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Chemical compound From Wikipedia, the free encyclopedia
Dioxolane is a heterocyclic acetal with the chemical formula (CH2)2O2CH2. It is related to tetrahydrofuran (THF) by replacement of the methylene group (CH2) at the 2-position with an oxygen atom. The corresponding saturated 6-membered C4O2 rings are called dioxanes. The isomeric 1,2-dioxolane (wherein the two oxygen centers are adjacent) is a peroxide. 1,3-dioxolane is used as a solvent and as a comonomer in polyacetals.
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Names | |||
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Preferred IUPAC name
1,3-Dioxolane[2] | |||
Systematic IUPAC name
1,3-Dioxacyclopentane | |||
Other names | |||
Identifiers | |||
3D model (JSmol) |
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.010.422 | ||
EC Number |
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PubChem CID |
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UNII | |||
UN number | 1166 | ||
CompTox Dashboard (EPA) |
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Properties | |||
C3H6O2 | |||
Molar mass | 74.08 g/mol | ||
Density | 1.06 g/cm3 | ||
Melting point | −95 °C (−139 °F; 178 K) | ||
Boiling point | 75 °C (167 °F; 348 K) | ||
Hazards | |||
GHS labelling:[4] | |||
Danger | |||
H225 | |||
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dioxolanes are a group of organic compounds containing the dioxolane ring. Dioxolanes can be prepared by acetalization of aldehydes and ketalization of ketones with ethylene glycol.[5]
(+)-cis-Dioxolane is the trivial name for L-(+)-cis-2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide which is a muscarinic acetylcholine receptor agonist.
Organic compounds containing carbonyl groups sometimes need protection so that they do not undergo reactions during transformations of other functional groups that may be present. A variety of approaches to protection and deprotection of carbonyls[6] including as dioxolanes[7] are known. For example, consider the compound methyl cyclohexanone-4-carboxylate, where lithium aluminium hydride reduction will produce 4-hydroxymethylcyclohexanol. The ester functional group can be reduced without affecting the ketone by protecting the ketone as a ketal. The ketal is produced by acid catalysed reaction with ethylene glycol, the reduction reaction carried out, and the protecting group removed by hydrolysis to produce 4-hydroxymethylcyclohexanone.
NaBArF4 can also be used for deprotection of acetal or ketal-protected carbonyl compounds.[6][7] For example, deprotection of 2-phenyl-1,3-dioxolane to benzaldehyde can be achieved in water in five minutes at 30 °C.[8]
Neosporol is a natural product that includes a 1,3-dioxolane moiety, and is an isomer of sporol which has a 1,3-dioxane ring.[9] The total synthesis of both compounds has been reported, and each includes a step in which a dioxolane system is formed using trifluoroperacetic acid (TFPAA), prepared by the hydrogen peroxide – urea method.[10][11] This method involves no water, so it gives a completely anhydrous peracid,[12] necessary in this case as the presence of water would lead to unwanted side reactions.[10]
In the case of neosporol, a Prilezhaev reaction[13] with trifluoroperacetic acid is used to convert a suitable allyl alcohol precursor to an epoxide, which then undergoes a ring-expansion reaction with a proximate carbonyl functional group to form the dioxolane ring.[10][11]
A similar approach is used in the total synthesis of sporol, with the dioxolane ring later expanded to a dioxane system.[9]
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