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(1S,4R,5R,8R,9S,12R,13S) 12-(1S-Hydroxyethyl)-13-(3-hydroxypropyl)-5-(1,5-dimethylhexyl)-1,9-epoxy-4,8,13 Trimethyl Tricyclo [7,4,0,04,8] Tridecane

1
Laboratoire de Chimie des Substances Naturelles et des Hétérocycles, Université Cadi Ayyad, Faculté des Sciences SemLalia, BP 2390. Bd Prince My Abdellah, Marrakech. Maroc
2
LBS-UMR 6517, Centre Scientifique Saint-Jérôme, 13397 Marseille, CEDEX 20, France
*
Author to whom correspondence should be addressed.
Molecules 2001, 6(6), M221; https://doi.org/10.3390/M221
Submission received: 19 February 2001 / Accepted: 15 May 2001 / Published: 25 May 2001
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 06 m221 i001
A mixture of 1 (1 g, 2.25 mmol) and lithium aluminium hydride (0.34 g, 8.94 mmol) in 40 mL of THF was refluxed for 12 h. After being diluted with 20 mL of THF, the mixture was cooled to 0°C and carefully treated with 2 mL of distilled water. The resulting mixture was stirred for 40 min at room temperature and treated with anhydrous sodium sulfate. Filtration, and concentration under reduced pressure gave the crude product, which was purified by column chromatography on silica gel using hexane/EtOAc : 35/65) to give 2 (0.93 g, 92 %). The structure of the compound 2 was established by X-ray crystal structure determination.
Mp: 140-141 °C.
EI-MS (70eV) : 448.72 (M+.).
1H NMR (400 MHz, CDCl3) : 3.92 (t, C16-H2); 3.60 (m, C17-H); 0.74 (s, C28- H3); 1.02 (s, C29-H3); 1.09 (d, J= 6Hz, C20-H3); 0.86 (s, C19-H3); 1.25 (d, J=6Hz, C18-H3).
13C NMR (100 MHz, CDCl3): 64.74 (C1); 39.91 (C2); 32.02 (C3); 36.06 (C4); 43.15 (C5); 29.98 (C6); 30.10 (C7); 43.51 (C8); 69.34 (C9); 39.55 (C10); 28.12 (C11); 48.05 (C12); 48.69 (C13); 32.83 (C14); 38.33 (C15); 63.02 (C16); 67.26 (C17); 27.72(C18); 22.97 (C19); 18.0 (C20); 35.99 (C21); 23.78 (C22); 23.47 (C23); 22.26 (C24); 35.06 (C25); 16.21 (C26); 16.22 (C27); 15.1 (C28); 18.77 (C29).

Supplementary Materials

References

  1. Daoubi, M.; Benharref, A.; Kossareva, E.; Pierrot, M. Molecules 2000, 5, M188. [CrossRef]
  2. Guan, H. P.; Ksebati, M. B.; Kern, E. R.; ZemLicka, J. J. Org. Chem. 2000, 65, 5177–5184. [CrossRef]
Sample Availability: Available from the authors and from MDPI.

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MDPI and ACS Style

Daoubi, M.; Benharref, A.; Pierrot, M. (1S,4R,5R,8R,9S,12R,13S) 12-(1S-Hydroxyethyl)-13-(3-hydroxypropyl)-5-(1,5-dimethylhexyl)-1,9-epoxy-4,8,13 Trimethyl Tricyclo [7,4,0,04,8] Tridecane. Molecules 2001, 6, M221. https://doi.org/10.3390/M221

AMA Style

Daoubi M, Benharref A, Pierrot M. (1S,4R,5R,8R,9S,12R,13S) 12-(1S-Hydroxyethyl)-13-(3-hydroxypropyl)-5-(1,5-dimethylhexyl)-1,9-epoxy-4,8,13 Trimethyl Tricyclo [7,4,0,04,8] Tridecane. Molecules. 2001; 6(6):M221. https://doi.org/10.3390/M221

Chicago/Turabian Style

Daoubi, M., A. Benharref, and M. Pierrot. 2001. "(1S,4R,5R,8R,9S,12R,13S) 12-(1S-Hydroxyethyl)-13-(3-hydroxypropyl)-5-(1,5-dimethylhexyl)-1,9-epoxy-4,8,13 Trimethyl Tricyclo [7,4,0,04,8] Tridecane" Molecules 6, no. 6: M221. https://doi.org/10.3390/M221

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