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Short Note

[3R*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Bis(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), M18; https://doi.org/10.3390/M18
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 m18 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 cm3), was added triethylamine (60 mg, 0.59 mmol), 4-dimethylaminopyridine (~1 mg), 3,5-dinitrobenzoyl chloride (136 mg, 0.59 mmol) and the resultant solution allowed to stand at room temperature for 120 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) (61 mg, 39%) as pale yellow plates.
M.p. 64-66 deg.C.
IR (Nujol) cm-1 1727 (s, C=O), 1100, 1083, 1016 (s, C-O).
High Res. MS calc. for C23H20N4O14 M+ (DEI), 576.09760 requires: M+ 576.09705.
1H-NMR (400 MHz, CDCl3) 1.43 (1H, ddd, J11ax,11eq 12.3, J11ax,10ax 12.3 and J11ax,10eq 4.6 Hz, 11ax-H), 1.62-1.96 (5H, m, 9-CH2, 10-CH2, and 11eq-H), 2.45 (1H, d, J4eq,4ax 16.3 Hz, 4eq-H), 2.72 (1H, ddd, J4ax,4eq 16.3, J4ax,5 4.1 and J4ax,3 4.1 Hz, 4ax-H), 3.72-3.78 (2H, m, 8-CH2), 4.06-4.17 (2H, m, 2-CH2), 5.11-5.20 (2H, m, 5-H and 3-H), 8.97-9.19 (6H, m, Ar-H).
13C-NMR (100 MHz, CDCl3) 17.8, 24.5, 27.4, 30.9 (CH2, C-4, C-9, C-10 and C-11), 61.0, 61.3 (CH2, C-8 and C-2), 68.7 (CH, C-3), 71.6 (CH, C-5), 94.8 (quat, C-6), 122.4, 122.7 (CH, Ar-C), 129.1, 129.2 (quat, C-NO2), 148.8 ( quat, C-1', C-1''), 162.0 (quat, 2 x C=O).
DEI-MS 576 (M+, 100), 548 (50), 646 (48), 521 (60), 504 (100), 476 (100), 266 (75).

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: Available from MDPI, MDPI 11864.

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MDPI and ACS Style

Brimble, M.A.; Johnston, A.D. [3R*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Bis(3,5-dinitrobenzoate). Molecules 1997, 2, M18. https://doi.org/10.3390/M18

AMA Style

Brimble MA, Johnston AD. [3R*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Bis(3,5-dinitrobenzoate). Molecules. 1997; 2(6):M18. https://doi.org/10.3390/M18

Chicago/Turabian Style

Brimble, Margaret A., and Andrew D. Johnston. 1997. "[3R*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Bis(3,5-dinitrobenzoate)" Molecules 2, no. 6: M18. https://doi.org/10.3390/M18

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