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376612

Sigma-Aldrich

(1S)-10-Camphorsulfonamide

96%

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About This Item

Empirical Formula (Hill Notation):
C10H17NO3S
CAS Number:
60933-63-3
Molecular Weight:
231.31
MDL number:
MFCD00075611
UNSPSC Code:
12352115
PubChem Substance ID:
24863455
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.[1]
  • To prepare pyrrolidine–camphor based organocatalysts, applicable in Michael reaction of aldehydes with nitroalkenes.[2]
  • To prepare prolyl sulfonamide organocatalysts, which are employed in the asymmetric Aldol reaction.[3]

Other Notes

Sign of optical rotation varies with solvent

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBF8995
10618DH
08519MD
12507CR
06921PR

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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
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)
4-Substituted prolyl sulfonamides as enantioselective organocatalysts for aldol reactions
Bellis E, et al.
Synthesis, 2005(14), 2407-2413 (2005)

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