CAS 29943-42-8|CAS 143562-54-3|oxan-4-one|4H-pyran-4-one, tetrahydro-|Tetrahydro-4H-pyran-4-one|Tetrahydro-4H-pyran-4-one 97%|四氢吡喃酮|Tetrahydro-4H-pyran-4-one|4-Oxotetrahydropyran|四氢-4H-吡喃-4-...

General Information

Structure

Molecular Formula

C₅H₈O₂

Molecular Mass

100.11582

Exact Mass

100.0524295

Charge

InChI

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

InChIKey

JMJRYTGVHCAYCT-UHFFFAOYSA-N

Canonic Smiles

O=C1CCOCC1

Isomeric Smiles

C1(=O)CCOCC1

Calculated Properties

JChem

Acid pKa

18.108286

H Acceptors

H Donor

LogD (pH = 5.5)

0.107512765

LogD (pH = 7.4)

0.107512765

Log P

0.107512765

Molar Refractivity

25.4879

Polarizability

10.005251

Polar Surface Area

26.3

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

oxan-4-one

Synonyms

Tetrahydro-4H-pyran-4-oneTetrahydro-4H-pyran-4-one 97%四氢吡喃酮Tetrahydro-4H-pyran-4-one4-Oxotetrahydropyran四氢-4H-吡喃-4-酮oxan-4-one四氢-4-吡喃-4-酮

IUPAC Traditional name

4H-pyran-4-one, tetrahydro-

Names and Identifiers

Registration numbers

Beilstein Number

106463

EC Number

249-967-2

MDL Number

MFCD00006581

CAS Number

29943-42-8143562-54-3

PubChem SID

2485186916100046624888906

PubChem CID

121599

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

198242

Application
Employed in a study of the enantioselective α-aminoxylation of ketones with nitrosobenzene and L-proline in an ionic liquid.1
Undergoes condensation reactions for the preparation of dipeptides and spiroimidazolones. Employed in Wittig reactions for the synthesis of penicillins and the A ring of Vitamin D3.
Packaging
1, 5 g in glass bottle

87475

Other Notes
Synthetic intermediate; e.g. for the preparation of the 4-methoxytetrahydropyran-4-yl protecting group1; synthesis of symmetric tetrasubstituted methanes2

Molecule Details

References

PubChem Literature

From Data Sources

• The methyl enol ether is a useful protecting agent for alcohols, e.g. in nucleotide synthesis, with the advantage over 3,4-Dihydro-2H-pyran, L02731, that no new asymmetric center is introduced on reaction with a chiral alcohol: J. Am. Chem. Soc., 89, 3366 (1967); Tetrahedron, 26, 1023, 1031 (1970).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

oxan-4-one

Synonyms

Tetrahydro-4H-pyran-4-oneTetrahydro-4H-pyran-4-one 97%四氢吡喃酮Tetrahydro-4H-pyran-4-one4-Oxotetrahydropyran四氢-4H-吡喃-4-酮oxan-4-one四氢-4-吡喃-4-酮

IUPAC Traditional name

4H-pyran-4-one, tetrahydro-

Registration numbers

Beilstein Number

106463

EC Number

249-967-2

MDL Number

MFCD00006581

CAS Number

29943-42-8143562-54-3

PubChem SID

2485186916100046624888906

PubChem CID

121599

Molecule Details

Sigma Aldrich

198242

87475

Other Notes
Synthetic intermediate; e.g. for the preparation of the 4-methoxytetrahydropyran-4-yl protecting group1; synthesis of symmetric tetrasubstituted methanes2

References

PubChem Literature

From Data Sources

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:37159