| Identification | More | [Name]
(2S)-Bornane-10,2-sultam | [CAS]
108448-77-7 | [Synonyms]
(+)-10,2-CAMPHORSULTAM
(1R)-(+)-2,10-CAMPHORSULTAM
(1R)-2,10-CAMPHORSULTAM
(1R,2S)-(+)-2,10-CAMPHORSULTAM
(1R,5S)-10,10-DIMETHYL-3-THIA-4-AZATRICYCLO[5.2.1.01,5]DECANE 3,3-DIOXIDE
(+)-2,10-CAMPHORSULTAM
(2S)-BORNANE-10,2-SULTAM
[3AR-(3A-ALPHA,6-ALPHA,7A-BETA)]-HEXAHYDRO-8,8-DIMETHYL-2,2-DIOXIDE-3H-3A,6-METHANO-2,1-BENZISOTHIAZOLE
[3aR-(3aalpha,6alpha,7abeta)]-Hexahydro-8,8-dimethyl-2,2-dioxide-3H-3a,6-methano-2,1-benzisothiazole
(+)-EXO-10,2-BORNANESULTAM
L(+)-10,2-CAMPHORSULTAME
(+)-L-2,10-CAMPHORSULTAM
(1R)-(+)-Camphorsultam
(1R,2S)-(+)-10,2-Camphorsultam
D-(-)-CAMPHOR SULTAM
(+)-2,10-CAMPHORSULTAM 99%
(+)-exo-10,2-Bornanesultam, (1R,5S)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
(+)-10,2-Camphorsultam, (+)-exo-10,2-Bornanesultam, L-2,10-Camphorsultam, (1R,5S)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
(1β,5α,7β)-10,10-Dimethyl-3-thia-4-azatricyclo[5.2.1.01,5]decane3,3-dioxide
(3aR)-1,4,5,6,7,7aβ-Hexahydro-8,8-dimethyl-3H-3aα,6α-methano-2,1-benzisothiazole 2,2-dioxide | [Molecular Formula]
C10H17NO2S | [MDL Number]
MFCD00151762 | [Molecular Weight]
215.31 | [MOL File]
108448-77-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
185-187 °C(lit.)
| [alpha ]
33 º (c=4.9, CHCl3) | [Boiling point ]
324.8±25.0 °C(Predicted) | [density ]
1.1469 (rough estimate) | [refractive index ]
31 ° (C=1, CHCl3) | [storage temp. ]
2-8°C | [solubility ]
almost transparency in Chloroform | [form ]
powder to crystal | [pka]
11.05±0.40(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[α]20/D +32°, c = 5 in chloroform | [BRN ]
4675755 | [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-/m0/s1 | [InChIKey]
DPJYJNYYDJOJNO-CFGJQEBVSA-N | [SMILES]
N1[C@]2([H])[C@@]3(C(C)(C)[C@]([H])(C2)CC3)CS1(=O)=O | [CAS DataBase Reference]
108448-77-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
(1R)-(+)-2,10-Camphorsultam has been used as a reactant in the synthesis of pyrrolidine acid analogs as potent dual PPARα/γ agonists. | [Application]
(2S)-Bornane-10,2-sultam is a pharmaceutical intermediate compound that can be used to synthesize sulfonamide drugs. (2R)-Bornane-10,2-sultam can be used as a chiral auxiliary to perform intramolecular 1,3-dipolar cycloadditions to generate bridged and fused cycloadditions with complete diastereocontrol. Reduction of fused isoxazolidines can generate 1-azaspiro[4.5]decane, which is a potential intermediate in the asymmetric synthesis of cylindrosin alkaloids[1]. | [Purification Methods]
The (-)-enantiomer is recrystallised from 95% EtOH and dried in a vacuum desiccator. It dissolves in dilute aqueous NaOH and can be precipitated without hydrolysis by acidifying. It forms the N-Na salt in EtOH (by addition of Na to the EtOH solution), and the salt can be methylated with MeI to give the (-)-N-Me lactam with m 80o after recrystallisation from hot H2O and has []D -59.6o (c 5, CHCl3) [Shriner et al. J Am Chem Soc 60 2794 1938]. [Oppolzer et al. Helv Chim Acta 69 1142 1986, Weismiller et al. Org Synth 69 154 1955, Beilstein 27 III/IV 1007.] | [References]
[1] MARK C BAGLEY; Wolfgang O. Asymmetric synthesis of 1-azaspiro[4.5]decanes via intramolecular dipolar cycloaddition of nitrones containing the bornane-10,2-sultam chiral auxiliary[J]. Tetrahedron, asymmetry, 2000. DOI:10.1016/S0957-4166(00)00205-6. |
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