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Short Note

[3R*,5S*,6S*]-5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-yl 3,5-Dinitrobenzoate

by
Margaret A. Brimble
* and
Andrew D. Johnston
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
Molecules 1997, 2(6), M17; https://doi.org/10.3390/M17
Submission received: 16 June 1997 / Published: 20 June 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m17 i001
To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 ml), was added triethylamine (56 mg, 0.55 mmol), 4-dimethylaminopyridine (~1 mg), and 3,5-dinitrobenzoyl chloride (64 mg, 0.28 mmol) and the resultant solution allowed to stand at room temperature for 48 h. Removal of the solvent at reduced pressure gave a pale yellow oil, that was purified by flash chromatography using hexane-ethyl acetate (6:4) as eluent to afford the title compound (1) (46 mg, 45%) as pale yellow plates.
M.p. 54-56 deg.C.
IR (Nujol) cm-1 3680-3100 (br, s, OH), 1723 (s, C=O), 1110, 1083 (s, C-O).
High Res. MS calc. for C16H18N2O9 M+ 382.1012, found: M+, 382.0988.
1H-NMR (400 MHz, CDCl3) 1.35 (1H, ddd, J11ax,11eq 13.4, J11ax,10ax 13.4 and J11ax,10eq 4.8 Hz, 11ax-H), 1.41-1.72 (4H, m, 9-CH2 and 10-CH2), 2.01 (1H, dt, J11eq,11ax 13.4 and J11eq,10 2.8 Hz, 11eq-H), 2.09 (1H, dddd, J4eq,4ax 15.3, J4eq,5 2.5, J4eq,3 2.5 and J4eq,2eq 2.5 Hz, 4eq-H), 2.12 (1H, m, OH), 2.35 (1H, ddd, J4ax,4eq 15.3, J4ax,5 3.6 and J4ax,3 3.6 Hz, 4ax-H), 3.44 (1H, m, 5-H), 3.56-3.67 (2H, m, 8-CH2), 3.85 (1H, ddd, J2ax,2eq 13.3, J2ax,3 2.5 and J2ax,4ax 2.5 Hz, 2eq-H), 3.95 (1H, dd, J2eq,2ax 13.3 and J2eq,3 1.9 Hz, 2eq-H), 5.14 (1H, m, 3-H), 9.07-9.14 (3H, m, Ar-H).
13C-NMR (100 MHz, CDCl3) 18.0, 24.8, 29.5, 30.8 (CH2, C-4, C-9, C-10 and C-11), 61.4, 61.5 (CH2, C-2 and C-8), 68.9 (CH, C-3), 70.6 (CH, C-5), 96.5 (quat, C-6), 122.4 (CH, C-4'), 129.4 (CH, C-2' and C-6'), 133.9 (quat , C-1'), 148.6 148.7 (quat, C-3' and C-5'), 162.0 (quat, C=O).
CI-MS 382 (M+, 2%), 295 (40), 213 (30), 195 (80), 179 (20), 149 (60), 114 (38), 101 (100), 83 (33), 75 (65), 69 (90), 59 (20), 55 (80), 41 (59).

Supplementary materials

Supplementary File 1Supplementary File 2

Acknowledgment

The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.
  • Sample Availability: No sample available.

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MDPI and ACS Style

Brimble, M.A.; Johnston, A.D. [3R*,5S*,6S*]-5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-yl 3,5-Dinitrobenzoate. Molecules 1997, 2, M17. https://doi.org/10.3390/M17

AMA Style

Brimble MA, Johnston AD. [3R*,5S*,6S*]-5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-yl 3,5-Dinitrobenzoate. Molecules. 1997; 2(6):M17. https://doi.org/10.3390/M17

Chicago/Turabian Style

Brimble, Margaret A., and Andrew D. Johnston. 1997. "[3R*,5S*,6S*]-5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-yl 3,5-Dinitrobenzoate" Molecules 2, no. 6: M17. https://doi.org/10.3390/M17

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