2,6-bis[(3aR,8aS)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-yl]pyridine

• ChemBase ID: 140342
• Molecular Formular: C25H19N3O2
• Molecular Mass: 393.43726
• Monoisotopic Mass: 393.14772686
• SMILES: c1ccc2c(c1)C[C@H]1[C@@H]2N=C(O1)c1cccc(n1)C1=N[C@@H]2c3ccccc3C[C@@H]2O1
• Canonical SMILES: c1cc(nc(c1)C1=N[C@H]2[C@@H](O1)Cc1c2cccc1)C1=N[C@H]2[C@@H](O1)Cc1c2cccc1
• InChI: InChI=1S/C25H19N3O2/c1-3-8-16-14(6-1)12-20-22(16)27-24(29-20)18-10-5-11-19(26-18)25-28-23-17-9-4-2-7-15(17)13-21(23)30-25/h1-11,20-23H,12-13H2/t20-,21-,22+,23+/m0/s1
• InChIKey: BZSJUFJXCHHRHW-MYDTUXCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-bis[(3aR,8aS)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-yl]pyridine
• IUPAC Traditional name: 2,6-bis[(3aR,8aS)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-yl]pyridine
• Synonyms: (3aR,8aS)-in-pybox; (3aR,3′aR,8aS,8′aS)-2,2′-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole; 2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine; (3aR,3′aR,8aS,8′aS)-2,2′-(2,6-吡啶二基)双[3a,8a-二氢-8H-茚并[1,2-d]噁唑; 2,6-双[(3aR,8aS)-(+)-8H-茚并[1,2-d]噁唑啉-2-基)吡啶

Database IDs

• CAS Number: 357209-32-6
• MDL Number: MFCD09265074
• PubChem SID: 162234586; 24885191
• PubChem CID: 12170741

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.889827
• LogD (pH = 7.4): 4.9644694
• Log P: 4.9655113
• Molar Refractivity: 112.2403 cm^3
• Polarizability: 43.23614 Å^3
• Polar Surface Area: 56.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 284 °C (dec.)
• Optical Rotation: [α]20/D +386°, c = 1 in methylene chloride(lit.)

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413

Product Information

• Purity: ≥94%
• Empirical Formula (Hill Notation): C25H19N3O2

DETAILS

Sigma Aldrich - 673986

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Catalytic ligand used for:
• [3+2] cycloaddition of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage1
• Enantioselective Mukaiyama-aldol reactions2
• Enantioselective carbonyl-ene reactions3
• Cu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynes4
• Asymmetric three-component coupling reactions catalyzed by a Cu/pybox complex5
• Enantioselective Diels-Alder reaction6
• Ni-catalyzed cross-coupling reactions7