1,2-Dithiolane

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1,2-Dithiolane
1,2-dithiolane-2D-skeletal.png
Dithiolane13d.png
Names
IUPAC name
1,2-Dithiolane
Identifiers
3D model (JSmol)
102454
ChEBI
ChemSpider
1029938
PubChem CID
UNII
  • InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 Yes check.svgY
    Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N Yes check.svgY
  • S1SCCC1
Properties
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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1,2-Dithiolane is an organosulfur compound with the formula S2(CH2)3. It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges (-CH
2- units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especially lipoic acid and its derivatives, are often essential for life. Several occur naturally. [1]

Contents

The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to oligomerization. [2] In general, 1,3-dithiols are superior reductants relative to monothiols. [3]

Natural occurrence

Many substituted 1,2-dithiolates are found in nature. [4] The most common is lipoic acid, a chiral dithiolane, which features a pentanoic acid substituent. It is essential for aerobic metabolism in mammals.

Some 1,2-dithiolane are found in some foods, such as asparagusic acid in asparagus. [5] The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that act by blocking the nicotinic acetylcholine receptor. [6]

Several alkyl-substituted 1,2-dithiolanes occur in the scent glands of skunks and related mammals. These include 3,3-dimethyl-, 3-propyl-, 3-ethyl-1,2-dithiolane, and others. [4]

Dithiolane-S-oxides

Isomers of brugierol Brugierols.svg
Isomers of brugierol

Many 1,2-dithiolanes can be oxidized to their S-oxides, which are chiral. [4]

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. ↑ Goodrow, Marvin H.; Olmstead, Marilyn M.; Musker, W. Kenneth (1983). "Preparation and X-Ray Crystal Structure of the Cyclic Dimer of 1,2-Dithiolane: 1,2,6,7-Tetrathiacyclodecane". Phosphorus and Sulfur and the Related Elements. 16 (3): 299–302. doi:10.1080/03086648308080483.
  3. ↑ Burns, John A.; Whitesides, George M. (1990). "Predicting the stability of cyclic disulfides by molecular modeling: Effective concentrations in thiol-disulfide interchange and the design of strongly reducing dithiols". Journal of the American Chemical Society. 112 (17): 6296–6303. doi:10.1021/ja00173a017.
  4. 1 2 3 4 5 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.
  5. ↑ 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. PMC   3002398 . PMID   20876394.
  6. ↑ 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.
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