|
|
| | (2S)-Bornane-10,2-sultam Basic information |
| Product Name: | (2S)-Bornane-10,2-sultam | | Synonyms: | (7aS)-8,8-Dimethylhexahydro-1H-3a,6-methanobenzo[c]isothiazole 2,2-dioxide;(2S)-Borne-10,2-sultam;L-2,10-Camphorsultam,99%e.e.;(2S)-BORNANE-10,2-SULTAM;(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 | | CAS: | 108448-77-7 | | MF: | C10H17NO2S | | MW: | 215.31 | | EINECS: | | | Product Categories: | chiral;Asymmetric Synthesis;Bicyclic Monoterpenes;Biochemistry;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Terpenes;Peptide | | Mol File: | 108448-77-7.mol |  |
| | (2S)-Bornane-10,2-sultam Chemical Properties |
| 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. | Sealed in dry,Room Temperature | | solubility | almost transparency in Chloroform | | pka | 11.05±0.40(Predicted) | | form | powder to crystal | | 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 Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | HS Code | 29242990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (2S)-Bornane-10,2-sultam Usage And Synthesis |
| 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. |
| | (2S)-Bornane-10,2-sultam Preparation Products And Raw materials |
|