1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its condensed structural formula is [–(CH
2)3–O–O–].[1][2]
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| Names | |
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| Preferred IUPAC name
1,2-Dioxolane | |
| Systematic IUPAC name
1,2-Dioxacyclopentane | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C3H6O2 | |
| Molar mass | 74.079 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The compound is an organic peroxide, specifically an endoperoxide, and a structural isomer of the much more common 1,3-dioxolane, which is often called simply "dioxolane".
Synthesis
editSynthesis methods for the 1,2-dioxolane core structure include oxidation of cyclopropane derivatives with singlet oxygen[3] or molecular oxygen with a suitable catalyst,[4][5] the use of autooxidation, nucleophilic displacement with hydrogen peroxide, treatment with mercury(II) nitrate, photolysis of extended π-systems,[6] reaction of a bis-silylperoxide and an alkene,[7] or reaction with a 2-perhydroxy 4-alkene with diethylamine[8] or mercury(II) acetate.[9][10]
Occurrence
editSome derivatives occur naturally, for example in Calophyllum dispar and from the seeds of the mamey (Mammea americana).[6] Plakinic acid A (3,5-peroxy 3Z,5Z,7,11-tetramethyl 13-phenyl-8E,12E-tridecadienoic acid) and similar compounds were isolated from sponges of the Plakortis genus.[11][12] Nardosinone is a sesquiterpene derivative with a 1,2-dioxolane element isolated from the plant Adenosma caeruleum.[13]
Uses
editSynthetic and natural dioxolane derivatives have been used or considered as antimalarial drugs.[6][7] Plakinic acid A and related compounds showed antifungal action.[11]
See also
editReferences
edit- ^ Lay TH, Bozzelli JW (199). "Enthalpies of formation of cyclic alkyl peroxides: Dioxirane, 1,2-dioxetane, 1,2-dioxolane, and 1,2-dioxane". Chemical Physics Letters. 268 (1–2): 175–179. Bibcode:1997CPL...268..175L. doi:10.1016/S0009-2614(97)00168-1.1–2&rft.pages=175-179&rft.date=199&rft_id=info:doi/10.1016/S0009-2614(97)00168-1&rft_id=info:bibcode/1997CPL...268..175L&rft.aulast=Lay&rft.aufirst=TH&rft.au=Bozzelli, JW&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Demaison J (1982). "2.5.2.5 Elements with two or three internal rotors". Diamagnetic Molecules. Landolt-Börnstein - Group II Molecules and Radicals. Vol. 14a. pp. 415–425. doi:10.1007/10201404_40. ISBN 3-540-11365-7.415-425&rft.date=1982&rft_id=info:doi/10.1007/10201404_40&rft.isbn=3-540-11365-7&rft.aulast=Demaison&rft.aufirst=J&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Akasaka T, Fukuoka K, Ando W (1991). "Formation of 1,2-dioxolane in the singlet oxygenation of cyclopropane". Tetrahedron Letters. 32 (52): 7695–7698. doi:10.1016/0040-4039(91)80568-Q.7695-7698&rft.date=1991&rft_id=info:doi/10.1016/0040-4039(91)80568-Q&rft.aulast=Akasaka&rft.aufirst=T&rft.au=Fukuoka, K&rft.au=Ando, W&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Feldman KS, Simpson RE (1989). "Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol". Tetrahedron Letters. 30 (50): 6985–6988. doi:10.1016/S0040-4039(01)93404-5.6985-6988&rft.date=1989&rft_id=info:doi/10.1016/S0040-4039(01)93404-5&rft.aulast=Feldman&rft.aufirst=KS&rft.au=Simpson, RE&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Mata S, González J, Vicente R, López LA (2016). "Zinc-Catalyzed Multicomponent Reactions: Easy Access to Furyl-Substituted Cyclopropane and 1,2-Dioxolane Derivatives" (PDF). European Journal of Organic Chemistry. 2016 (15): 2681–2687. doi:10.1002/ejoc.201600393.2681-2687&rft.date=2016&rft_id=info:doi/10.1002/ejoc.201600393&rft.aulast=Mata&rft.aufirst=S&rft.au=González, J&rft.au=Vicente, R&rft.au=López, LA&rft_id=https://ria.asturias.es/RIA/bitstream/123456789/8188/1/Archivo.pdf&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ a b c Helesbeux JJ, Peyronnet D, Labaïed M, Grellier P, Frappier F, Seraphin D, et al. (December 2002). "Synthesis and antimalarial activity of some new 1,2-dioxolane derivatives". Journal of Enzyme Inhibition and Medicinal Chemistry. 17 (6): 431–7. doi:10.1080/1475636021000005677. PMID 12683680. S2CID 41059563.431-7&rft.date=2002-12&rft_id=https://api.semanticscholar.org/CorpusID:41059563#id-name=S2CID&rft_id=info:pmid/12683680&rft_id=info:doi/10.1080/1475636021000005677&rft.aulast=Helesbeux&rft.aufirst=JJ&rft.au=Peyronnet, D&rft.au=Labaïed, M&rft.au=Grellier, P&rft.au=Frappier, F&rft.au=Seraphin, D&rft.au=Richomme, P&rft.au=Duval, O&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ a b Martyn DC, Ramirez AP, Beattie MJ, Cortese JF, Patel V, Rush MA, et al. (December 2008). "Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum". Bioorganic & Medicinal Chemistry Letters. 18 (24): 6521–4. doi:10.1016/j.bmcl.2008.10.083. PMID 18993067.6521-4&rft.date=2008-12&rft_id=info:doi/10.1016/j.bmcl.2008.10.083&rft_id=info:pmid/18993067&rft.aulast=Martyn&rft.aufirst=DC&rft.au=Ramirez, AP&rft.au=Beattie, MJ&rft.au=Cortese, JF&rft.au=Patel, V&rft.au=Rush, MA&rft.au=Woerpel, KA&rft.au=Clardy, J&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Liu HH, Jin HX, Wu YK (2010). "Synthesis and cleavage studies of a 1,2-dioxolane-type peroxide". Chinese Journal of Chemistry. 22 (9): 1029–1033. doi:10.1002/cjoc.20040220930.1029-1033&rft.date=2010&rft_id=info:doi/10.1002/cjoc.20040220930&rft.aulast=Liu&rft.aufirst=HH&rft.au=Jin, HX&rft.au=Wu, YK&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Booldworth AJ, Tallant NA (1992). "1,2,4-Trioxane versus 1,2-dioxolane formation in the mercury(II) acetate-mediated cyclisation of hemiperoxyacetals derived from allylic hydroperoxides". Journal of the Chemical Society, Chemical Communications (5): 428. doi:10.1039/C39920000428.
- ^ Bloodworth AJ, Bothwell BD, Collins AN, Maidwell NL (1996). "A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group". Tetrahedron Letters. 37 (11): 1885–1888. doi:10.1016/0040-4039(96)00143-8.1885-1888&rft.date=1996&rft_id=info:doi/10.1016/0040-4039(96)00143-8&rft.aulast=Bloodworth&rft.aufirst=AJ&rft.au=Bothwell, BD&rft.au=Collins, AN&rft.au=Maidwell, NL&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ a b Phillipson DW, Rinehart Jr K (1983). "Antifungal peroxide-containing acids from two Caribbean sponges". Journal of the American Chemical Society. 105 (26): 7735–7736. doi:10.1021/ja00364a045.7735-7736&rft.date=1983&rft_id=info:doi/10.1021/ja00364a045&rft.aulast=Phillipson&rft.aufirst=DW&rft.au=Rinehart Jr, K&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Dai P, Trullinger TK, Liu X, Dussault PH (March 2006). "Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: synthesis and configurational assignment of plakinic acid A". The Journal of Organic Chemistry. 71 (6): 2283–92. doi:10.1021/jo0522254. PMID 16526775.2283-92&rft.date=2006-03&rft_id=info:doi/10.1021/jo0522254&rft_id=info:pmid/16526775&rft.aulast=Dai&rft.aufirst=P&rft.au=Trullinger, TK&rft.au=Liu, X&rft.au=Dussault, PH&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">
- ^ Kandur WV, Richert KJ, Rieder CJ, Thomas AM, Hu C, Ziller JW, Woerpel KA (May 2014). "Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones". Organic Letters. 16 (10): 2650–3. doi:10.1021/ol500835f. PMID 24779430.2650-3&rft.date=2014-05&rft_id=info:doi/10.1021/ol500835f&rft_id=info:pmid/24779430&rft.aulast=Kandur&rft.aufirst=WV&rft.au=Richert, KJ&rft.au=Rieder, CJ&rft.au=Thomas, AM&rft.au=Hu, C&rft.au=Ziller, JW&rft.au=Woerpel, KA&rfr_id=info:sid/en.wikipedia.org:1,2-Dioxolane" class="Z3988">