(1R,8R)-11,11-dimethyl-5-oxa-3λ6-thia-4-azatetracyclo[6.2.1.01,6.04,6]undecane-3,3-dione

• ChemBase ID: 146704
• Molecular Formular: C10H15NO3S
• Molecular Mass: 229.296
• Monoisotopic Mass: 229.07726435
• SMILES: CC1([C@@H]2CC[C@]31CS(=O)(=O)N1C3(C2)O1)C
• Canonical SMILES: O=S1(=O)C[C@]23C4(N1O4)C[C@H](C3(C)C)CC2
• InChI: InChI=1S/C10H15NO3S/c1-8(2)7-3-4-9(8)6-15(12,13)11-10(9,5-7)14-11/h7H,3-6H2,1-2H3/t7-,9-,10?,11?/m1/s1
• InChIKey: GBBJBUGPGFNISJ-JRNSMZEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,8R)-11,11-dimethyl-5-oxa-3λ^6-thia-4-azatetracyclo[6.2.1.0^1,^6.0^4,^6]undecane-3,3-dione
• IUPAC Traditional name: (1R,8R)-11,11-dimethyl-5-oxa-3λ^6-thia-4-azatetracyclo[6.2.1.0^1,^6.0^4,^6]undecane-3,3-dione
• Synonyms: (1R)-(-)-(Camphorylsulfonyl)oxaziridine; (1R)-(-)-2,N-Epoxy-exo-10,2-bornanesultam; (1R)-(-)-(10-Camphorsulfonyl)oxaziridine; (1R)-(-)-樟脑磺哑嗪; (1R)-(-)-2,N-环氧基-exo-10,2-莰烷磺内酰胺; (1R)-(-)-(10-樟脑磺)哑嗪

Database IDs

• CAS Number: 104372-31-8
• MDL Number: MFCD00075428
• Beilstein Number: 6274369
• PubChem SID: 24861490; 162240896
• PubChem CID: 16212283

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.0614272
• LogD (pH = 7.4): 1.0614272
• Log P: 1.0614272
• Molar Refractivity: 53.2171 cm^3
• Polarizability: 22.321064 Å^3
• Polar Surface Area: 49.68 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -44°, c = 2.2 in chloroform

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C10H15NO3S

DETAILS

Sigma Aldrich - 349003

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Reactant involved in:
• Asymmetric synthesis of proton pump inhibitors1
• Asymmetric synthesis of polyhydroxylated pyrrolidines2
• Diastereoselective hydroxylation of chlorophylls a and b enolate anions3Used in impregnated silica nanoparticles for removal of sulfur mustard from wastewater4Used to modify blebbistatin for investigations of myosin inhibitor design5