Dithiolane

Dithiolane
Names
	IUPAC name Dithiolane
	Other names 1,2-Dithiolane, 1,3-dithiolane
Identifiers
CAS Number	(1,2): 557-22-2 ; (1,3): 4829-04-3 ;
3D model (JSmol)	(1,2): Interactive image; (1,3): Interactive image;
ChEBI	CHEBI:38335 ; (1,2): CHEBI:38226; (1,3): CHEBI:38079;
ChemSpider	(1,2): 71377;
PubChem CID	(1,2): 79045; (1,3): 20970;
UNII	(1,2): 6DE8XWQ974; (1,3): 341G58G6YL;
	InChI (1,2): InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N ;
	SMILES (1,2): S1SCCC1; (1,3): C1CSCS1;
Properties
Chemical formula	C3H6S2
Molar mass	106.20 g·mol−1
Related compounds
Related compounds	Ethane-1,2-dithiol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

A dithiolane is a sulfur heterocycle derived from cyclopentane by replacing two methylene bridges (-CH₂- units) with thioether groups. The parent compounds are 1,2-dithiolane and 1,3-dithiolane.

1,2-Dithiolanes are cyclic disulfides. Some dithiolanes are natural products^[1] that can be found in foods, such as asparagusic acid in asparagus.^[2] The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides which act by blocking the nicotinic acetylcholine receptor.^[3] Lipoic acid is essential for aerobic metabolism in mammals and also has strong affinity with many metals including gold, molybdenum, and tungsten.^[4] Other 1,2-dithiolanes have relevance in nanomaterials such as gold nanoparticles or transition metal dichalcogenide monolayers (TMDs) (MoS₂ and WS₂).^[5]^[6]^[7]

asparagusic acid
nereistoxin, from which insecticides including cartap and bensultap were derived
lipoic acid

1,3-Dithiolanes are important as protecting groups for carbonyl compounds, since they are inert to a wide range of conditions. Reacting a carbonyl group with 1,2-ethanedithiol converts it to a 1,3-dithiolane, as detailed below.

Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol

References

↑ Teuber, Lene (1990). "Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties". Sulfur Reports 9 (4): 257–333. doi:10.1080/01961779008048732.
↑ Pelchat, M. L.; Bykowski, C.; Duke, F. F.; Reed, D. R. (2011). "Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study". Chemical Senses 36 (1): 9–17. doi:10.1093/chemse/bjq081. PMID 20876394.
↑ Casida, John E.; Durkin, Kathleen A. (2013). "Neuroactive Insecticides: Targets, Selectivity, Resistance, and Secondary Effects". Annual Review of Entomology 58: 99–117. doi:10.1146/annurev-ento-120811-153645. PMID 23317040.
↑ "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. https://lpi.oregonstate.edu/mic/dietary-factors/lipoic-acid. Retrieved 27 August 2020.
↑ Bilewicz, Renata; Więckowska, Agnieszka; Kruszewski, Marcin; Stępkowski, Tomasz; Męczynska-Wielgosz, Sylwia; Cichowicz, Grzegorz; Piątek, Piotr; Załubiniak, Dominika et al. (2018-04-18). "Towards potent but less toxic nanopharmaceuticals – lipoic acid bioconjugates of ultrasmall gold nanoparticles with an anticancer drug and addressing unit" (in en). RSC Advances 8 (27): 14947–14957. doi:10.1039/C8RA01107A. ISSN 2046-2069. PMID 35541347.
↑ Vallan, Lorenzo; Canton-Vitoria, Ruben; Gobeze, Habtom B.; Jang, Youngwoo; Arenal, Raul; Benito, Ana M.; Maser, Wolfgang K.; D’Souza, Francis et al. (2018-10-17). "Interfacing Transition Metal Dichalcogenides with Carbon Nanodots for Managing Photoinduced Energy and Charge-Transfer Processes". Journal of the American Chemical Society 140 (41): 13488–13496. doi:10.1021/jacs.8b09204. ISSN 0002-7863. PMID 30222336. http://zaguan.unizar.es/record/87809.
↑ Tagmatarchis, Nikos; Ewels, Christopher P.; Bittencourt, Carla; Arenal, Raul; Pelaez-Fernandez, Mario; Sayed-Ahmad-Baraza, Yuman; Canton-Vitoria, Ruben (2017-06-05). "Functionalization of MoS 2 with 1,2-dithiolanes: toward donor-acceptor nanohybrids for energy conversion" (in en). npj 2D Materials and Applications 1 (1): 13. doi:10.1038/s41699-017-0012-8. ISSN 2397-7132.

External links

1,3-Dithiolane Reactions

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[1] Teuber, Lene (1990). "Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties". Sulfur Reports 9 (4): 257–333. doi:10.1080/01961779008048732.

[2] Pelchat, M. L.; Bykowski, C.; Duke, F. F.; Reed, D. R. (2011). "Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study". Chemical Senses 36 (1): 9–17. doi:10.1093/chemse/bjq081. PMID 20876394.

[3] Casida, John E.; Durkin, Kathleen A. (2013). "Neuroactive Insecticides: Targets, Selectivity, Resistance, and Secondary Effects". Annual Review of Entomology 58: 99–117. doi:10.1146/annurev-ento-120811-153645. PMID 23317040.

[4] "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. https://lpi.oregonstate.edu/mic/dietary-factors/lipoic-acid. Retrieved 27 August 2020.

[5] Bilewicz, Renata; Więckowska, Agnieszka; Kruszewski, Marcin; Stępkowski, Tomasz; Męczynska-Wielgosz, Sylwia; Cichowicz, Grzegorz; Piątek, Piotr; Załubiniak, Dominika et al. (2018-04-18). "Towards potent but less toxic nanopharmaceuticals – lipoic acid bioconjugates of ultrasmall gold nanoparticles with an anticancer drug and addressing unit" (in en). RSC Advances 8 (27): 14947–14957. doi:10.1039/C8RA01107A. ISSN 2046-2069. PMID 35541347.

[6] Vallan, Lorenzo; Canton-Vitoria, Ruben; Gobeze, Habtom B.; Jang, Youngwoo; Arenal, Raul; Benito, Ana M.; Maser, Wolfgang K.; D’Souza, Francis et al. (2018-10-17). "Interfacing Transition Metal Dichalcogenides with Carbon Nanodots for Managing Photoinduced Energy and Charge-Transfer Processes". Journal of the American Chemical Society 140 (41): 13488–13496. doi:10.1021/jacs.8b09204. ISSN 0002-7863. PMID 30222336. http://zaguan.unizar.es/record/87809.

[7] Tagmatarchis, Nikos; Ewels, Christopher P.; Bittencourt, Carla; Arenal, Raul; Pelaez-Fernandez, Mario; Sayed-Ahmad-Baraza, Yuman; Canton-Vitoria, Ruben (2017-06-05). "Functionalization of MoS 2 with 1,2-dithiolanes: toward donor-acceptor nanohybrids for energy conversion" (in en). npj 2D Materials and Applications 1 (1): 13. doi:10.1038/s41699-017-0012-8. ISSN 2397-7132.

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Dithiolane

Topic: Chemistry

References

External links