(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

• ChemBase ID: 92245
• Molecular Formular: C6H11NO2
• Molecular Mass: 129.15704
• Monoisotopic Mass: 129.0789786
• SMILES: N1[C@H](COC1=O)C(C)C
• Canonical SMILES: CC([C@H]1COC(=O)N1)C
• InChI: InChI=1S/C6H11NO2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m1/s1
• InChIKey: YBUPWRYTXGAWJX-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-isopropyl-1,3-oxazolidin-2-one
• Synonyms: (S)-(-)-4-Isopropyl-2-oxazolidinone; (S)-4-Isopropyl-2-oxazolidinone; 4(S)-(1-Methylethyl)-2-oxazolidinone; 4(S)-Isopropyloxazolidin-2-one; (S)-(-)-4-Isopropyl-2-oxazolidinone; (4s)-(-)-4-isopropyl-2-oxazolidinone; (4S)-(-)-Isopropyl-2-oxazolidinone; (4R)-4-Isopropyl-1,3-oxazolidin-2-one; (S)-(-)-4-异丙基-2-噁唑烷酮; (4S)-(-)-异丙基-2-恶唑啉酮

Database IDs

• CAS Number: 95530-58-8; 17016-83-0
• MDL Number: MFCD00075172; MFCD00010847
• Beilstein Number: 3588198
• PubChem SID: 24858002; 24881639; 162078943
• PubChem CID: 7157133

CALCULATED PROPERTIES

• Acid pKa: 13.160297
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.94522417
• LogD (pH = 7.4): 0.9452235
• Log P: 0.94522417
• Molar Refractivity: 32.4316 cm^3
• Polarizability: 12.991205 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol
• Apperance: White to off-White Solid
• Melting Point: 70-72°C; 70-73 °C; 70-73 °C(lit.); 70-73°C; 70-74°C
• Optical Rotation: [α]20/D +14±1°, c = 7% in chloroform; [α]20/D -18°, c = 6 in ethanol; -17 (c=6 in ethanol)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 98%; 99%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C6H11NO2

DETAILS

Sigma Aldrich - 298883

Application
Reagent employed as a chiral ligand in dirhodium(II) complexes1 and as a chiral auxiliary in aldol addition reactions.2 Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta.3
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 59660

Other Notes
The 3-acyl derivatives are used in many enantioselective reactions: the 3-propionyl derivative in aldol reactions1,2,3; and alkylations4

REFERENCES

• Alkyl carboxamides derived from the N-acylation of the oxazolidinone form enolates which undergo highly enantioselective aldol condensation with aldehydes. The products readily undergo hydrolysis, e.g. with base, to give chiral ? -hydroxyacids, with consequent easy recovery and recycle of the chiral auxiliary: J. Am. Chem. Soc., 103, 2127 (1981); Tetrahedron, 27, 897 (1986); Tetrahedron Lett., 31, 4699 (1990); J. Org. Chem., 56, 2489 (1991). For reaction scheme, see (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.
• The enolates of the N-acyloxazolidinones can also undergo a variety of other enantioselective reactions including alkylation: J. Am. Chem. Soc., 104, 1737 (1982); acylation: J. Am. Chem. Soc., 106, 1154 (1984):
  
• Bromination (NBS), followed by azide displacement, gives a route to chiral amino acids: Tetrahedron Lett ., 28, 1123 (1987). Direct electrophilic azidation with triisopropylbenzenesulfonyl azide has also been used to effect this transformation: J. Am. Chem. Soc., 112, 4011 (1990).
• Chiral auxiliary introduced by Evans for use in enantioselective reactions.
• See also (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.