(3aR,8aS)-2-[(3aR,8aS)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-ylmethyl]-3aH,8H,8aH-indeno[1,2-d][1,3]oxazole

• ChemBase ID: 145227
• Molecular Formular: C21H18N2O2
• Molecular Mass: 330.37982
• Monoisotopic Mass: 330.13682783
• SMILES: c1ccc2c(c1)C[C@H]1[C@@H]2N=C(O1)CC1=N[C@@H]2c3ccccc3C[C@@H]2O1
• Canonical SMILES: c1ccc2c(c1)[C@H]1N=C(O[C@H]1C2)CC1=N[C@H]2[C@@H](O1)Cc1c2cccc1
• InChI: InChI=1S/C21H18N2O2/c1-3-7-14-12(5-1)9-16-20(14)22-18(24-16)11-19-23-21-15-8-4-2-6-13(15)10-17(21)25-19/h1-8,16-17,20-21H,9-11H2/t16-,17-,20+,21+/m0/s1
• InChIKey: BDHSVQLSNIGJNC-ZCLUNYJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,8aS)-2-[(3aR,8aS)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-ylmethyl]-3aH,8H,8aH-indeno[1,2-d][1,3]oxazole
• IUPAC Traditional name: (3aR,8aS)-2-[(3aR,8aS)-3aH,8H,8aH-indeno[1,2-d][1,3]oxazol-2-ylmethyl]-3aH,8H,8aH-indeno[1,2-d][1,3]oxazole
• Synonyms: [3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]; [3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-亚甲基双[3a,8a-二氢-8H-茚并[1,2-]噁唑]

Database IDs

• CAS Number: 180186-94-1
• MDL Number: MFCD06797115
• PubChem SID: 24870145; 162239437
• PubChem CID: 1268099

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.7917087
• LogD (pH = 7.4): 3.7919512
• Log P: 3.7919543
• Molar Refractivity: 93.5586 cm^3
• Polarizability: 36.40554 Å^3
• Polar Surface Area: 43.18 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 204-206 °C(lit.)
• Optical Rotation: [α]22/D +353°, c = 3.7 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: 98%
• Empirical Formula (Hill Notation): C21H18N2O2

DETAILS

Sigma Aldrich - 464155

Packaging
500 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