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1,2-Dithiolane

From Wikipedia, the free encyclopedia
1,2-Dithiolane
Names
IUPAC name
1,2-Dithiolane
Identifiers
3D model (JSmol)
102454
ChEBI
ChemSpider
1029938
UNII
  • InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 checkY
    Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N checkY
  • S1SCCC1
Properties
C3H6S2
Molar mass106.20 g·mol−1
Related compounds
Related compounds
Ethane-1,2-dithiol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

1,2-Dithiolane is anorganosulfur compound with the formulaS2(CH2)3. It is also classified as aheterocycle derived fromcyclopentane by replacing twomethylene bridges (-CH
2- units) with adisulfide group.1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especiallylipoic acid and its derivatives, are often essential for life. Several occur naturally.[1]

The parent 1,2-dithiolane is the disulfide derived from1,3-propanedithiol. It is however unstable with respect tooligomerization.[2] In general, 1,3-dithiols are superior reductants relative to monothiols.[3]

Natural occurrence

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

Some 1,2-dithiolane are found in some foods, such asasparagusic acid in asparagus.[5] The 4-dimethylamino derivativenereistoxin was the inspiration forinsecticides that act by blocking thenicotinic 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

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Isomers of brugierol

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

References

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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. ^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. ^abcdeTeuber, 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.

External links

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