N-(3,5-dimethylphenyl)-N-[(1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]benzenesulfonamide

• ChemBase ID: 139268
• Molecular Formular: C24H31NO3S
• Molecular Mass: 413.57284
• Monoisotopic Mass: 413.20246486
• SMILES: Cc1cc(cc(c1)N([C@@H]1[C@H]2CC[C@@]([C@@H]1O)(C2(C)C)C)S(=O)(=O)c1ccccc1)C
• Canonical SMILES: Cc1cc(C)cc(c1)N(S(=O)(=O)c1ccccc1)[C@H]1[C@@H](O)[C@]2(C([C@@H]1CC2)(C)C)C
• InChI: InChI=1S/C24H31NO3S/c1-16-13-17(2)15-18(14-16)25(29(27,28)19-9-7-6-8-10-19)21-20-11-12-24(5,22(21)26)23(20,3)4/h6-10,13-15,20-22,26H,11-12H2,1-5H3/t20-,21-,22-,24+/m1/s1
• InChIKey: XOYOZKHVKVMVIE-AZKZNFPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3,5-dimethylphenyl)-N-[(1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]benzenesulfonamide
• IUPAC Traditional name: N-(3,5-dimethylphenyl)-N-[(1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]benzenesulfonamide
• Synonyms: (1R,2S,3R)-(+)-3-[N-Benzenesulfonyl-N-(3,5-dimethylphenyl)amino]-2-bornanol; (1R,exo,exo)-3-[N-(3,5-Dimethylphenyl)benzenesulfonamido]isoborneol; (1R,2S,3R)-(+)-3-[N-苯磺酰基-N-(3,5-二甲基苯基)氨基]-2-莰醇; (1R,外,外)-3-[N-(3,5-二甲基苯基)苯亚磺酰氨基]异冰片

Database IDs

• CAS Number: 87420-26-6
• MDL Number: MFCD00078990
• Beilstein Number: 4715153
• PubChem SID: 24865881; 162233516
• PubChem CID: 10884167

CALCULATED PROPERTIES

• Acid pKa: 14.054308
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.222515
• LogD (pH = 7.4): 5.222515
• Log P: 5.222515
• Molar Refractivity: 116.2068 cm^3
• Polarizability: 46.291573 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 122-125 °C; 122-125 °C(lit.)
• Optical Rotation: [α]20/D +65±2°, c = 4% in chloroform; [α]20/D +65°, c = 4 in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: ≥98.5% (sum of enantiomers, HPLC); 99%
• Empirical Formula (Hill Notation): C24H31NO3S

DETAILS

Sigma Aldrich - 41390

Other Notes
Auxiliary for very efficient asymmetric reactions: asymmetric alkylation of its esters1; asymmetric conjugate addition to its enoates2,3; hydroxylation of its esters4

Sigma Aldrich - 309613

Packaging
250 mg in glass bottle