(1R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione

• ChemBase ID: 146392
• Molecular Formular: C10H14O2
• Molecular Mass: 166.21696
• Monoisotopic Mass: 166.09937969
• SMILES: C[C@@]12CC[C@@H](C1(C)C)C(=O)C2=O
• Canonical SMILES: O=C1C(=O)[C@]2(C([C@@H]1CC2)(C)C)C
• InChI: InChI=1S/C10H14O2/c1-9(2)6-4-5-10(9,3)8(12)7(6)11/h6H,4-5H2,1-3H3/t6-,10+/m1/s1
• InChIKey: VNQXSTWCDUXYEZ-LDWIPMOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione
• IUPAC Traditional name: (1R)-(-)-camphorquinone
• Synonyms: (±)-Camphorquinone; Camphorquinone; (1R)-(-)-2,3-Bornanedione; 2,3-Bornanedione; (1R)-(-)-Camphorquinone; (±)-Camphorquinone; (±)-樟脑醌; 樟脑醌; (1R)-(-)-樟脑醌/茨醌; (1R)-(-)-2,3-莰烷二酮; 2,3-莰烷二酮; (1R)-(-)-樟脑醌; (±)-樟脑醌

Database IDs

• CAS Number: 10373-78-1; 10334-26-6
• EC Number: 233-814-1
• MDL Number: MFCD00064160; MFCD00082863
• Beilstein Number: 1909463; 2327696
• PubChem SID: 162240589; 24847632; 24856697
• PubChem CID: 641916

CALCULATED PROPERTIES

• Acid pKa: 17.887276
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6536038
• LogD (pH = 7.4): 2.6536038
• Log P: 2.6536038
• Molar Refractivity: 45.2629 cm^3
• Polarizability: 17.841835 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 197-202°C; 197-203 °C; 197-203 °C(lit.); 200-203 °C(lit.)
• Optical Rotation: [α]20/D -101°, c = 2 in toluene; -102 (c=2 in ethanol)

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• TSCA Listed: 否
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H319-H334
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 97%; 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C10H14O2

DETAILS

Sigma Aldrich - 124893

Packaging
5, 10, 50 g in glass bottle

Sigma Aldrich - 276286

Application
Bioreduction of quinones and other ketones by red algae.1
Chiral starting material.
Packaging
5 g in glass bottle

REFERENCES

• For use in the kinetic resolution of 1,2-diols by means of diastereomeric acetal formation, see: J. Chem. Soc., Chem. Commun., 1600 (1984).