(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid

• ChemBase ID: 145405
• Molecular Formular: C10H14O3
• Molecular Mass: 182.21636
• Monoisotopic Mass: 182.09429431
• SMILES: CC1([C@@H]2CC[C@]1(C(=O)C2)C(=O)O)C
• Canonical SMILES: OC(=O)[C@]12CC[C@@H](C2(C)C)CC1=O
• InChI: InChI=1S/C10H14O3/c1-9(2)6-3-4-10(9,8(12)13)7(11)5-6/h6H,3-5H2,1-2H3,(H,12,13)/t6-,10+/m1/s1
• InChIKey: WDODWBQJVMBHCO-LDWIPMOCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid
• IUPAC Traditional name: (1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid
• Synonyms: (1S)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid; (1S)-(+)-Ketopinic acid; (1S)-7,7-二甲基-2-氧代二环[2.2.1]庚烷-1-甲酸; (1S)-(+)-酮基蒎酸

Database IDs

• CAS Number: 40724-67-2
• MDL Number: MFCD00168053
• Beilstein Number: 4180005
• PubChem SID: 162239611; 24866367
• PubChem CID: 739183

CALCULATED PROPERTIES

• Acid pKa: 4.2443085
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.46783376
• LogD (pH = 7.4): -1.2581463
• Log P: 1.7446781
• Molar Refractivity: 46.2092 cm^3
• Polarizability: 18.320269 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 237-239 °C(lit.); 237-240 °C
• Optical Rotation: [α]23/D +58°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (GC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C10H14O3

DETAILS

Sigma Aldrich - 420964

Packaging
1 g in glass bottle
Application
Used to prepare a new chiral oxazolidone auxiliary1 and a ketopinic derivatized polymer used for the deracemization of amines.2 Starting material for the synthesis of homochiral 2,10-camphanediols.3 Employed in the formation of a chiral Schiff base precursor to diethyl (S)-α-amino-α-alkyl phosphonates.4

Sigma Aldrich - 60722

Other Notes
Auxiliary for preparing chiral α-amino alkylphosphonates from imines1,2,3