376612
(1S)-10-Camphorsulfonamide
96%
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About This Item
Empirical Formula (Hill Notation):
C10H17NO3S
CAS Number:
Molecular Weight:
231.31
MDL number:
UNSPSC Code:
12352115
PubChem Substance ID:
NACRES:
NA.22
Assay
96%
optical activity
[α]20/D +22°, c = 1 in methanol
mp
129-132 °C (lit.)
functional group
ketone
SMILES string
CC1(C)[C@@H]2CC[C@@]1(CS(N)(=O)=O)C(=O)C2
InChI
1S/C10H17NO3S/c1-9(2)7-3-4-10(9,8(12)5-7)6-15(11,13)14/h7H,3-6H2,1-2H3,(H2,11,13,14)/t7-,10-/m1/s1
InChI key
SBLUNABTQYDFJM-GMSGAONNSA-N
Application
(1S)-10-Camphorsulfonamide can be used:
- As a template in molecule imprinted polymer (MIP) silica-based open tubular columns.
- To prepare pyrrolidine–camphor based organocatalysts, applicable in Michael reaction of aldehydes with nitroalkenes.
- To prepare prolyl sulfonamide organocatalysts, which are employed in the asymmetric Aldol reaction.
Other Notes
Sign of optical rotation varies with solvent
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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4-Substituted prolyl sulfonamides as enantioselective organocatalysts for aldol reactions
Bellis E, et al.
Synthesis, 2005(14), 2407-2413 (2005)
Comparison of enantioselective CEC separation of OT-MIP capillary columns with templates of various camphor derivatives made by the pre-established general preparation protocol
Zaidi SA, et al.
Bull. Korean Chem. Soc., 31(10), 2935-2935 (2010)
Jiang Weng et al.
Chirality, 24(4), 271-275 (2012-01-27)
Several pyrrolidine-camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (syn:anti up to 92:8), and good
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