2-(diphenylphosphanyl)-N-[(1S,2S)-2-[2-(diphenylphosphanyl)naphthalene-1-amido]cyclohexyl]naphthalene-1-carboxamide

• ChemBase ID: 140849
• Molecular Formular: C52H44N2O2P2
• Molecular Mass: 790.865482
• Monoisotopic Mass: 790.28780192
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccc2ccccc2c1C(=O)N[C@H]1CCCC[C@@H]1NC(=O)c1c2ccccc2ccc1P(c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(c1c(ccc2c1cccc2)P(c1ccccc1)c1ccccc1)N[C@H]1CCCC[C@@H]1NC(=O)c1c(ccc2c1cccc2)P(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C52H44N2O2P2/c55-51(49-43-29-15-13-19-37(43)33-35-47(49)57(39-21-5-1-6-22-39)40-23-7-2-8-24-40)53-45-31-17-18-32-46(45)54-52(56)50-44-30-16-14-20-38(44)34-36-48(50)58(41-25-9-3-10-26-41)42-27-11-4-12-28-42/h1-16,19-30,33-36,45-46H,17-18,31-32H2,(H,53,55)(H,54,56)/t45-,46-/m0/s1
• InChIKey: VXFKMKXTPXVEMU-ZYBCLOSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diphenylphosphanyl)-N-[(1S,2S)-2-[2-(diphenylphosphanyl)naphthalene-1-amido]cyclohexyl]naphthalene-1-carboxamide
• IUPAC Traditional name: 2-(diphenylphosphanyl)-N-[(1S,2S)-2-[2-(diphenylphosphanyl)naphthalene-1-amido]cyclohexyl]naphthalene-1-carboxamide
• Synonyms: N,N'-((1S,2S)-Cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide); (1S,2S)-(-)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl); (S,S)-DACH-naphthyl Trost Ligand; (1S,2S)-(-)-1,2-二氨基环己烷-N,N′-双(2-二苯基膦-1-萘酰基); (S,S)-DACH-萘基 Trost 配体

Database IDs

• CAS Number: 205495-66-5
• MDL Number: MFCD02684552
• PubChem SID: 162235087
• PubChem CID: 11767928

CALCULATED PROPERTIES

• Acid pKa: 15.284512
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 11.094399
• LogD (pH = 7.4): 11.0944
• Log P: 11.0944
• Molar Refractivity: 238.2108 cm^3
• Polarizability: 94.93485 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 232-237 °C
• Optical Rotation: [α]20/D -66.0°, c = 1 in methanol

Safety Information

• German water hazard class: 3

Product Information

• Purity: 95%; 95+%
• Empirical Formula (Hill Notation): C52H44N2O2P2

DETAILS

Sigma Aldrich - 692786

Application
Asymmetric allylic alkylation ligand.1,2,3,4
Trost Ligands for Asymmetric Allylic Alkylation
Packaging
1 g in glass bottle
250 mg in glass bottle
Legal Information
Sold in collaboration with Dr. Reddy′s Laboratories for research purposes only. US Patent 5739396 applies.