(S,S)-DACH-pyridyl Trost ligand
(+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide)
CAS: 172138-95-3
Molecular Formula: C18H20N4O2
(S,S)-DACH-pyridyl Trost ligand - Names and Identifiers
| Name | (+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide) |
| Synonyms | (S,S)-DACH-pyridyl Trost ligand 2,6-Bis[(4S)-benzyl-2-oxazolin-2-yl]-pyridine N-((1S,2S)-2-(picolinamido)cyclohexyl)picolinamide N,N'-(1S,2S)-cyclohexane-1,2-diyldipyridine-2-carboxamide (1R,2R)-(-)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane 1S,2S- N,N'-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide) (+)-N,N'-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide) (1S,2S)-N,Nμ-1,2-Cyclohexanediylbis(2-pyridinecarboxamide), (+)-N,Nμ-(1S,2S)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide), (1S,2S)-(+)-1,2-Bis[(2-pyridinylcarbonyl)amino]cyclohexane, (1S,2S)-1,2-Bis(2-pyridinecarboxamido)cyclohexane |
| CAS | 172138-95-3 |
| InChI | InChI=1/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 |
(S,S)-DACH-pyridyl Trost ligand - Physico-chemical Properties
| Molecular Formula | C18H20N4O2 |
| Molar Mass | 324.38 |
| Density | 1.25±0.1 g/cm3(Predicted) |
| Melting Point | 170°C |
| Boling Point | 663.4±50.0 °C(Predicted) |
| Specific Rotation(α) | +95° (c 1, CH3OH) |
| Flash Point | 354.991°C |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | Powder |
| Color | off-white |
| pKa | 12.51±0.40(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.61 |
(S,S)-DACH-pyridyl Trost ligand - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
(S,S)-DACH-pyridyl Trost ligand - Reference Information
| preparation | adding 1,1 '-carbonyldiimidazole (1.7Kg,10.48mol) and THF(7.5L) to a 22L flask, adding solid pyridine formic acid (1.36Kg,11mol) to the slurry at room temperature, reacting endotherms, cooling the mixture from 18 ℃ to 12 ℃, the reaction mixture was then heated to 18-19°C. Stir the clarified solution for 1 hour and add (1S,2S)-( )-1,2-diaminocyclohexane (0.5Kg,4.38mol) within 1 hour while keeping the temperature below 50 ℃, rinse the beaker and funnel with 2.5L THF, stir the reaction at room temperature for 15 hours, add water (0.5L) to the slurry to obtain a clarified solution, the reaction mixture is stirred for 1 hour, the reaction mixture is concentrated into an orange semi-solid by rotary evaporation, the reaction product is slurped in 5L ethanol and concentrated by rotary evaporation, dissolved in ethanol (5L) at 64-65°C, cooled, The solution becomes turbid at about 58°C. At this temperature, the turbid solution was inoculated (10g) and cooled to -8°C. The resulting white crystals were separated by filtration on a sintered glass funnel and washed with 5L cold water. Ethanol (-8 to -10°C), purged with nitrogen under indoor vacuum, and then dried in a vacuum oven (35°C). This resulted in the separation of 1.23Kg(86.3%) white crystalline solids. |
| Use | Ligands for asymmetric allylation reactions. |
Last Update：2024-04-09 15:16:48
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