N-[(1S,2S)-2-[2,2-bis(3,5-dimethylphenyl)-N-hydroxyacetamido]cyclohexyl]-2,2-bis(3,5-dimethylphenyl)-N-hydroxyacetamide

• ChemBase ID: 142712
• Molecular Formular: C42H50N2O4
• Molecular Mass: 646.8574
• Monoisotopic Mass: 646.37705809
• SMILES: Cc1cc(cc(c1)C(c1cc(cc(c1)C)C)C(=O)N([C@H]1CCCC[C@@H]1N(C(=O)C(c1cc(cc(c1)C)C)c1cc(cc(c1)C)C)O)O)C
• Canonical SMILES: ON([C@H]1CCCC[C@@H]1N(C(=O)C(c1cc(C)cc(c1)C)c1cc(C)cc(c1)C)O)C(=O)C(c1cc(C)cc(c1)C)c1cc(C)cc(c1)C
• InChI: InChI=1S/C42H50N2O4/c1-25-13-26(2)18-33(17-25)39(34-19-27(3)14-28(4)20-34)41(45)43(47)37-11-9-10-12-38(37)44(48)42(46)40(35-21-29(5)15-30(6)22-35)36-23-31(7)16-32(8)24-36/h13-24,37-40,47-48H,9-12H2,1-8H3/t37-,38-/m0/s1
• InChIKey: UXJIDQVUTGVBNI-UWXQCODUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S,2S)-2-[2,2-bis(3,5-dimethylphenyl)-N-hydroxyacetamido]cyclohexyl]-2,2-bis(3,5-dimethylphenyl)-N-hydroxyacetamide
• IUPAC Traditional name: N-[(1S,2S)-2-[2,2-bis(3,5-dimethylphenyl)-N-hydroxyacetamido]cyclohexyl]-2,2-bis(3,5-dimethylphenyl)-N-hydroxyacetamide
• Synonyms: (S)-CBHA-DMDA; (1S,2S)-N,N′-Dihydroxy-N,N′-bis(3,5-dimethyldiphenylacetyl)-cyclohexane-diamine; N,N′-(1S,2S)-1,2-cyclohexanediylbis[α-(3,5-dimethylphenyl)-N-hydroxy-3,5-dimethylbenzeneacetamide]; (1S,2S)-N,N′-Dihydroxy-N,N′-bis(bis(3,5-dimethylphenyl)acetyl)-1,2-cyclohexanediamine; (1S,2S)-N,N′-二羟基-N,N′-双(3,5-二甲基二苯基乙酰基)-环己烷-二胺; N,N′-(1S,2S)-1,2-环己二基双[α-(3,5-二甲苯基)-N-羟基-3,5-二甲基苯乙酰胺]; (1S,2S)-N,N′-二羟基-N,N′-双(双(3,5-二甲苯基)乙酰基)-1,2-环己二胺

Database IDs

• CAS Number: 1217463-44-9
• PubChem SID: 162236938
• PubChem CID: 71310779

CALCULATED PROPERTIES

• Acid pKa: 7.7443495
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 10.750527
• LogD (pH = 7.4): 10.578373
• Log P: 10.752987
• Molar Refractivity: 195.4812 cm^3
• Polarizability: 74.58211 Å^3
• Polar Surface Area: 81.08 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 186-190 °C
• Optical Rotation: [α]22/D -76°, 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): C42H50N2O4

DETAILS

Sigma Aldrich - 700568

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