This article is about 1,3-dioxolane. For the other dioxolane isomer, see
1,2-dioxolane .
Dioxolane[ 1] Names Preferred IUPAC name Systematic IUPAC name Other namesDioxolane
5-Crown-2
Formal glycol
[ 2] Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.010.422 EC Number UNII UN number 1166 InChI=1S/C3H6O2/c1-2-4-5-3-1/h1-3H2
Y Key: SNQXJPARXFUULZ-UHFFFAOYSA-N
Y InChI=1/C3H6O2/c1-2-4-5-3-1/h1-3H2
Key: SNQXJPARXFUULZ-UHFFFAOYAS
Properties C3 H6 O2 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).
Chemical compound
Dioxolane is aheterocyclic acetal with thechemical formula (CH2 )2 O2 CH2 . It is related totetrahydrofuran (THF) by replacement of themethylene group (CH2 ) at the 2-position with an oxygen atom. The corresponding saturated 6-membered C4 O2 rings are calleddioxanes . Theisomeric 1,2-dioxolane (wherein the two oxygen centers are adjacent) is aperoxide . 1,3-dioxolane is used as asolvent and as a comonomer inpolyacetals .
As a class of compounds [ edit ] Dioxolanes are a group oforganic compounds containing the dioxolane ring. Dioxolanes can be prepared byacetalization ofaldehydes andketalization ofketones withethylene glycol .[ 5]
synthesis of dioxolane group (+)-cis -Dioxolane is thetrivial name forL -(+)-cis -2-methyl-4-trimethylammoniummethyl-1,3-dioxolane iodide which is amuscarinic acetylcholine receptor agonist .
Organic compounds containingcarbonyl groups sometimes needprotection so that they do not undergo reactions during transformations of otherfunctional groups that may be present. A variety of approaches to protection and deprotection of carbonyls[ 6] [ 7] lithium aluminium hydride reduction will produce 4-hydroxymethylcyclohexanol. The ester functional group can be reduced without affecting theketone by protecting the ketone as aketal . The ketal is produced by acid catalysed reaction withethylene 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] benzaldehyde can be achieved in water in five minutes at 30 °C.[ 8]
PhCH(OCH2 )2 + H2 O → 30 °C / 5 min NaBAr 4 {\displaystyle {\ce {->[{\ce {NaBAr4}}][{\text{30 °C / 5 min}}]}}} HOCH2 CH2 OH Neosporol is anatural product that includes a 1,3-dioxolanemoiety , and is an isomer ofsporol which has a 1,3-dioxane ring.[ 9] total synthesis of both compounds has been reported, and each includes a step in which a dioxolane system is formed usingtrifluoroperacetic acid (TFPAA), prepared by thehydrogen peroxide – urea method.[ 10] [ 11] anhydrous peracid,[ 12] side reactions .[ 10]
CF3 3 H2 2 2 2 CF3 CF3 CO(NH2 2 In the case of neosporol, aPrilezhaev reaction [ 13] allyl alcohol precursor to anepoxide , which then undergoes a ring-expansion reaction with a proximatecarbonyl 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]
^ 1,3-Dioxolane atSigma-Aldrich ^ formal glycol - PubChem Public Chemical Database ^ "Front Matter".Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) . Cambridge:The Royal Society of Chemistry . 2014. p. 145.doi :10.1039/9781849733069-FP001 .ISBN 978-0-85404-182-4 ^ "1,3-Dioxolane" .pubchem.ncbi.nlm.nih.gov .^ R. A. Daignault, E. L. Eliel (1973)."2-Cyclohexyloxyethanol (involves acetalisation of cyclohexanone)" .Organic Syntheses Collected Volumes , vol. 5, p. 303^a b Greene, Theodora W.; Wuts, Peter G. M. (1999). "Dimethyl acetals".Greene's Protective Groups in Organic Synthesis Wiley-Interscience . pp. 297– 304,724– 727.ISBN 9780471160199 Archived from the original on December 3, 2016. RetrievedJune 20, 2017 . ^a b Greene, Theodora W.; Wuts, Peter G. M. (1999). "1,3-Dioxanes, 1,3-Dioxolanes".Greene's Protective Groups in Organic Synthesis Wiley-Interscience . pp. 308– 322,724– 727.ISBN 9780471160199 Archived from the original on December 7, 2016. RetrievedJune 20, 2017 . ^ Chang, Chih-Ching; Liao, Bei-Sih; Liu, Shiuh-Tzung (2007). "Deprotection of Acetals and Ketals in a Colloidal Suspension Generated by Sodium Tetrakis(3,5-trifluoromethylphenyl)borate in Water".Synlett 2007 (2):283– 287.doi :10.1055/s-2007-968009 . ^a b Pirrung, Michael C.; Morehead, Andrew T.; Young, Bruce G., eds. (2000)."10. Neosporol, Sporol" .Part B: Bicyclic and Tricyclic Sesquiterpenes . The Total Synthesis of Natural Products. Vol. 11.John Wiley & Sons . pp. 222– 224.ISBN 9780470129630 ^a b c Ziegler, Fredrick E.; Metcalf, Chester A.; Nangia, Ashwini; Schulte, Gayle (1993). "Structure and total synthesis of sporol and neosporol".J. Am. Chem. Soc. 115 (7):2581– 2589.doi :10.1021/ja00060a006 . ^a b Caster, Kenneth C.; Rao, A. Somasekar; Mohan, H. Rama; McGrath, Nicholas A.; Brichacek, Matthew (2012). "Trifluoroperacetic Acid".e-EROS Encyclopedia of Reagents for Organic Synthesis doi :10.1002/047084289X.rt254.pub2 .ISBN 978-0471936237 ^ Cooper, Mark S.;Heaney, Harry ; Newbold, Amanda J.; Sanderson, William R. (1990). "Oxidation Reactions Using Urea–Hydrogen Peroxide; A Safe Alternative to Anhydrous Hydrogen Peroxide".Synlett 1990 (9):533– 535.doi :10.1055/s-1990-21156 . ^ Hagen, Timothy J. (2007)."Prilezhaev reaction" . In Li, Jie Jack;Corey, E. J. (eds.).Name Reactions of Functional Group Transformations .John Wiley & Sons . pp. 274– 281.ISBN 9780470176504
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g.,brompheniramine ,buclizine ,captodiame ,chlorphenamine (chlorpheniramine) ,cinnarizine ,clemastine ,cyproheptadine ,dimenhydrinate ,dimetindene ,diphenhydramine ,doxylamine ,meclizine ,mequitazine ,perlapine ,phenindamine ,pheniramine ,phenyltoloxamine ,promethazine ,propiomazine ,triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g.,clozapine ,fluperlapine ,olanzapine (+fluoxetine ),rilapine ,quetiapine ,tenilapine ,zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol ,+indacaterol ,+neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,femoxetine ,paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g.,amitriptyline (+perphenazine ),amitriptylinoxide ,butriptyline ,cidoxepin ,clomipramine ,desipramine ,desmethyldesipramine ,dibenzepin ,dosulepin (dothiepin) ,doxepin ,imipramine ,lofepramine ,nitroxazepine ,northiaden (desmethyldosulepin) ,nortriptyline ,protriptyline ,quinupramine ,trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Tropine benzilate Trospium chloride Typical antipsychotics (e.g.,chlorpromazine ,chlorprothixene ,cyamemazine (cyamepromazine) ,loxapine ,mesoridazine ,thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (andprodrugs )
