(5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-one

• ChemBase ID: 144891
• Molecular Formular: C5H6O3
• Molecular Mass: 114.09934
• Monoisotopic Mass: 114.03169405
• SMILES: C1=CC(=O)O[C@@H]1CO
• Canonical SMILES: OC[C@H]1OC(=O)C=C1
• InChI: InChI=1S/C5H6O3/c6-3-4-1-2-5(7)8-4/h1-2,4,6H,3H2/t4-/m0/s1
• InChIKey: AWNLUIGMHSSXHB-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-one
• IUPAC Traditional name: (5S)-5-(hydroxymethyl)-5H-furan-2-one
• Synonyms: (S)-(-)-5-Hydroxymethyl-2(5H)-furanone; (S)-(-)-5-羟甲基-2(5H)-呋喃酮

Database IDs

• CAS Number: 78508-96-0
• MDL Number: MFCD00075370
• Beilstein Number: 3537455
• PubChem SID: 162239103; 24861447; 24879579
• PubChem CID: 10176122

CALCULATED PROPERTIES

• Acid pKa: 5.770434
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.28013164
• LogD (pH = 7.4): -1.7240013
• Log P: -0.093719356
• Molar Refractivity: 27.2099 cm^3
• Polarizability: 10.436676 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 39-43°C; 40-44 °C; 41-43 °C(lit.)
• Flash Point: 113 °C; 235.4 °F
• Optical Rotation: [α]20/D -144°, c = 1 in H2O; [α]20/D -148±5°, c = 1.4% in H2O; -148 (c=1.4 in water)

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (sum of enantiomers, HPLC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C5H6O3

DETAILS

Sigma Aldrich - 346861

Packaging
1 g in glass bottle
Application
Used in the preparation of partially saturated heterocycles via a diastereoselective ring chain formation.1

Sigma Aldrich - 55675

Other Notes
Chiral building block; this compound and derivatives thereof have been used in many EPC syntheses, e.g. 1,4-additions occurring on the less hindered side 1; or in stereoselective cycloaddition reactions2,3,4

REFERENCES

• Versatile chiral intermediate.
• For use in the synthesis of (1R,3S)-cis-chrysanthemic acid, see: Tetrahedron Lett., 27, 3533 (1986).
• In enantioselective synthesis of AZT: Tetrahedron Lett., 29, 5349 (1988).