2-[(4S)-4-phenyl-1,3-oxazolidin-2-ylidene]-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile

• ChemBase ID: 147284
• Molecular Formular: C20H17N3O2
• Molecular Mass: 331.36788
• Monoisotopic Mass: 331.1320768
• SMILES: c1ccc(cc1)[C@H]1CO/C(=C(/C#N)\C2=N[C@H](CO2)c2ccccc2)/N1
• Canonical SMILES: N#C/C(=C\1/OC[C@@H](N1)c1ccccc1)/C1=N[C@H](CO1)c1ccccc1
• InChI: InChI=1S/C20H17N3O2/c21-11-16(19-22-17(12-24-19)14-7-3-1-4-8-14)20-23-18(13-25-20)15-9-5-2-6-10-15/h1-10,17-18,22H,12-13H2/t17-,18-/m1/s1
• InChIKey: QVVGSAYHUSBCQV-QZTJIDSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4S)-4-phenyl-1,3-oxazolidin-2-ylidene]-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile
• IUPAC Traditional name: 2-[(4S)-4-phenyl-1,3-oxazolidin-2-ylidene]-2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]acetonitrile
• Synonyms: (S,S)-4-Phenyl-α-(4-phenyloxazolidin-2-ylidene)-2-oxazoline-2-acetonitrile; (4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile; (S,S)-4-苯基-α-(4-苯基噁唑烷-2-亚基)-2-噁唑啉-2-乙腈; (4S)-(+)-苯基-α-[(4S)-苯基噁唑烷-2-亚基]-2-噁唑啉-2-乙腈

Database IDs

• CAS Number: 150639-33-1
• MDL Number: MFCD00192394
• PubChem SID: 24866118; 162241474
• PubChem CID: 22831470

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.748297
• LogD (pH = 7.4): 3.7486265
• Log P: 3.7486308
• Molar Refractivity: 103.4039 cm^3
• Polarizability: 36.03704 Å^3
• Polar Surface Area: 66.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 146-148 °C(lit.)
• Optical Rotation: [α]20/D +364°, 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: 97%
• Empirical Formula (Hill Notation): C20H17N3O2

DETAILS

Sigma Aldrich - 417068

Packaging
1 g in glass bottle
Application
Ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.1,2,3