(4S)-4-tert-butyl-1,3-oxazolidin-2-one

• ChemBase ID: 147842
• Molecular Formular: C7H13NO2
• Molecular Mass: 143.18362
• Monoisotopic Mass: 143.09462866
• SMILES: CC(C)(C)[C@H]1COC(=O)N1
• Canonical SMILES: CC([C@H]1COC(=O)N1)(C)C
• InChI: InChI=1S/C7H13NO2/c1-7(2,3)5-4-10-6(9)8-5/h5H,4H2,1-3H3,(H,8,9)/t5-/m1/s1
• InChIKey: WKUHGFGTMLOSKM-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-tert-butyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-tert-butyl-1,3-oxazolidin-2-one
• Synonyms: (S)-4-tert-Butyl-2-oxazolidinone; (s)-(-)-4-tert-butyl-2-oxazolidinone; (S)-4-叔丁基-2-噁唑烷酮

Database IDs

• CAS Number: 54705-42-9
• MDL Number: MFCD00221503
• Beilstein Number: 1099836
• PubChem SID: 162242025; 24867604
• PubChem CID: 6950844

CALCULATED PROPERTIES

• Acid pKa: 13.213805
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.323225
• LogD (pH = 7.4): 1.3232244
• Log P: 1.323225
• Molar Refractivity: 36.8297 cm^3
• Polarizability: 14.820513 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 118-120 °C; 118-120 °C(lit.)
• Optical Rotation: [α]20/D +10.5±1°, c = 2% in methylene chloride; [α]21/D -16°, c = 6 in ethanol

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: ≥99.0% (CHN); 97%; 98%; 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C7H13NO2

DETAILS

Sigma Aldrich - 440515

Application
Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta .1
Packaging
1 g in glass bottle

Sigma Aldrich - 20380

Other Notes
Chiral auxiliary used in asymmetric cycloaddition and enolate alkylation reactions. The products are obtained in very high diastereoselectivity1,2,3