Next Article in Journal
(Z)-2-Methyl-3-(1-phenyl-ethylamino)-but-2-enoic acid ethyl ester
Previous Article in Journal
3-Methyl-3-(6,6,6a-trimethyl-hexahydro-cyclopenta[b]furan-2-yl)-butan-2-one
 
 
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

exo-N-(5,5-Dimethyl-6-methylene-bicyclo[2.2.1]hept-2-yl)-4-methyl-benzenesulfonamide

Departamento de Química Inorgánica y Orgánica, Facultad de Ciencias Experimentales, Universidad de Jaén, 23071 Jaén, Spain
*
Author to whom correspondence should be addressed.
Molbank 2005, 2005(1), M394; https://doi.org/10.3390/M394
Submission received: 16 February 2004 / Accepted: 7 June 2004 / Published: 1 July 2005
Molbank 2005 m394 i001
p-Toluenesulfonic acid (35 mg, 0.20 mmol) was added to a stirred mixture of campholenic aldehyde (1) (725 mg, 3.81 mmol) and p-toluenesulfonamide (1.22 g, 6.96 mmol) in toluene (20 mL). Then a Dean-Stark trap device was fit and the reaction refluxed for 0.5 h. After that, the mixture was cooled to 0oC, filtered through a silica gel pad and the solvent evaporated under reduced pressure to yield a residue (1.30g) which was purified by flash chromatography on silica gel, using a 2:1 Hexane/Et2O mixture as eluent, to give the title compound 2 (517 mg, 1.69 mmol, 44%).
Melting point: 110.7–114.8 oC (White crystals, from hexane)
IR (KBr, cm-1): 3274 (N-H); 3063, 1663, 881 (C=C); 3062, 811 (Ar); 1327, 1164 (SO2); 666 (C-N).
1H NMR (300 MHz, CDCl3): δ= 0.94 (3H, s, Mea-5’); 0.98 (3H, s, Meb-5’); 1.08 (1H, dt, J=13.7 Hz, 4.2 Hz, Hb-3’); 1.32 (1H, d, J=10.6 Hz, H-7’); 1.63 (1H, br d, J=10.6 Hz, H’-7’); 1.85 (1H, br d, J=2.3 Hz, H-4’); 2.14 (1H, ddd, J=13.7 Hz, 8.1 Hz, 2.5 Hz, Ha-3’); 2.41 (1H, br s, H-1’); 2.44 (3H, s, Me-4); 3.22 (1H, td, J=7.9 Hz, 4.2 Hz, H-2’); 4.59 (1H, s, CH2-6’); 4.72 (1H, s, CH2-6’); 4.87 (1H, d, J=7.9 Hz, N-H); 7.32 (2H, d, J=8.1 Hz, H-3, H-5); 7.77 (2H, d, J=8.1 Hz, H-2, H-6).
Some signals were assigned by means of 2D NMR experiments.
13C NMR (75 MHz, CDCl3): δ= 137.76 (C-1); 127.16 (C-2); 129.67 (C-3); 143.33 (C-4); 21.50 (Me-4); 52.82 (C-1’); 55.72 (C-2’); 35.23 (C-3’); 47.34 (C-4’); 41.00 (C-5’); 161.07 (C-6’); 34.02 (C-7’); 103.19 (CH2-6’); 25.30 (Mea-5’); 29.10 (Meb-5’).
Some signals were assigned by means of 2D NMR experiments.
EI-MS (70 eV, m/z): 305 (M+, 3%); 264 (2); 240 (M+–SO2H, 10); 201 (2); 185 (3); 184 (6); 155 (Ts+, 14); 150 (M+–Ts, 23); 134 (M+–TsNH2, 25); 121 (M+–TsNH–Me, 47); 108 (69); 91 (MePh+, 100); 79 (23); 65 (38); 53 (14); 41 (27).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

We wish to thank the Ministerio de Ciencia y Tecnología for financial support (R+D Project PPQ2000-1665) and the Ministerio de Educación, Cultura y Deporte for a fellowship to J. M. Castro.

Share and Cite

MDPI and ACS Style

Badía, C.; Castro, J.M.; Linares-Palomino, P.J.; Salido, S.; Altarejos, J.; Nogueras, M.; Sánchez, A. exo-N-(5,5-Dimethyl-6-methylene-bicyclo[2.2.1]hept-2-yl)-4-methyl-benzenesulfonamide. Molbank 2005, 2005, M394. https://doi.org/10.3390/M394

AMA Style

Badía C, Castro JM, Linares-Palomino PJ, Salido S, Altarejos J, Nogueras M, Sánchez A. exo-N-(5,5-Dimethyl-6-methylene-bicyclo[2.2.1]hept-2-yl)-4-methyl-benzenesulfonamide. Molbank. 2005; 2005(1):M394. https://doi.org/10.3390/M394

Chicago/Turabian Style

Badía, Concepción, Juan M. Castro, Pablo J. Linares-Palomino, Sofía Salido, Joaquín Altarejos, Manuel Nogueras, and Adolfo Sánchez. 2005. "exo-N-(5,5-Dimethyl-6-methylene-bicyclo[2.2.1]hept-2-yl)-4-methyl-benzenesulfonamide" Molbank 2005, no. 1: M394. https://doi.org/10.3390/M394

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop