1-[2-hydroxy-3-(triphenylsilyl)naphthalen-1-yl]-3-(triphenylsilyl)naphthalen-2-ol

• ChemBase ID: 140847
• Molecular Formular: C56H42O2Si2
• Molecular Mass: 803.10248
• Monoisotopic Mass: 802.27233365
• SMILES: c1ccc(cc1)[Si](c1ccccc1)(c1ccccc1)c1cc2ccccc2c(c1O)c1c2ccccc2cc(c1O)[Si](c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: Oc1c(c2ccccc2cc1[Si](c1ccccc1)(c1ccccc1)c1ccccc1)c1c(O)c(cc2c1cccc2)[Si](c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C56H42O2Si2/c57-55-51(59(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)58)60(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40,57-58H
• InChIKey: STBZSRVMGWTCOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[2-hydroxy-3-(triphenylsilyl)naphthalen-1-yl]-3-(triphenylsilyl)naphthalen-2-ol
• IUPAC Traditional name: 1-[2-hydroxy-3-(triphenylsilyl)naphthalen-1-yl]-3-(triphenylsilyl)naphthalen-2-ol
• Synonyms: (S)-(-)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol; (R)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthalene-2,2′-diol; (R)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol; (S)-(-)-3,3′-双(三苯甲硅烷基)-1,1′-联-2-萘酚; (R)-3,3′-双(三苯甲硅烷基)-1,1′-联萘-2,2′-二酚; (R)-3,3′-双(三苯甲硅烷基)-1,1′-联-2-萘酚

Database IDs

• CAS Number: 111822-69-6
• MDL Number: MFCD09265078
• PubChem SID: 24885546; 162235085; 24885234
• PubChem CID: 394171

CALCULATED PROPERTIES

• Acid pKa: 8.358926
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 13.980401
• LogD (pH = 7.4): 13.935178
• Log P: 13.981
• Molar Refractivity: 239.7348 cm^3
• Polarizability: 101.45769 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 103-145 °C
• Optical Rotation: [α]20/D +114°, c = 1 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C56H42O2Si2

DETAILS

Sigma Aldrich - 680206

Packaging
100 mg in glass bottle

Sigma Aldrich - 674737

Application
Precursor to a chiral Bronsted acid (674745) used to catalyze an enantioselective aza Diels-Alder reaction providing bicyclic lactams.1 Rare earth metal complexes of this chiral binapthol catalyze an intramolecular hydroamination of amino olefins leading to chiral pyrrolidines.2
Packaging
100 mg in glass bottle