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

• ChemBase ID: 77305
• Molecular Formular: C9H15NO3
• Molecular Mass: 185.2203
• Monoisotopic Mass: 185.10519335
• SMILES: N1(C(=O)CC)[C@H](COC1=O)C(C)C
• Canonical SMILES: CCC(=O)N1C(=O)OC[C@@H]1C(C)C
• InChI: InChI=1S/C9H15NO3/c1-4-8(11)10-7(6(2)3)5-13-9(10)12/h6-7H,4-5H2,1-3H3/t7-/m1/s1
• InChIKey: HOWPHXVPNNPSAZ-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-(propan-2-yl)-3-propanoyl-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-isopropyl-3-propanoyl-1,3-oxazolidin-2-one
• Synonyms: (R)-4-Isopropyl-3-propionyloxazolidin-2-one; (S)-4-Isopropyl-3-propionyl-2-oxazolidinone; (S)-3-Propionyl-4-isopropyl-2-oxazolidinone; (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone; (s)-(+)-4-isopropyl-3-propionyl-2-oxazolidinone; (S)-4-异丙基-3-丙酰基-2-噁唑烷酮; (S)-3-丙酰基-4-异丙基-2-噁唑烷酮; (S)-(+)-4-异丙基-3-丙酰基-2-噁唑烷酮

Database IDs

• CAS Number: 77877-19-1
• MDL Number: MFCD00043401; MFCD00269691
• Beilstein Number: 3542849
• PubChem SID: 24860302; 24881688; 162042178
• PubChem CID: 853160

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6343683
• LogD (pH = 7.4): 1.6343683
• Log P: 1.6343683
• Molar Refractivity: 46.6244 cm^3
• Polarizability: 18.603695 Å^3
• Polar Surface Area: 46.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 102-106 °C/0.75 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.094 g/mL at 20 °C(lit.); 1.094 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.464(lit.); n20/D 1.465
• Optical Rotation: [α]20/D +94±2°, c = 8.7% in methylene chloride; [α]25/D +93°, c = 8.7 in methylene chloride

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (sum of enantiomers, GC); 97%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C9H15NO3

DETAILS

Sigma Aldrich - 335304

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

Sigma Aldrich - 59735

Other Notes
Chiral derivative of propionic acid used in highly enantioselective aldol, alkylation and acylation reactions1,2,3,4,5