1,2-Dithiolane

443707568 1,2-dithiolane-2D-skeletal.png 75px Dithiolane13d.png 100px Dithiolane23d.png 100px 1,2-Dithiolane (top row) and 1,3-dithiolane (bottom row) 1,2-Dithiolane correct CAS 557-22-2 102454 38226 correct EBI correct chemspider 71377 1029938 79045 6DE8XWQ974 correct chemspider 1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 correct chemspider MUZIZEZCKKMZRT-UHFFFAOYSA-N S1SCCC1 3 6 2 Ethane-1,2-dithiol 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 (\sCH2\s 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.10.1080/01961779008048732 Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties 1990 Teuber Lene Sulfur Reports 9 4 257–333 The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to oligomerization.10.1080/03086648308080483 Preparation and X-Ray Crystal Structure of the Cyclic Dimer of 1,2-Dithiolane: 1,2,6,7-Tetrathiacyclodecane 1983 Goodrow Marvin H. Olmstead Marilyn M. Musker W. Kenneth Phosphorus and Sulfur and the Related Elements 16 3 299–302 In general, 1,3-dithiols are superior reductants relative to monothiols.10.1021/ja00173a017 Predicting the stability of cyclic disulfides by molecular modeling: Effective concentrations in thiol-disulfide interchange and the design of strongly reducing dithiols 1990 Burns John A. Whitesides George M. Journal of the American Chemical Society 112 17 6296–6303 Natural occurrence Many substituted 1,2-dithiolates are found in nature.10.1080/01961779008048732 Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties 1990 Teuber Lene Sulfur Reports 9 4 257–333 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. Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study M. L. Pelchat C. Bykowski F. F. Duke D. R. Reed Chemical Senses 2011 36 1 9–17 10.1093/chemse/bjq081 20876394 3002398 The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that act by blocking the nicotinic acetylcholine receptor.10.1146/annurev-ento-120811-153645 Neuroactive Insecticides: Targets, Selectivity, Resistance, and Secondary Effects 2013 Casida John E. Durkin Kathleen A. Annual Review of Entomology 58 99–117 23317040 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. Dithiolane-S-oxides thumb|upright=0.5|Isomers of brugierol Many 1,2-dithiolanes can be oxidized to their S-oxides, which are chiral. References External links 1,3-Dithiolane Reactions