Dithiolane

Dithiolane  |

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Names
IUPAC name

Dithiolane

Other names

1,2-Dithiolane, 1,3-dithiolane

Identifiers

CAS Number

* (1,2): 557-22-2 Y
* (1,3): 4829-04-3 Y

3D model (JSmol)

* (1,2): Interactive image
* (1,3): Interactive image

ChEBI |

* CHEBI:38335 Y
* (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 Y

Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N Y

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).

Y verify (what is YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

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.

## References

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.

## External links

* 1,3-Dithiolane Reactions

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*[CID]: Compound ID