Next Article in Journal
[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diyl Diacetate
Previous Article in Journal
[3S*,5S*,6S*]-1,7-Dioxaspiro[5.5]undecane-3,5-diol
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 2
Issue 6
10.3390/M21
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

[4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undec-4,5-diyl Diacetate

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), M21; https://doi.org/10.3390/M21
Submission received: 18 June 1997 / Published: 20 June 1997
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 02 m21 i001
To a solution of [4R*,5R*,6S*]-1,7-dioxaspiro[5.5]undecane-4,5-diol (1) (50 mg, 0.27 mmol) in dichloromethane (10 ml) was added triethylamine (100 mg, 0.99 mmol), acetic anhydride (67 mg, 0.66 mmol) and 4-dimethylaminopyridine (3 mg). The reaction mixture allowed to stand at room temperature for 1 h, then quenched with water (2.0 ml), extracted with dichloromethane (2x 50 ml) and dried over sodium sulphate. Removal of the solvent under reduced pressure gave a pale yellow oil, that was purified by flash chromatography using hexane-ethyl acetate (2:1) as eluent to afford [4R*,5R*,6S*]-1,7-dioxaspiro[5.5]undec-4,5-diyl diacetate (2) (69 mg, 94%) as a colourless oil.
High Res. MS calc. for C13H20O6 M+H (CI, NH3) 273.1338, found: M+ 273.1337.
IR (Nujol) cm-1 1731 [s, C=O (ester)], 1080 (s, C-O).
1H-NMR (200 MHz, CDCl3) 1.39-1.82 (8H, m, 4-CH2, 9-CH2, 10-CH2, and 11-CH2), 2.07 (3H, s, Ac), 2.09 (3H, s, Ac), 3.53-3.82 (4H, m, 2-CH2, and 8-CH2 ), 3.94 (1H, ddd, J 2ax,2eq 11.3, 2ax,3ax 11.3, and 2ax,3eq 3.0 Hz, 2ax-H), 4.81-4.85 (2H, m, 4-H and 5-H).
13C-NMR (50 MHz, CDCl3) 17.6, 24.6 (CH2, C-9 and C-10), 20.8, 21.1 (CH3, 2x Ac), 26.3 (CH2, C-3), 29.3 (CH2, C-11), 55.9 (CH2, C-2), 60.8 (CH2, C-8), 67.9 (CH, C-4), 70.0 (CH, C-5), 96.1 (quat, C-6), 170.1, 171.0 (quat, 2x C=O).
CI-MS 273 (M+H, 20%), 213 (100), 153 (30), 101 (5).

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.

Share and Cite

MDPI and ACS Style

Brimble, M.A.; Johnston, A.D. [4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undec-4,5-diyl Diacetate. Molecules 1997, 2, M21. https://doi.org/10.3390/M21

AMA Style

Brimble MA, Johnston AD. [4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undec-4,5-diyl Diacetate. Molecules. 1997; 2(6):M21. https://doi.org/10.3390/M21

Chicago/Turabian Style

Brimble, Margaret A., and Andrew D. Johnston. 1997. "[4R*,5R*,6S*]-1,7-Dioxaspiro[5.5]undec-4,5-diyl Diacetate" Molecules 2, no. 6: M21. https://doi.org/10.3390/M21

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