(1S,5R,7R)-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-3,3-dione

• ChemBase ID: 147484
• Molecular Formular: C10H17NO2S
• Molecular Mass: 215.31248
• Monoisotopic Mass: 215.09799979
• SMILES: CC1([C@@H]2CC[C@@]31CS(=O)(=O)N[C@@H]3C2)C
• Canonical SMILES: O=S1(=O)N[C@H]2[C@]3(C1)CC[C@H](C2)C3(C)C
• InChI: InChI=1S/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3/t7-,8-,10-/m1/s1
• InChIKey: DPJYJNYYDJOJNO-NQMVMOMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,7R)-10,10-dimethyl-3λ^6-thia-4-azatricyclo[5.2.1.0^1,^5]decane-3,3-dione
• IUPAC Traditional name: (1S,5R,7R)-10,10-dimethyl-3λ^6-thia-4-azatricyclo[5.2.1.0^1,^5]decane-3,3-dione
• Synonyms: (-)-10,2-Camphorsultam; (-)-exo-10,2-Bornanesultam; (1S,5R)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide; [3aS-(3aα,6α,7aβ)]-hexahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazole-2,2-dioxide; (1S)-(-)-2,10-Camphorsultam; (-)-10,2-Camphorsultam; (-)-10,2-樟脑磺内酰胺; (-)-exo-10,2-莰烷磺内酰胺; (1S,5R)-10,10-二甲基-3-硫杂-4-氮杂三环[5.2.1.01,5]癸烷-3,3-二氧化物; [3aS-(3aα,6α,7aβ)]-六氢-8,8-二甲基-3H-3a,6-亚甲基-2,1-苯并异噻唑基-2,2-二氧化物; (1S)-(-)-2,10-樟脑磺内酰胺; (-)-10,2-樟脑磺内酰胺

Database IDs

• CAS Number: 94594-90-8
• MDL Number: MFCD00066271
• Beilstein Number: 83811
• PubChem SID: 24857980; 24852794; 162241672
• PubChem CID: 854020

CALCULATED PROPERTIES

• Acid pKa: 10.407443
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.5864519
• LogD (pH = 7.4): 0.5860786
• Log P: 0.58645666
• Molar Refractivity: 53.6538 cm^3
• Polarizability: 22.299479 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 181-183 °C(lit.); 183-185 °C
• Optical Rotation: [α]19/D -32°, c = 5 in chloroform; [α]20/D -33±1°, c = 1% in ethanol

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: ≥98.0% (GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C10H17NO2S

DETAILS

Sigma Aldrich - 298352

Packaging
5 g in glass bottle

Sigma Aldrich - 21372

Other Notes
Chiral auxiliary used to prepare N-acryloyl derivatives which are employed as dienophiles in asymmetric Diels-Alder reactions 1; and for other asymmetric transformations 2,3