N-hydroxy-N-[(1S,2S)-2-(N-hydroxy-2,2-diphenylacetamido)cyclohexyl]-2,2-diphenylacetamide

• ChemBase ID: 141689
• Molecular Formular: C34H34N2O4
• Molecular Mass: 534.64476
• Monoisotopic Mass: 534.25185758
• SMILES: c1ccc(cc1)C(c1ccccc1)C(=O)N([C@H]1CCCC[C@@H]1N(C(=O)C(c1ccccc1)c1ccccc1)O)O
• Canonical SMILES: ON([C@H]1CCCC[C@@H]1N(C(=O)C(c1ccccc1)c1ccccc1)O)C(=O)C(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C34H34N2O4/c37-33(31(25-15-5-1-6-16-25)26-17-7-2-8-18-26)35(39)29-23-13-14-24-30(29)36(40)34(38)32(27-19-9-3-10-20-27)28-21-11-4-12-22-28/h1-12,15-22,29-32,39-40H,13-14,23-24H2/t29-,30-/m0/s1
• InChIKey: FSKBHXVAXWHEQT-KYJUHHDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxy-N-[(1S,2S)-2-(N-hydroxy-2,2-diphenylacetamido)cyclohexyl]-2,2-diphenylacetamide
• IUPAC Traditional name: N-hydroxy-N-[(1S,2S)-2-(N-hydroxy-2,2-diphenylacetamido)cyclohexyl]-2,2-diphenylacetamide
• Synonyms: (S)-CBHA-DPA; (1S,2S)-N,N′-1,2-cyclohexanediylbis[N-hydroxy-α-phenyl-benzeneacetamide]; (1S,2S)-N,N′-Dihydroxy-N,N′-bis(diphenylacetyl)-cyclohexane-1,2-diamine; (1S,2S)-N,N′-Dihydroxy-N,N′-bis(diphenylacetyl)-1,2-cyclohexanediamine; (1S,2S)-N,N′-二羟基-N,N′-双(二苯基乙酰基)-1,2-环己二胺; (1S,2S)-N,N′-1,2-环己二基双[N-羟基-α-苯基-苯乙酰胺]; (1S,2S)-N,N′-二羟基-N,N′-双(二苯基乙酰基)-环己烷-1,2-二胺

Database IDs

• CAS Number: 1217464-22-6
• MDL Number: MFCD11044410
• PubChem SID: 162235923
• PubChem CID: 44629932

CALCULATED PROPERTIES

• Acid pKa: 7.744353
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 6.6431565
• LogD (pH = 7.4): 6.471003
• Log P: 6.645616
• Molar Refractivity: 155.1516 cm^3
• Polarizability: 60.456707 Å^3
• Polar Surface Area: 81.08 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 199-204 °C
• Optical Rotation: [α]22/D -79.0°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C34H34N2O4

DETAILS

Sigma Aldrich - 700576

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