Azetidine

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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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-963-8
986
PubChem CID
UNII
  • InChI=1S/C3H7N/c1-2-4-3-1/h4H,1-3H2 Yes check.svgY
    Key: HONIICLYMWZJFZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H7N/c1-2-4-3-1/h4H,1-3H2
    Key: HONIICLYMWZJFZ-UHFFFAOYAE
  • N1CCC1
Properties
C3H7N
Molar mass 57.09 g/mol
Appearancecolorless 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
Occupational safety and health (OHS/OSH):
Main hazards
Somewhat strong base, combustible
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Related compounds
Other anions
Oxetane, Phosphetane, Thietane
Related compounds
 Aziridine, Diazetidine, Pyrrolidine, Piperidine, Azepane, Azocane, Azonane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Synthesis and occurrence

Mugineic acid, an iron-binding azetidine. MugineicAcid.svg
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 "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 ]

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. [5]

See also

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. 85 (17): 11226–11239. doi: 10.1021/acs.joc.0c01310 . PMC   7498157 . PMID   32786621.
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