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

• ChemBase ID: 148598
• 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-/m1/s1
• InChIKey: MOILFCKRQFQVFS-BDNRQGISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
• IUPAC Traditional name: (1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol
• Synonyms: (-)-2-Hydroxyisopinocampheol; [1R-(1α,2α,3α,5α)]-2,6,6-Trimethylbicyclo[3.1.1]heptane-2,3-diol; (1R,2R,3S,5R)-(-)-Pinanediol; (-)-2-羟基异松蒎醇; [1R-(1α,2α,3α,5α)]-2,6,6-三甲基双环[3.3.1]庚烷-2,3-二醇; (1R,2R,3S,5R)-(-)-蒎烷二醇

Database IDs

• CAS Number: 22422-34-0
• MDL Number: MFCD09955216
• Beilstein Number: 2039144
• PubChem SID: 24857292; 162242773
• PubChem CID: 6553875

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: 57-59 °C(lit.)
• Boiling Point: 101-102 °C/1 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Optical Rotation: [α]21/D -8.6°, 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

Product Information

• Purity: 99%
• Optical Purity: ee: 97% (GLC)
• Empirical Formula (Hill Notation): C10H18O2

DETAILS

Sigma Aldrich - 287784

Application
Used to prepare chiral double allylation reagents.1
Packaging
1, 5 g in glass bottle