(2R)-Bornane-10,2-sultam
Synonym(s):(−)-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
- CAS NO.:94594-90-8
- Empirical Formula: C10H17NO2S
- Molecular Weight: 215.31
- MDL number: MFCD00066271
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-27 20:28:20
What is (2R)-Bornane-10,2-sultam?
Chemical properties
white to light yellow crystal powde
The Uses of (2R)-Bornane-10,2-sultam
(2R)-Bornane-10,2-sultam is a reagent used to make Camphorsultam conjugates.
The Uses of (2R)-Bornane-10,2-sultam
(1S,2R)-(-)-10,2-Camphorsultam is used in the asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine. It is used as proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones. It is also employed as a chiral probe for the optical resolution by HPLC and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids. Also used to prepare N-acryloyl derivatives which are employed as dienophiles in asymmetric Diels-Alder reactions. and for other asymmetric transformations.
The Uses of (2R)-Bornane-10,2-sultam
(1S)-(?)-2,10-Camphorsultam may be used in the asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine. It may be used as proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones.
General Description
(1S,2R,4R)-(?)-2,10-Camphorsultam may be employed as a chiral probe for the optical resolution by HPLC and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids.
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.]
Properties of (2R)-Bornane-10,2-sultam
Melting point: | 183-185 °C |
Boiling point: | 324.8±25.0 °C(Predicted) |
alpha | -33 º (c=4.9, CHCl3) |
Density | 1.1469 (rough estimate) |
refractive index | -31 ° (C=1, CHCl3) |
storage temp. | Sealed in dry,Room Temperature |
solubility | Chloroform, Ethanol, Methanol |
form | Liquid |
pka | 11.05±0.40(Predicted) |
color | Clear colorless |
optical activity | [α]19/D 32°, c = 5 in chloroform |
Water Solubility | Slightly soluble in water. |
BRN | 83811 |
CAS DataBase Reference | 94594-90-8(CAS DataBase Reference) |
NIST Chemistry Reference | (-)-10,2-Camphorsultam(94594-90-8) |
Safety information for (2R)-Bornane-10,2-sultam
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for (2R)-Bornane-10,2-sultam
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