Azetidine

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Not to be confused with azatadine.
Azetidine
Azetidine structure.svg
Azetidine3d.png
Names
Preferred IUPAC name
Azetidine[1]
Systematic IUPAC name
Azacyclobutane
Other names
Azetane
Trimethylene imine
1,3-Propylenimine
Identifiers
3D model (JSmol)
102384
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.240 Edit this at Wikidata
EC Number
  • 207-963-8
986
UNII
Properties
C3H7N
Molar mass 57.09 g/mol
Appearance colorless liquid
Density 0.847 g/cm3 at 25 °C
Boiling point 61 to 62 °C (142 to 144 °F; 334 to 335 K)
miscible
Acidity (pKa) 11.29 (conjugate acid; H2O)[2]
Hazards
Main hazards Somewhat strong base, combustible
GHS pictograms GHS02: FlammableGHS05: Corrosive
GHS Signal word Danger
GHS hazard statements
 H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, 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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Infobox references

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[]

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 "AlClH2" and "AlCl2H".[3] Azetidine can also be produced by a multistep route from 3-amino-1-propanol.[4]

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.[citation needed]

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.[5]

See also[]

  • Azete, the unsaturated analog

References[]

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 147. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  3. ^ Alcaide, Benito; Almendros, Pedro; Aragoncillo, Cristina (2007). "Β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products". Chemical Reviews. 107 (11): 4437–4492. doi:10.1021/cr0307300. PMID 17649981.
  4. ^ Donald H. Wadsworth (1973). "Azetidine". Organic Syntheses. 53: 13. doi:10.15227/orgsyn.053.0013.
  5. ^ Kovács, Ervin; Ferenc, Faigl; Zoltan, Mucsi (Aug 10, 2020). "Regio- and Diastereoselective Synthesis of 2-Arylazetidines. Quantum Chemical Explanation of Baldwin's Rules for the Ring-formation Reactions of Oxiranes". Journal of Organic Chemistry. doi:10.1021/acs.joc.0c01310. Retrieved Aug 10, 2020.

External links[]


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