4
• Molecular Formula: C5H4O2
• Molecular Weight: 96.0856
• Hs Code.: 2932999099
• European Community (EC) Number: 203-634-8
• UNII: UJ7X07IM7Z
• DSSTox Substance ID: DTXSID20148352
• Nikkaji Number: J1.500H
• Wikipedia: 4-Pyrone
• Wikidata: Q3411301
• Metabolomics Workbench ID: 55734
• Mol file: 108-97-4.mol

Synonyms:4H-PYRAN-4-ONE;108-97-4;Pyran-4-one;gamma-Pyrone;4-Pyrone;.gamma.-Pyrone;4-oxo-4H-pyran;UNII-UJ7X07IM7Z;UJ7X07IM7Z;EINECS 203-634-8;4-Pyranone;4-oxo-1H-pyran;4H-pyran-4-on;4H-Pyran, 4-oxo-;CHEBI:37966;4H-Pyran-4-one, >=98%;DTXSID20148352;MFCD00006576;AKOS016008736;AS-56532;CS-0108723;FT-0626622;EN300-49123;J-002217;Q3411301;Z586248016

Chemical Property of 4H-Pyran-4-one

Chemical Property:

• Vapor Pressure: 0.173mmHg at 25°C
• Melting Point: 32-34 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 212.5 °C at 760 mmHg
• Flash Point: 101.1 °C
• PSA: 30.21000
• Density: 1.192 g/cm³
• LogP: 0.63980
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 96.021129366
• Heavy Atom Count: 7
• Complexity: 119

Purity/Quality:

98% ^*data from raw suppliers

4H-Pyran-4-one ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=COC=CC1=O
• General Description: 4H-Pyran-4-one (also known as 4-pyrone, gamma-pyrone, or pyran-4-one) is a heterocyclic compound that can be synthesized via [4+2]-cycloaddition reactions of ketenes with electron-rich conjugated dienes, followed by rearrangement of the intermediate dihydropyrans. This method provides a streamlined, one-step approach to 4-pyrones, contrasting with conventional multi-step syntheses. The reaction proceeds through a dipolar intermediate stabilized by electron-donating substituents on the diene, demonstrating broad applicability for ketenes and suitably substituted dienes.

Technology Process of 4H-Pyran-4-one

There total 20 articles about 4H-Pyran-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,5-diethoxypentane-1,4-dien-3-one (135203-27-9) → 4-pyrone (108-97-4)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 24h;

DOI:10.1002/jlcr.1767

Reference yield: 97.0%

1,1,5,5-tetramethoxypentan-3-one (159015-78-8) → 4-pyrone (108-97-4)

Guidance literature:

With hydrogenchloride; In water; at 0 - 20 ℃; for 4h; Product distribution / selectivity;

Reference yield: 96.0%

2-n-butoxy-2,3-dihydro-4-pyrone (128780-12-1) → 4-pyrone (108-97-4)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; for 0.416667h; Heating;

DOI:10.1021/jo00303a048

upstream raw materials:

pyridine

3,5-dibromo-tetrahydro-pyran-4-one

comanic acid

chelidonic acid

Downstream raw materials:

1-(4-dimethylamino-phenyl)-1H-pyridin-4-one

1-p-tolyl-1H-pyridin-4-one

1,5-di-p-toluidino-penta-1,4-dien-3-one

1-(4-chloro-phenyl)-1H-pyridin-4-one

Refernces

<4+2>-Cycloaddition Reactions of Ketenes: A Novel Synthesis of 4-Pyrones

10.1055/s-1982-29856

The research investigates the [4+2]-cycloaddition reactions of ketenes with electron-rich conjugated dienes to synthesize 4-pyrones. The study explores the cycloaddition of various ketenes, including dichloro- (2a), chloro- (2b), and diphenylketenes (2c), with dienes such as 1-methoxy-3-trimethylsiloxy-1,3-butadiene (la) and 2,4-bis[trimethylsiloxy]-1,3-pentadiene (1b). The cycloaddition products initially form dihydropyrans, which then undergo a facile rearrangement to yield the desired 4-pyrones. The reaction mechanism is proposed to occur through a dipolar intermediate, with the electron-donating substituents on the conjugated diene stabilizing the positive charge in this intermediate. The resulting 4-pyrones are obtained through a relatively simple one-step preparation, offering an attractive alternative to traditional multi-step syntheses. The study highlights the general applicability of this reaction for ketenes and electron-rich conjugated dienes with specific substituents.

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