(4S)-4-benzyl-1,3-oxazolidin-2-one

• ChemBase ID: 149354
• Molecular Formular: C10H11NO2
• Molecular Mass: 177.19984
• Monoisotopic Mass: 177.0789786
• SMILES: c1ccc(cc1)C[C@H]1COC(=O)N1
• Canonical SMILES: O=C1OC[C@@H](N1)Cc1ccccc1
• InChI: InChI=1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m0/s1
• InChIKey: OJOFMLDBXPDXLQ-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-benzyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-benzyl-1,3-oxazolidin-2-one
• Synonyms: (S)-4-Benzyl-2-oxazolidinone; (S)-(-)-4-Benzyl-2-oxazolidinone; (S)-4-Benzyloxazolidin-2-one; (4S)-4-benzyl-1,3-oxazolidin-2-one; (4S)-4-(Phenylmethyl)-2-oxazolidinone; (-)-4-Benzyl-2-oxazolidinone; (4S)-4-(Phenylmethyl)-1,3-oxazolidin-2-one; (4S)-4-Benzyl-1,3-oxazolidin-2-one; (4S)-Benzyloxazolidin-2-one; (S)-4-Benzyl-2-oxazolidinone; (S)-4-苄基-2-噁唑烷酮; (S)-(-)-4-苄基氧氮杂环戊烷酮

Database IDs

• CAS Number: 90719-32-7
• MDL Number: MFCD00064496
• Beilstein Number: 3649667
• PubChem SID: 162243521; 24857725; 24848262
• PubChem CID: 736225

CALCULATED PROPERTIES

• Acid pKa: 13.030782
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.7140553
• LogD (pH = 7.4): 1.7140545
• Log P: 1.7140553
• Molar Refractivity: 48.055 cm^3
• Polarizability: 18.866823 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Crystalline Solid
• Melting Point: 86 - 88°C; 86-88 °C; 86-88 °C(lit.); 86-88°C; 87-89°C
• Optical Rotation: [α]20/D -63°, c = 1 in chloroform; [α]20/D -64±2°, c = 1% in chloroform; -64 (c=1 in chloroform)
• Hydrophobicity(logP): 1.325

Safety Information

• Storage Warning: Hygroscopic
• 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); 95%; 97%; 98%; 99%
• Grade: puriss.
• Optical Purity: ee: 99% (HPLC)
• Empirical Formula (Hill Notation): C10H11NO2

DETAILS

Sigma Aldrich - 294640

Application
Chiral auxiliary for asymmetric alkylation.
Chiral auxiliary used recently in a synthesis of (S)-equol. Preparation and functionalization of chiral, stabilized ylides.
Used for asymmetric synthesis of (3R)- and (3S)-piperazic acid.1
Packaging
25 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - B285825

An oxazolidinone used in chiral auxiliary asymetric synthesis.

REFERENCES

• Evans chiral auxiliary; compare (4S)-(-)-Isopropyl-2-oxazolidinone, A14029.
• For details of use in enantioselective aldol condensation, see: Org. Synth. Coll., 8, 339 (1993):
  
• A simplified method of acylation of the oxazolidinone, avoiding the need for rigorously anhydrous conditions, has been reported using acyl chlorides, anhydrides or pivaloyl mixed anhydrides as the acylating agents catalyzed by DMAP: Synthesis, 1283 (1996).
• See also (4S)-(-)-Isopropyl-2-oxazolidinone, A14029.