2,6-bis[(4S)-4-(2-phenylethyl)-4,5-dihydro-1,3-oxazol-2-yl]pyridine

• ChemBase ID: 142778
• Molecular Formular: C27H27N3O2
• Molecular Mass: 425.52218
• Monoisotopic Mass: 425.21032712
• SMILES: c1ccc(cc1)CC[C@H]1COC(=N1)c1cccc(n1)C1=N[C@H](CO1)CCc1ccccc1
• Canonical SMILES: C([C@H]1COC(=N1)c1cccc(n1)C1=N[C@H](CO1)CCc1ccccc1)Cc1ccccc1
• InChI: InChI=1S/C27H27N3O2/c1-3-8-20(9-4-1)14-16-22-18-31-26(28-22)24-12-7-13-25(30-24)27-29-23(19-32-27)17-15-21-10-5-2-6-11-21/h1-13,22-23H,14-19H2/t22-,23-/m0/s1
• InChIKey: IYRZZMJRGHERQU-GOTSBHOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-bis[(4S)-4-(2-phenylethyl)-4,5-dihydro-1,3-oxazol-2-yl]pyridine
• IUPAC Traditional name: 2,6-bis[(4S)-4-(2-phenylethyl)-4,5-dihydro-1,3-oxazol-2-yl]pyridine
• Synonyms: (S)-BnCH2-PyBox; (S,S)-2,6-Bis(4-benzylmethyl-2-oxazolin-2-yl)pyridine; 2,6-Bis((S)-4,5-dihydro-4-phenethyloxazol-2-yl)pyridine; (S,S)-2,6-双(4-苄基甲基-2-噁唑啉-2-基)吡啶; 2,6-双((S)-4,5-二氢-4-苯乙基噁唑-2-基)吡啶

Database IDs

• CAS Number: 1012042-02-2
• MDL Number: MFCD11656173
• PubChem SID: 162237004
• PubChem CID: 56958442

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 6.149672
• LogD (pH = 7.4): 6.2315073
• Log P: 6.23266
• Molar Refractivity: 124.9927 cm^3
• Polarizability: 48.404 Å^3
• Polar Surface Area: 56.07 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 154-158 °C
• Optical Rotation: [α]22/D -75, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• 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): C27H27N3O2

DETAILS

Sigma Aldrich - 704059

Application
Ligand for asymmetric Negishi cross-coupling of secondary allylic chlorides1
Packaging
1 g in glass bottle
250 mg in glass bottle