(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol

• ChemBase ID: 156105
• Molecular Formular: C10H18O2
• Molecular Mass: 170.24872
• Monoisotopic Mass: 170.13067982
• SMILES: C[C@]1([C@H]2C[C@H](C2(C)C)C[C@@H]1O)O
• Canonical SMILES: O[C@H]1C[C@@H]2C[C@H]([C@@]1(C)O)C2(C)C
• InChI: InChI=1S/C10H18O2/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,11-12H,4-5H2,1-3H3/t6-,7-,8-,10+/m0/s1
• InChIKey: MOILFCKRQFQVFS-AZQAYCESSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
• IUPAC Traditional name: (1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
• Synonyms: (-)-2-Hydroxyisopinocampheol; (1R,2R,3S,5R)-2,3-Pinanediol; (-)-2-羟基异松蒎醇; (1R,2R,3S,5R)-2,3-蒎烷二醇

Database IDs

• CAS Number: 22422-34-0
• MDL Number: MFCD00010365
• Beilstein Number: 2039144
• PubChem SID: 162250243
• PubChem CID: 11859632

CALCULATED PROPERTIES

• Acid pKa: 13.601064
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.8171301
• LogD (pH = 7.4): 0.81712985
• Log P: 0.8171301
• Molar Refractivity: 46.9159 cm^3
• Polarizability: 18.930742 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 54-56 °C
• Flash Point: 110 °C; 230 °F
• Optical Rotation: [α]20/D -8.7±0.5°, c = 6.5% in toluene

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: ≥98.0% (sum of enantiomers, GC)
• Grade: purum
• Empirical Formula (Hill Notation): C10H18O2

DETAILS

Sigma Aldrich - 80594

Other Notes
cis-Glycol derived from (1R)-(+)-α-pinene by anti-hydroxylation.; Preparation of boronic esters used in highly enantioselective one-carbon homologations1,2,3