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Thietane

| NFPA-H = 2 | NFPA-F = 4 | NFPA-R = 1

Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom. Some derivatives are of interest as drugs.

Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues. Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.

Synthesis

Thietanes are the subject of many preparative studies. They are traditionally produced in modest or poor yields from 1,3-difunctionalized alkanes. One example is the reaction of trimethylene carbonate and potassium thiocyanate.

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An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide.

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Reactions

Nucleophiles like butyllithium can open the ring in thietane. Thietane also reacts with bromine. :[[File:Thietan_Disulfid.png|500px]]

References

References

  1. Leśniak, S. (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III.
  2. Block, E. (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II.
  3. (2022). "Thietanes and Derivatives thereof in Medicinal Chemistry". Current Topics in Medicinal Chemistry.
  4. (2016). "Behavioral responses of CD-1 mice to six predator odor components". Chem. Senses.
  5. (2013). "Mouse alarm pheromone shares structural similarity with predator scents". Proc. Natl. Acad. Sci. U.S.A..
  6. (2016). "Smelling sulfur: Copper and silver regulate the response of human odorant receptor OR2T11 to low molecular weight thiols". Journal of the American Chemical Society.
  7. (2020). "Synthesis of Thietanes from Saturated Three-membered Heterocycles". Asian Journal of Organic Chemistry.
  8. (2020). "Recent synthesis of thietanes". Beilstein Journal of Organic Chemistry.
  9. (1966). "Thietanes". Chemical Reviews.
  10. (1958). "A New Synthesis of Small Ring Cyclic Sulfides". Journal of the American Chemical Society.
  11. (1985). "Organosulfur chemistry. II. Use of dimethyl sulfoxide; A facile synthesis of cyclic sulfides.". Chemical and Pharmaceutical Bulletin.
  12. (1954). "The Reaction of Thiacyclopropanes (Olefin Sulfides) and Thiacyclobutanes with Organolithium Compounds". Journal of the American Chemical Society.
  13. (1953). "Reactions of Trimethylene Sulfide with Chlorine and Bromine". Journal of the American Chemical Society.
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sulfur-heterocycles four-membered-rings foul-smelling-chemicals
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