3-{[(1R,2R)-2-(piperidin-1-yl)cyclohexyl]amino}-4-{[4-(trifluoromethyl)phenyl]amino}cyclobutane-1,2-dione

• ChemBase ID: 143317
• Molecular Formular: C22H28F3N3O2
• Molecular Mass: 423.4718296
• Monoisotopic Mass: 423.21336181
• SMILES: c1cc(ccc1C(F)(F)F)NC1C(C(=O)C1=O)N[C@@H]1CCCC[C@H]1N1CCCCC1
• Canonical SMILES: O=C1C(=O)C(C1Nc1ccc(cc1)C(F)(F)F)N[C@@H]1CCCC[C@H]1N1CCCCC1
• InChI: InChI=1S/C22H28F3N3O2/c23-22(24,25)14-8-10-15(11-9-14)26-18-19(21(30)20(18)29)27-16-6-2-3-7-17(16)28-12-4-1-5-13-28/h8-11,16-19,26-27H,1-7,12-13H2/t16-,17-,18?,19?/m1/s1
• InChIKey: OGZKYKUCJLBYBG-YYZRRKBYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1R,2R)-2-(piperidin-1-yl)cyclohexyl]amino}-4-{[4-(trifluoromethyl)phenyl]amino}cyclobutane-1,2-dione
• IUPAC Traditional name: 3-{[(1R,2R)-2-(piperidin-1-yl)cyclohexyl]amino}-4-{[4-(trifluoromethyl)phenyl]amino}cyclobutane-1,2-dione
• Synonyms: 3-{[(1R,2R)-2-(1-Piperidinyl)cyclohexyl]amino}-4-{[4-(trifluoromethyl)phenyl]amino}-3-cyclobutene-1,2-dione; Rawal Squaramide Organocatalyst; N-[(1R,2R)-2-(1-Piperidinyl)cyclohexyl]-N′-[4-(trifluoromethyl)phenyl]squaramide

Database IDs

• CAS Number: 1211565-08-0
• MDL Number: MFCD18827464
• PubChem SID: 162237538
• PubChem CID: 71310923

CALCULATED PROPERTIES

• Acid pKa: 8.525341
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9812741
• LogD (pH = 7.4): 3.6723988
• Log P: 3.9225051
• Molar Refractivity: 109.1076 cm^3
• Polarizability: 41.138172 Å^3
• Polar Surface Area: 61.44 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -42.0±2.0°, c = 1 in DMSO

Safety Information

• European Hazard Symbols: Corrosive (C)
• German water hazard class: 3
• Risk Statements: 37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338

Product Information

• Purity: ≥94.5% (HPLC); 95%
• Impurities: ≤2.0% pyridine
• Empirical Formula (Hill Notation): C22H26F3N3O2

DETAILS

Sigma Aldrich - 728357

Application
Catalyst for enantioselective Michael addition1.