1-{2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}-N-[(1R,2R)-2-({2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methanesulfonamido)cyclohexyl]methanesulfonamide

• ChemBase ID: 141110
• Molecular Formular: C26H46N2O6S2
• Molecular Mass: 546.78324
• Monoisotopic Mass: 546.2797292
• SMILES: CC1(C2CCC1(C(C2)O)CS(=O)(=O)N[C@@H]1CCCC[C@H]1NS(=O)(=O)CC12CCC(C1(C)C)CC2O)C
• Canonical SMILES: OC1CC2C(C1(CC2)CS(=O)(=O)N[C@@H]1CCCC[C@H]1NS(=O)(=O)CC12CCC(C2(C)C)CC1O)(C)C
• InChI: InChI=1S/C26H46N2O6S2/c1-23(2)17-9-11-25(23,21(29)13-17)15-35(31,32)27-19-7-5-6-8-20(19)28-36(33,34)16-26-12-10-18(14-22(26)30)24(26,3)4/h17-22,27-30H,5-16H2,1-4H3/t17?,18?,19-,20-,21?,22?,25?,26?/m1/s1
• InChIKey: KVVHJCZXSZVOLS-ODWRNFHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}-N-[(1R,2R)-2-({2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methanesulfonamido)cyclohexyl]methanesulfonamide
• IUPAC Traditional name: 1-{2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}-N-[(1R,2R)-2-({2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methanesulfonamido)cyclohexyl]methanesulfonamide
• Synonyms: N,N′-(1R,2R)-(-)-1,2-cyclohexanediylbis[2-hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-methanesulfonamide]; N,N′-(1R,2R)-(-)-1,2-环己二基双[2-羟基-7,7-二甲基-二环[2.2.1]庚烷-1-甲烷磺酰胺]

Database IDs

• PubChem SID: 24885156; 162235345
• PubChem CID: 12995186

CALCULATED PROPERTIES

• Acid pKa: 9.21096
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.3786283
• LogD (pH = 7.4): 1.372759
• Log P: 1.3787031
• Molar Refractivity: 137.9446 cm^3
• Polarizability: 56.90502 Å^3
• Polar Surface Area: 132.8 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 194-198 °C
• Optical Rotation: [α]20/D -36°, c = 1 in chloroform

Safety Information

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

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C26H46N2O6S2

DETAILS

Sigma Aldrich - 673315

Application
Ligand employed in the titanium-catalyzed vinylation of ketones and enones with vinylzinc reagents.1
Packaging
250 mg in glass bottle