(4S)-4-phenyl-2-{2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl}-4,5-dihydro-1,3-oxazole

• ChemBase ID: 151431
• Molecular Formular: C21H22N2O2
• Molecular Mass: 334.41158
• Monoisotopic Mass: 334.16812795
• SMILES: CC(C)(C1=N[C@H](CO1)c1ccccc1)C1=N[C@H](CO1)c1ccccc1
• Canonical SMILES: CC(C1=N[C@H](CO1)c1ccccc1)(C1=N[C@H](CO1)c1ccccc1)C
• InChI: InChI=1S/C21H22N2O2/c1-21(2,19-22-17(13-24-19)15-9-5-3-6-10-15)20-23-18(14-25-20)16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3/t17-,18-/m1/s1
• InChIKey: JTNVCJCSECAMLD-QZTJIDSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-phenyl-2-{2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl}-4,5-dihydro-1,3-oxazole
• IUPAC Traditional name: (4S)-4-phenyl-2-{2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl}-4,5-dihydro-1,3-oxazole
• Synonyms: (S,S)-2,2′-Isopropylidenebis(4-phenyl-2-oxazoline); (S,S)-2,2-Bis(4-phenyl-2-oxazolin-2-yl)propane; (-)-2,2′-Isopropylidenebis[(4S)-4-phenyl-2-oxazoline]; (S,S)-2,2′-Isopropylidene-bis(4-phenyl-2-oxazoline); (S,S)-2,2-双(4-苯基-2-噁唑啉-2-基)丙烷; (S,S)-2,2′-异亚丙基双(4-苯基-2-噁唑啉); (-)-2,2′-异亚丙基双[(4S)-4-苯基-2-噁唑啉]; (S,S)-2,2′-异亚丙基-双(4-苯基-2-噁唑啉)

Database IDs

• CAS Number: 131457-46-0
• MDL Number: MFCD00192245
• Beilstein Number: 4266906
• PubChem SID: 162245584; 24865286
• PubChem CID: 676388

CALCULATED PROPERTIES

• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.6912336
• LogD (pH = 7.4): 4.6916385
• Log P: 4.6916437
• Molar Refractivity: 96.6745 cm^3
• Polarizability: 37.875736 Å^3
• Polar Surface Area: 43.18 Å^2

PROPERTIES

Physical Property

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 193 °C/0.03 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1 g/mL at 25 °C(lit.)
• Optical Rotation: [α]20/D -150±5°, c = 1% in ethanol; [α]20/D -160°, c = 1 in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (sum of enantiomers, GC); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C21H22N2O2

DETAILS

Sigma Aldrich - 405000

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.1,2,3

Sigma Aldrich - 59429

Other Notes
Chiral ligand; the corresponding metal complexes (Mg, Cu, Fe, etc) catalyze various reactions, e.g. enantioselective Diels-Alder CA1,2; enantioselective cyclopropanation and aziridination reactions3,4