The Novel <i>Cis</i>- and <i>Trans</i>- Isomerism of α-Monosubstituted Cyclododecanone Derivatives

Mingyan Yang; Daoquan Wang; Mingan Wang

doi:doi:10.11648/j.sjc.20210906.13

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The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives

Mingyan Yang, Daoquan Wang, Mingan Wang

Published in Science Journal of Chemistry (Volume 9, Issue 6)

Received: 30 October 2021 Accepted: 23 November 2021 Published: 29 November 2021

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Abstract

The [3333]-2-one conformation is the preferred conformation of cyclododecanone and carbonyl is vertical to the near ring plane. To explore the stereochemistry of substituted cyclododecanone is beneficial to understanding their stability, reactivity and structure-activity relationships of these compounds. The cis- and trans- isomerism of the macrocyclic ketones based on the carbonyl orientation was not reported up to now. In order to confirm this isomerism, the novel cis- and trans- isomerism were theoretically observed based on the carbonyl orientation analysis in the [3333]-2-one conformation of cyclododecanone, and the cis- and trans- isomers of the -monosubstituted cyclododecanones were practically synthesized, their structures were characterized by ¹H, ¹³C NMR, HR-MS spectral data and X-ray diffraction analysis. This kind of cis- and trans- isomerism was first postulated and confirmed in the macrocyclic ketones using the -monosubstituted cyclododecanone derivatives as the representatives.

Published in	Science Journal of Chemistry (Volume 9, Issue 6)
DOI	10.11648/j.sjc.20210906.13
Page(s)	145-154
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

cis- and trans- Isomerism, -Monosubstituted Cyclododecanone, Synthesis, X-ray Diffraction

References

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Mingyan Yang, Daoquan Wang, Mingan Wang. (2021). The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives. Science Journal of Chemistry, 9(6), 145-154. https://doi.org/10.11648/j.sjc.20210906.13

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ACS Style

Mingyan Yang; Daoquan Wang; Mingan Wang. The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives. Sci. J. Chem. 2021, 9(6), 145-154. doi: 10.11648/j.sjc.20210906.13

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Mingyan Yang, Daoquan Wang, Mingan Wang. The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives. Sci J Chem. 2021;9(6):145-154. doi: 10.11648/j.sjc.20210906.13

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@article{10.11648/j.sjc.20210906.13,
  author = {Mingyan Yang and Daoquan Wang and Mingan Wang},
  title = {The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives},
  journal = {Science Journal of Chemistry},
  volume = {9},
  number = {6},
  pages = {145-154},
  doi = {10.11648/j.sjc.20210906.13},
  url = {https://doi.org/10.11648/j.sjc.20210906.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20210906.13},
  abstract = {The [3333]-2-one conformation is the preferred conformation of cyclododecanone and carbonyl is vertical to the near ring plane. To explore the stereochemistry of substituted cyclododecanone is beneficial to understanding their stability, reactivity and structure-activity relationships of these compounds. The cis- and trans- isomerism of the macrocyclic ketones based on the carbonyl orientation was not reported up to now. In order to confirm this isomerism, the novel cis- and trans- isomerism were theoretically observed based on the carbonyl orientation analysis in the [3333]-2-one conformation of cyclododecanone, and the cis- and trans- isomers of the -monosubstituted cyclododecanones were practically synthesized, their structures were characterized by 1H, 13C NMR, HR-MS spectral data and X-ray diffraction analysis. This kind of cis- and trans- isomerism was first postulated and confirmed in the macrocyclic ketones using the -monosubstituted cyclododecanone derivatives as the representatives.},
 year = {2021}
}

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TY  - JOUR
T1  - The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives
AU  - Mingyan Yang
AU  - Daoquan Wang
AU  - Mingan Wang
Y1  - 2021/11/29
PY  - 2021
N1  - https://doi.org/10.11648/j.sjc.20210906.13
DO  - 10.11648/j.sjc.20210906.13
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 145
EP  - 154
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20210906.13
AB  - The [3333]-2-one conformation is the preferred conformation of cyclododecanone and carbonyl is vertical to the near ring plane. To explore the stereochemistry of substituted cyclododecanone is beneficial to understanding their stability, reactivity and structure-activity relationships of these compounds. The cis- and trans- isomerism of the macrocyclic ketones based on the carbonyl orientation was not reported up to now. In order to confirm this isomerism, the novel cis- and trans- isomerism were theoretically observed based on the carbonyl orientation analysis in the [3333]-2-one conformation of cyclododecanone, and the cis- and trans- isomers of the -monosubstituted cyclododecanones were practically synthesized, their structures were characterized by 1H, 13C NMR, HR-MS spectral data and X-ray diffraction analysis. This kind of cis- and trans- isomerism was first postulated and confirmed in the macrocyclic ketones using the -monosubstituted cyclododecanone derivatives as the representatives.
VL  - 9
IS  - 6
ER  -

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Author Information

Mingyan Yang

Department of Applied Chemistry, College of Sciences, China Agricultural University, Beijing, P. R. China
Daoquan Wang

Department of Applied Chemistry, College of Sciences, China Agricultural University, Beijing, P. R. China
Mingan Wang

Department of Applied Chemistry, College of Sciences, China Agricultural University, Beijing, P. R. China

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APA Style

Mingyan Yang, Daoquan Wang, Mingan Wang. (2021). The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives. Science Journal of Chemistry, 9(6), 145-154. https://doi.org/10.11648/j.sjc.20210906.13

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ACS Style

Mingyan Yang; Daoquan Wang; Mingan Wang. The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives. Sci. J. Chem. 2021, 9(6), 145-154. doi: 10.11648/j.sjc.20210906.13

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AMA Style

Mingyan Yang, Daoquan Wang, Mingan Wang. The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives. Sci J Chem. 2021;9(6):145-154. doi: 10.11648/j.sjc.20210906.13

Copy | Download

@article{10.11648/j.sjc.20210906.13,
  author = {Mingyan Yang and Daoquan Wang and Mingan Wang},
  title = {The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives},
  journal = {Science Journal of Chemistry},
  volume = {9},
  number = {6},
  pages = {145-154},
  doi = {10.11648/j.sjc.20210906.13},
  url = {https://doi.org/10.11648/j.sjc.20210906.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20210906.13},
  abstract = {The [3333]-2-one conformation is the preferred conformation of cyclododecanone and carbonyl is vertical to the near ring plane. To explore the stereochemistry of substituted cyclododecanone is beneficial to understanding their stability, reactivity and structure-activity relationships of these compounds. The cis- and trans- isomerism of the macrocyclic ketones based on the carbonyl orientation was not reported up to now. In order to confirm this isomerism, the novel cis- and trans- isomerism were theoretically observed based on the carbonyl orientation analysis in the [3333]-2-one conformation of cyclododecanone, and the cis- and trans- isomers of the -monosubstituted cyclododecanones were practically synthesized, their structures were characterized by 1H, 13C NMR, HR-MS spectral data and X-ray diffraction analysis. This kind of cis- and trans- isomerism was first postulated and confirmed in the macrocyclic ketones using the -monosubstituted cyclododecanone derivatives as the representatives.},
 year = {2021}
}

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TY  - JOUR
T1  - The Novel Cis- and Trans- Isomerism of α-Monosubstituted Cyclododecanone Derivatives
AU  - Mingyan Yang
AU  - Daoquan Wang
AU  - Mingan Wang
Y1  - 2021/11/29
PY  - 2021
N1  - https://doi.org/10.11648/j.sjc.20210906.13
DO  - 10.11648/j.sjc.20210906.13
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 145
EP  - 154
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20210906.13
AB  - The [3333]-2-one conformation is the preferred conformation of cyclododecanone and carbonyl is vertical to the near ring plane. To explore the stereochemistry of substituted cyclododecanone is beneficial to understanding their stability, reactivity and structure-activity relationships of these compounds. The cis- and trans- isomerism of the macrocyclic ketones based on the carbonyl orientation was not reported up to now. In order to confirm this isomerism, the novel cis- and trans- isomerism were theoretically observed based on the carbonyl orientation analysis in the [3333]-2-one conformation of cyclododecanone, and the cis- and trans- isomers of the -monosubstituted cyclododecanones were practically synthesized, their structures were characterized by 1H, 13C NMR, HR-MS spectral data and X-ray diffraction analysis. This kind of cis- and trans- isomerism was first postulated and confirmed in the macrocyclic ketones using the -monosubstituted cyclododecanone derivatives as the representatives.
VL  - 9
IS  - 6
ER  -

Copy | Download