N-hydroxy-N-[(1R,2R)-2-(N-hydroxy-3,3,3-triphenylpropanamido)cyclohexyl]-3,3,3-triphenylpropanamide

• ChemBase ID: 142710
• Molecular Formular: C48H46N2O4
• Molecular Mass: 714.88984
• Monoisotopic Mass: 714.34575796
• SMILES: c1ccc(cc1)C(CC(=O)N([C@@H]1CCCC[C@H]1N(C(=O)CC(c1ccccc1)(c1ccccc1)c1ccccc1)O)O)(c1ccccc1)c1ccccc1
• Canonical SMILES: ON([C@@H]1CCCC[C@H]1N(C(=O)CC(c1ccccc1)(c1ccccc1)c1ccccc1)O)C(=O)CC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C48H46N2O4/c51-45(35-47(37-21-7-1-8-22-37,38-23-9-2-10-24-38)39-25-11-3-12-26-39)49(53)43-33-19-20-34-44(43)50(54)46(52)36-48(40-27-13-4-14-28-40,41-29-15-5-16-30-41)42-31-17-6-18-32-42/h1-18,21-32,43-44,53-54H,19-20,33-36H2/t43-,44-/m1/s1
• InChIKey: VWHFLRGVWVBFFY-NDOUMJCMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxy-N-[(1R,2R)-2-(N-hydroxy-3,3,3-triphenylpropanamido)cyclohexyl]-3,3,3-triphenylpropanamide
• IUPAC Traditional name: N-hydroxy-N-[(1R,2R)-2-(N-hydroxy-3,3,3-triphenylpropanamido)cyclohexyl]-3,3,3-triphenylpropanamide
• Synonyms: (R)-CBHA-TPP; (1R,2R)-N,N′-Dihydroxy-N,N′-bis(triphenylpropionyl)-cyclohexane-1,2-diamine; N,N′-(1R,2R)-1,2-cyclohexanediylbis[N-hydroxy-β,β-diphenylbenzenepropanamide]; (1R,2R)-N,N′-Dihydroxy-N,N′-bis(3,3,3-triphenylpropionyl)-1,2-cyclohexanediamine; (1R,2R)-N,N′-二羟基-N,N′-双(三苯基丙酰)-1,2-环己二胺; N,N′-(1R,2R)-1,2-环己二基双[N-羟基-β,β-二苯基苯丙酰胺]; (1R,2R)-N,N′-二羟基-N,N′-双(3,3,3-三苯基丙酰)-环己烷-1,2-二胺

Database IDs

• CAS Number: 860036-29-9
• MDL Number: MFCD11044407
• PubChem SID: 162236936
• PubChem CID: 11354564

CALCULATED PROPERTIES

• Log P: 9.890521
• Molar Refractivity: 215.1982 cm^3
• Polarizability: 83.38486 Å^3
• Polar Surface Area: 81.08 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false
• Acid pKa: 7.801597
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 9.888365
• LogD (pH = 7.4): 9.735559

PROPERTIES

Physical Property

• Melting Point: 217-221 °C
• Optical Rotation: [α]22/D +22.0±5°, c = 1 in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C48H46N2O4

DETAILS

Sigma Aldrich - 700541

Application
Ligand used with vanadium for asymmetric epoxidation of allylic alcohols1,2
Packaging
50 mg in glass bottle
Protocols & Applications
Asymmetric Oxidation with CHBA Ligands
Asymmetric Epoxidation of Allylic Alcohols
Asymmetric Epoxidation of Homoallylic Alcohols
Asymmetric Ketone Hydrogenation
Asymmetric Transfer Hydrogenation