5-[(2S)-1,4-dioxaspiro[4.5]decan-2-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one

• ChemBase ID: 156227
• Molecular Formular: C12H16O6
• Molecular Mass: 256.25184
• Monoisotopic Mass: 256.09468823
• SMILES: C1CCC2(CC1)OC[C@H](O2)C1C(=C(C(=O)O1)O)O
• Canonical SMILES: O=C1OC(C(=C1O)O)[C@@H]1COC2(O1)CCCCC2
• InChI: InChI=1S/C12H16O6/c13-8-9(14)11(15)17-10(8)7-6-16-12(18-7)4-2-1-3-5-12/h7,10,13-14H,1-6H2/t7-,10?/m0/s1
• InChIKey: SKQBFUVTZXIHLB-BYDSUWOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2S)-1,4-dioxaspiro[4.5]decan-2-yl]-3,4-dihydroxy-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 5-[(2S)-1,4-dioxaspiro[4.5]decan-2-yl]-3,4-dihydroxy-5H-furan-2-one
• Synonyms: (+)-5,6-O-Cyclohexylidene-L-ascorbic acid; (+)-5,6-O-环亚己基-L-抗坏血酸

Database IDs

• CAS Number: 6614-52-4
• MDL Number: MFCD00134398
• Beilstein Number: 9139605
• PubChem SID: 162250365
• PubChem CID: 71312280

CALCULATED PROPERTIES

• Acid pKa: 4.6389656
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.12731934
• LogD (pH = 7.4): -1.650022
• Log P: 1.0434548
• Molar Refractivity: 60.9755 cm^3
• Polarizability: 23.956812 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 180 °C (dec.)(lit.); 189-191 °C
• Optical Rotation: [α]20/D +3.5±1°, c = 1% in acetone

Safety Information

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

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C12H16O6

DETAILS

Sigma Aldrich - 29397

Other Notes
Chiral starting material for the synthesis of various protected (1,2-O-cyclohexylidene) C4-chiral building blocks by H2O2 oxidation1