All Photos(1)

534978

Sigma-Aldrich

(R)-(−)-(2-Butenoyl)-2,10-camphorsultam

97%

Synonym(s):
(N-Crotonyl)-(2R)-bornane-10,2-sultam, (2E)-1-[(3aS,6R,7aR)-Tetrahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-2-buten-1-one
Empirical Formula (Hill Notation):
C14H21NSO3
CAS Number:
Molecular Weight:
283.39
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

optical activity

[α]24/D −100°, c = 1 in ethanol

mp

180-184 °C (lit.)

SMILES string

C\C=C\C(=O)N1[C@@H]2C[C@H]3CC[C@]2(CS1(=O)=O)C3(C)C

InChI

1S/C14H21NO3S/c1-4-5-12(16)15-11-8-10-6-7-14(11,13(10,2)3)9-19(15,17)18/h4-5,10-11H,6-9H2,1-3H3/b5-4+/t10-,11-,14-/m1/s1

InChI key

BKPQKSSKLBTRJO-MNKRUUAMSA-N

Application

(R)-(-)-(2-Butenoyl)-2,10-camphorsultam can be used:
  • In the asymmetric total synthesis of lycopodine via diastereoselective cyclization and intramolecular Mannich cyclization.
  • To prepare (S)-4,4-dichloro-3-methylbutanoic acid, which is utilized as a key intermediate for the total synthesis of dysideaproline E.

Packaging

500 mg in amber glass bottle

Certificate of Analysis

Certificate of Origin

Synthesis of dysideaproline E using organocatalysis
Owusu-Ansah E, et al.
Organic & Biomolecular Chemistry, 9(1), 265-272 (2011)
Enantioselective total synthesis of lycopodine
Yang H, et al.
Journal of the American Chemical Society, 130(29), 9238-9239 (2008)

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