{{distinguish|azatadine}} {{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443410972 | ImageFileL1 = Azetidine structure.svg | ImageSizeL1 = 100px | ImageFileR1 = Azetidine3d.png | ImageSizeR1 = 100px | PIN= Azetidine<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 147 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> | SystematicName = Azacyclobutane | OtherNames = Azetane<br />Trimethylene imine<br />1,3-Propylenimine |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9993 | InChI = 1/C3H7N/c1-2-4-3-1/h4H,1-3H2 | InChIKey = HONIICLYMWZJFZ-UHFFFAOYAE | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H7N/c1-2-4-3-1/h4H,1-3H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HONIICLYMWZJFZ-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 503-29-7 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 2171713 | PubChem = 10422 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 30968 | EC_number = 207-963-8 | UNII = 37S883XDWR | Gmelin = 986 | Beilstein = 102384 | SMILES = N1CCC1 }} |Section2={{Chembox Properties | Formula = | C=3 | H=7 | N=1 | MolarMass = 57.09 g/mol | Appearance = colorless liquid | Density = 0.847 g/cm<sup>3</sup> at 25 °C | MeltingPt = | BoilingPtC = 61 to 62 | BoilingPt_notes = | pKa = 11.29 (conjugate acid; H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 978-1498754286 | pages=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref> | Solubility = miscible }} |Section3={{Chembox Hazards | MainHazards = Somewhat strong base, combustible | FlashPt = | AutoignitionPt = | GHSPictograms = {{GHS02}}{{GHS05}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|314}} | PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|403+235|405|501}} }} |Section8={{Chembox Related | OtherCompounds = Aziridine, Diazetidine, Pyrrolidine, Piperidine, Azepane, Azocane, Azonane | OtherAnions = Oxetane, Phosphetane, Thietane }} }}
'''Azetidine''' is a saturated heterocyclic organic compound containing three carbon atoms and one nitrogen atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly basic compared to most secondary amines.
==Synthesis and occurrence== [[File:MugineicAcid.svg|thumb|left|220px|Mugineic acid, an iron-binding azetidine.]] Azetidines can be prepared by reduction of azetidinones (β-lactams) with lithium aluminium hydride. Even more effective is a mixture of lithium aluminium hydride and aluminium trichloride, a source of "AlClH<sub>2</sub>" and "AlCl<sub>2</sub>H".<ref>{{cite journal |doi=10.1021/cr0307300 |title=Β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products |year=2007 |last1=Alcaide |first1=Benito |last2=Almendros |first2=Pedro |last3=Aragoncillo |first3=Cristina |journal=Chemical Reviews |volume=107 |issue=11 |pages=4437–4492 |pmid=17649981}}</ref>
Azetidine can also be produced by a multistep route from 1,3-disubstituted alkanes. Thus, for example, a multistep route builds azetidine from 3-amino-1-propanol, acrylic acid, thionyl chloride, and base;<ref>{{cite journal |doi=10.15227/orgsyn.053.0013 |title=Azetidine |journal=Organic Syntheses |year=1973 |volume=53 |page=13 |author=Donald H. Wadsworth}}</ref> likewise, azetidine dicarboxylic acids form when glutaric anhydride is brominated (at the α position) and then aminated.<ref>{{cite journal|doi=10.1021/jm00168a007|title=Synthesis and bioactivity of a new class of rigid glutamate analogues|first1=Alan P.|last1=Kozikowski|first2=Werner|last2=Tückmantel|first3=Ian J.|last3=Reynolds|first4=Jarda T.|last4=Wroblewski|year=1990|publisher=American Chemical Society|journal=Journal of Medicinal Chemistry|volume=33|issue=6|p=1563}}</ref>
Regio- and diastereoselective synthesis of 2-arylazetidines could be performed from appropriately substituted oxiranes via ring transformation. It is controlled by Baldwin's Rules with remarkable functional group tolerance.<ref>{{cite journal |last1=Kovács |first1=Ervin |last2=Ferenc |first2=Faigl |last3=Zoltan |first3=Mucsi |title=Regio- and Diastereoselective Synthesis of 2-Arylazetidines. Quantum Chemical Explanation of Baldwin's Rules for the Ring-formation Reactions of Oxiranes. |journal=Journal of Organic Chemistry |date=Aug 10, 2020 |volume=85 |issue=17 |pages=11226–11239 |doi=10.1021/acs.joc.0c01310|pmid=32786621 | pmc=7498157 |doi-access=free }}</ref>
The Paternò−Büchi reaction has an ''aza'' analogue.
Azetidine and its derivatives are relatively rare structural motifs in natural products. They are a component of mugineic acids and penaresidins. Perhaps the most abundant azetidine containing natural product is azetidine-2-carboxylic acid - a toxic mimic of proline.{{cn|date=February 2021}}
== See also == * Azete, the unsaturated analog
==References== {{Reflist}}
==External links== * [http://www.chemsynthesis.com/base/chemical-structure-13241.html ChemSynthesis]
Category:Azetidines