1-[3,5-bis(trifluoromethyl)phenyl]-3-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methyl]thiourea

• ChemBase ID: 141605
• Molecular Formular: C29H28F6N4OS
• Molecular Mass: 594.6142392
• Monoisotopic Mass: 594.18880186
• SMILES: COc1ccc2c(c1)c(ccn2)[C@@H]([C@@H]1C[C@@H]2CCN1C[C@@H]2C=C)NC(=S)Nc1cc(cc(c1)C(F)(F)F)C(F)(F)F
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](c1ccnc2c1cc(OC)cc2)NC(=S)Nc1cc(cc(c1)C(F)(F)F)C(F)(F)F
• InChI: InChI=1S/C29H28F6N4OS/c1-3-16-15-39-9-7-17(16)10-25(39)26(22-6-8-36-24-5-4-21(40-2)14-23(22)24)38-27(41)37-20-12-18(28(30,31)32)11-19(13-20)29(33,34)35/h3-6,8,11-14,16-17,25-26H,1,7,9-10,15H2,2H3,(H2,37,38,41)/t16-,17-,25-,26-/m0/s1
• InChIKey: IQMKPBFOEWWDIQ-FRSFCCSCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methyl]thiourea
• IUPAC Traditional name: 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methyl]thiourea
• Synonyms: 1-[3,5-Bis(trifluoromethyl)phenyl)-3-{(S)(6-methoxy-4-quinolinyl)-[(2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl]methyl}thiourea; epi-N-Quinyl-N′-bis(3,5-trifluoromethyl)phenylthiourea; N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(8a,9S)-6′-methoxy-9-cinchonanyl]thiourea; 1-[3,5-双(三氟甲基)苯基)-3-{(S)(6-甲氧基-4-喹啉基)-[(2S,4S,5R)-5-乙烯基-1-氮杂-二环[2.2.2]辛-2-基]甲基}硫脲; epi-N-喹啉基-N′-双(3,5-三氟甲基)苯硫脲; N-[3,5-双(三氟甲基)苯基]-N′-[(8a,9S)-6′-甲氧基-9-金鸡宁]硫脲

Database IDs

• CAS Number: 852913-16-7
• MDL Number: MFCD16875670
• PubChem SID: 162235839
• PubChem CID: 11635694

CALCULATED PROPERTIES

• Acid pKa: 9.287586
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8602545
• LogD (pH = 7.4): 5.6135435
• Log P: 6.4556975
• Molar Refractivity: 150.865 cm^3
• Polarizability: 56.79511 Å^3
• Polar Surface Area: 49.42 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]/D -110.0±10.0°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Product Information

• Purity: ≥89.0%; 90%
• Empirical Formula (Hill Notation): C29H28F6N4OS

DETAILS

Sigma Aldrich - 690481

Application
Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.1,2
Packaging
250 mg in glass bottle