2-(diphenylphosphanyl)-N-[(1S,2S)-2-[2-(diphenylphosphanyl)benzamido]cyclohexyl]benzamide

• ChemBase ID: 130047
• Molecular Formular: C44H40N2O2P2
• Molecular Mass: 690.748122
• Monoisotopic Mass: 690.25650179
• SMILES: O=C(N[C@H]1CCCC[C@@H]1NC(=O)c1ccccc1P(c1ccccc1)c1ccccc1)c1ccccc1P(c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1P(c1ccccc1)c1ccccc1)N[C@H]1CCCC[C@@H]1NC(=O)c1ccccc1P(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m0/s1
• InChIKey: AXMSEDAJMGFTLR-ZAQUEYBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diphenylphosphanyl)-N-[(1S,2S)-2-[2-(diphenylphosphanyl)benzamido]cyclohexyl]benzamide
• IUPAC Traditional name: trost ligand
• Synonyms: Trost's ligand; Trost ligand; (1S,2S)-(-)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphinobenzoyl); (S,S)-DACH-phenyl Trost ligand; (1S,2S)-(-)-1,2-二氨基环己烷-N,N′-双(2-二苯基膦苯甲酰); (S,S)-DACH-苯基 Trost 配体

Database IDs

• CAS Number: 138517-61-0; 169689-05-8
• MDL Number: MFCD01631274
• PubChem SID: 162224332
• PubChem CID: 10963521
• Chemspider ID: 9138733
• Wikipedia Title: Trost_ligand

CALCULATED PROPERTIES

• Acid pKa: 14.919572
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 9.089998
• LogD (pH = 7.4): 9.09
• Log P: 9.09
• Molar Refractivity: 205.3104 cm^3
• Polarizability: 79.7713 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: insoluble; soluble in organic solvents, e.g. acetonitrile, dichloromethane, 1,4-dioxane, methanol, tetrahydrofuran, toluene
• Apperance: white solid
• Melting Point: 136-142 °C
• Optical Rotation: [α]20/D -134°, c = 1 in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C44H40N2O2P2

DETAILS

Sigma Aldrich - 692794

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.