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

• ChemBase ID: 141254
• Molecular Formular: C18H20N4O2
• Molecular Mass: 324.377
• Monoisotopic Mass: 324.1586259
• SMILES: c1ccnc(c1)C(=O)N[C@H]1CCCC[C@@H]1NC(=O)c1ccccn1
• Canonical SMILES: O=C(c1ccccn1)N[C@H]1CCCC[C@@H]1NC(=O)c1ccccn1
• InChI: InChI=1S/C18H20N4O2/c23-17(15-9-3-5-11-19-15)21-13-7-1-2-8-14(13)22-18(24)16-10-4-6-12-20-16/h3-6,9-14H,1-2,7-8H2,(H,21,23)(H,22,24)/t13-,14-/m0/s1
• InChIKey: BVYFDUZVVBXFBQ-KBPBESRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S,2S)-2-(pyridine-2-amido)cyclohexyl]pyridine-2-carboxamide
• IUPAC Traditional name: N-[(1S,2S)-2-(pyridine-2-amido)cyclohexyl]pyridine-2-carboxamide
• Synonyms: (+)-N,N′-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide); (1S,2S)-N,N′-1,2-Cyclohexanediylbis(2-pyridinecarboxamide); (1S,2S)-(+)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane; (1S,2S)-1,2-Bis(2-pyridinecarboxamido)cyclohexane; (S,S)-DACH-pyridyl Trost ligand; (+)-N,N′-(1S,2S)-1,2-二氨基环己烷二基双(2-吡啶甲酰胺); (1S,2S)-1,2-双(2-吡啶碳酰胺)环己烷; (1S,2S)-N,N′-1,2-环己烷二基双(2-吡啶甲酰胺); (1S,2S)-(+)-1,2-双[(2-吡啶基羰基)氨基]环己烷; (S,S)-DACH-吡啶基 Trost 配体

Database IDs

• CAS Number: 172138-95-3
• MDL Number: MFCD02684544
• PubChem SID: 24885381; 162235489
• PubChem CID: 9831204

CALCULATED PROPERTIES

• Acid pKa: 14.363248
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.67439
• LogD (pH = 7.4): 1.6744237
• Log P: 1.6744242
• Molar Refractivity: 89.1228 cm^3
• Polarizability: 34.136337 Å^3
• Polar Surface Area: 83.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 171-176 °C
• Optical Rotation: [α]20/D +98°, c = 1 in methanol

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97%
• Empirical Formula (Hill Notation): C18H20N4O2

DETAILS

Sigma Aldrich - 692743

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

Sigma Aldrich - 677531

Application
Trost Ligands for Asymmetric Allylic Alkylation