(4R)-2-[2-(diphenylphosphanyl)phenyl]-4-(propan-2-yl)-4,5-dihydro-1,3-oxazole

• ChemBase ID: 88671
• Molecular Formular: C24H24NOP
• Molecular Mass: 373.427221
• Monoisotopic Mass: 373.15955102
• SMILES: N1=C(c2c(cccc2)P(c2ccccc2)c2ccccc2)OC[C@H]1C(C)C
• Canonical SMILES: CC([C@@H]1COC(=N1)c1ccccc1P(c1ccccc1)c1ccccc1)C
• InChI: InChI=1S/C24H24NOP/c1-18(2)22-17-26-24(25-22)21-15-9-10-16-23(21)27(19-11-5-3-6-12-19)20-13-7-4-8-14-20/h3-16,18,22H,17H2,1-2H3/t22-/m0/s1
• InChIKey: OUQSAXROROGQEE-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-2-[2-(diphenylphosphanyl)phenyl]-4-(propan-2-yl)-4,5-dihydro-1,3-oxazole
• IUPAC Traditional name: (4R)-2-[2-(diphenylphosphanyl)phenyl]-4-isopropyl-4,5-dihydro-1,3-oxazole
• Synonyms: (-)(4S)-2-[2-(Diphenylphosphino)phenyl]-4-(2-propyl)oxazoline 97%; (R)-(+)-2-[2-(Diphenylphosphino)phenyl]-4,5-dihydro-4-isopropyl-oxazole; (R)-(+)-2-[2-(Diphenylphosphino)phenyl]-4-isopropyl-2-oxazoline; (R)-(+)-2-[2-(二苯基膦)苯基]-4,5-二氢-4-异丙基-噁唑; (R)-(+)-2-[2-(二苯基膦)苯基]-4-异丙基-2-噁唑啉

Database IDs

• CAS Number: 164858-78-0; 148461-14-7
• MDL Number: MFCD03427599; MFCD02684553
• Beilstein Number: 8156604
• PubChem SID: 162075592; 24886425
• PubChem CID: 2734144

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.0686517
• LogD (pH = 7.4): 6.0795593
• Log P: 6.0797
• Molar Refractivity: 112.3163 cm^3
• Polarizability: 44.00227 Å^3
• Polar Surface Area: 21.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 85-90 °C
• Optical Rotation: [α]20/D +48±3°, c = 1.4% in chloroform

Safety Information

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

Product Information

• Purity: ≥97.0% (CHN)
• Empirical Formula (Hill Notation): C24H24NOP

DETAILS

Sigma Aldrich - 72575

Other Notes
Asymmetric alkylation with an iridium catalyst1; Chiral ligand for asymmetric reduction reaction2
Packaging
100, 500 mg in glass bottle