(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid

• ChemBase ID: 148896
• Molecular Formular: C10H14O4
• Molecular Mass: 198.21576
• Monoisotopic Mass: 198.08920893
• SMILES: C[C@@]12CC[C@@](C1(C)C)(OC2=O)C(=O)O
• Canonical SMILES: OC(=O)[C@@]12CC[C@](C2(C)C)(C(=O)O1)C
• InChI: InChI=1S/C10H14O4/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3,(H,11,12)/t9-,10+/m0/s1
• InChIKey: KPWKPGFLZGMMFX-VHSXEESVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
• IUPAC Traditional name: (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid
• Synonyms: (-)-Camphanic acid; (1S)-3-Oxo-4,7,7-trimethyl-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid; (1S)-(-)-Camphanic acid; (1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid; (-)-Camphanic acid; (-)-莰烷酸; (1S)-3-氧-4,7,7-三甲基-2-氧杂双环[2.2.1]庚烷-1-甲酸; (1S)-(-)-莰烷酸; (1S)-4,7,7-三甲基-3-氧-2-氧杂双环[2.2.1]庚烷-1-甲酸; (-)-莰烷酸

Database IDs

• CAS Number: 13429-83-9
• EC Number: 236-552-6
• MDL Number: MFCD00044948
• Beilstein Number: 84570
• PubChem SID: 24859723; 162243068
• PubChem CID: 719817

CALCULATED PROPERTIES

• Acid pKa: 3.7547987
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.017402854
• LogD (pH = 7.4): -1.5541
• Log P: 1.7284589
• Molar Refractivity: 46.9173 cm^3
• Polarizability: 19.06304 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 201-204 °C(lit.); 201-205 °C
• Optical Rotation: [α]20/D -18°, c = 1 in dioxane; [α]20/D -20.0±1°, c = 1% in dioxane

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); 99%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C10H14O4

DETAILS

Sigma Aldrich - 328227

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 21284

Other Notes
Reagent for the resolution of racemic alcohols1; Amide formation with a carbodiimide2; Reduction-oxidation to a hydroxymethyl-cyclopentanone building block3