Chemistry:Thietane
Thietane is a heterocyclic compound containing a saturated four-membered ring with three carbon atoms and one sulfur atom.[1][2] Some derivatives are of interest as drugs.[3]
Thietane, and its derivative 2-propylthietane, are strong-smelling mouse alarm pheromones and predator scent analogues.[4][5] Both the mouse and human olfactory receptors MOR244-3 and OR2T11, respectively, were found to respond to thietane in the presence of copper.[6]
Synthesis
Thietanes are the subject of many preparative studies.[7][8] They are traditionally produced in modest or poor yields from 1,3-difunctionalized alkanes.[9] One example is the reaction of trimethylene carbonate and potassium thiocyanate.[10]
- C
4H
6O
3 + KSCN → C
3H
6S + KOCN + CO
2
An improved synthesis method is the reaction of 1,3-dibromopropane and sodium sulfide.[11]
- Br–(CH
2)
3–Br + Na
2S → C
3H
6S + 2 NaBr
Reactions
Nucleophiles like butyllithium can open the ring in thietane.[12] Thietane also reacts with bromine.[13]
- 500px
References
- ↑ Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III 2 (7): 389–428. doi:10.1016/B978-008044992-0.00207-8.
- ↑ Block, E; DeWang, M (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II 1 (24): 773–802. doi:10.1016/B978-008096518-5.00024-1.
- ↑ Francisco, Karol R.; Ballatore, Carlo (2022). "Thietanes and Derivatives thereof in Medicinal Chemistry". Current Topics in Medicinal Chemistry 22 (15): 1219–1234. doi:10.2174/1568026622666220511154228. PMID 35546768.
- ↑ Sievert, Thorbjörn; Laska, Matthias (2016). "Behavioral responses of CD-1 mice to six predator odor components". Chem. Senses 41 (5): 399–406. doi:10.1093/chemse/bjw015. PMID 26892309.
- ↑ Brechbuhl, J; Moine, F; Klaey, M; Nenniger-Tosato, M; Hurni, N; Sporkert, F; Giroud, C; Broillet, MC (2013). "Mouse alarm pheromone shares structural similarity with predator scents". Proc. Natl. Acad. Sci. U.S.A. 110 (12): 4762–4767. doi:10.1073/pnas.1214249110. PMID 23487748. Bibcode: 2013PNAS..110.4762B.
- ↑ Li, Shengju; Ahmed, Lucky; Zhang, Ruina; Pan, Yi; Matsunami, Hiroaki; Burger, Jessica L; Block, Eric; Batista, Victor S et al. (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 138 (40): 13281–13288. doi:10.1021/jacs.6b06983. PMID 27659093. Bibcode: 2016JAChS.13813281L.
- ↑ Xu, Jiaxi (2020). "Synthesis of Thietanes from Saturated Three-membered Heterocycles". Asian Journal of Organic Chemistry 9 (7): 1008–1017. doi:10.1002/ajoc.202000219.
- ↑ Xu, Jiaxi (2020). "Recent synthesis of thietanes". Beilstein Journal of Organic Chemistry 16: 1357–1410. doi:10.3762/bjoc.16.116. PMID 32647542.
- ↑ Sander, Manfred (1966). "Thietanes". Chemical Reviews 66 (3): 341–353. doi:10.1021/cr60241a005.
- ↑ Searles, Scott; Lutz, Eugene F. (1958). "A New Synthesis of Small Ring Cyclic Sulfides". Journal of the American Chemical Society 80 (12): 3168. doi:10.1021/ja01545a071. ISSN 0002-7863. Bibcode: 1958JAChS..80.3168S.
- ↑ Nagasawa, Kazuo; Yoneta, Akemi (1985). "Organosulfur chemistry. II. Use of dimethyl sulfoxide; A facile synthesis of cyclic sulfides.". Chemical and Pharmaceutical Bulletin 33 (11): 5048–5052. doi:10.1248/cpb.33.5048. ISSN 0009-2363.
- ↑ Bordwell, F. G.; Andersen, Harry M.; Pitt, Burnett M. (1954). "The Reaction of Thiacyclopropanes (Olefin Sulfides) and Thiacyclobutanes with Organolithium Compounds". Journal of the American Chemical Society 76 (4): 1082–1085. doi:10.1021/ja01633a045. ISSN 0002-7863. Bibcode: 1954JAChS..76.1082B.
- ↑ Stewart, John M.; Burnside, Charles H. (1953). "Reactions of Trimethylene Sulfide with Chlorine and Bromine". Journal of the American Chemical Society 75 (1): 243–244. doi:10.1021/ja01097a517. ISSN 0002-7863. Bibcode: 1953JAChS..75..243S.
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