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ChemicalBook--->CAS DataBase List--->108448-77-7

108448-77-7

108448-77-7 Structure

108448-77-7 Structure
IdentificationMore
[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 PropertiesBack 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)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
[WGK Germany ]

3
[HS Code ]

29242990
Hazard InformationBack 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.
Spectrum DetailBack Directory
[Spectrum Detail]

(2S)-Bornane-10,2-sultam(108448-77-7)MS
(2S)-Bornane-10,2-sultam(108448-77-7)1HNMR
(2S)-Bornane-10,2-sultam(108448-77-7)13CNMR
(2S)-Bornane-10,2-sultam(108448-77-7)IR1
(2S)-Bornane-10,2-sultam(108448-77-7)IR2
(2S)-Bornane-10,2-sultam(108448-77-7)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

(2S)-Bornane-10,2-sultam, 99+%, (99+% ee)(108448-77-7)
[Alfa Aesar]

(1R,2S)-(+)-10,2-Camphorsultam, 99%(108448-77-7)
[Sigma Aldrich]

108448-77-7(sigmaaldrich)
[TCI AMERICA]

(+)-10,2-Camphorsultam,>97.0%(GC)(108448-77-7)
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