Oxetane

Oxetane

Names
Preferred IUPAC name Oxetane[1]
Other names 1,3-Propylene oxide 1,3-Epoxypropane Oxacyclobutane Trimethylene oxide
Identifiers
CAS Number	503-30-0
3D model (Jmol)	Interactive image
ChEBI	CHEBI:30965
ChemSpider	9994
ECHA InfoCard	100.007.241
PubChem	10423
UNII	I279Q16FU6
InChI InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2 Key: AHHWIHXENZJRFG-UHFFFAOYSA-N InChI=1/C3H6O/c1-2-4-3-1/h1-3H2 Key: AHHWIHXENZJRFG-UHFFFAOYAE
SMILES C1CCO1
Properties
Chemical formula	C3H6O
Molar mass	58.08 g/mol
Density	0.8930 g/cm^3
Boiling point	49 to 50 °C (120 to 122 °F; 322 to 323 K)
Hazards
Flash point	−28.3 °C; −19.0 °F; 244.8 K (NTP, 1992)
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

Oxetane, or 1,3-propylene oxide, is an heterocyclic organic compound with the molecular formula C₃H₆O, having a four-membered ring with three carbon atoms and one oxygen atom.

The term oxetane may also refer more generally to any organic compound containing an oxetane ring.

Production

A typical well-known method of preparation is the reaction of potassium hydroxide with 3-chloropropyl acetate at 150 °C:^[2]

Yield of oxetane made this way is c. 40%, as the synthesis can lead to a variety of by-products.

Other possible reactions to form oxetane ring is the Paternò–Büchi reaction. The oxetane ring can also be formed through diol cyclization as well as through decarboxylation of a six-membered cyclic carbonate.

Taxol

Paclitaxel with oxetane ring at right.

Paclitaxel (Taxol) is an example of a natural product containing an oxetane ring. Taxol has become a major point of interest among researchers due to its unusual structure and success in the involvement of cancer treatment.^[3] The attached oxetane ring is an important feature that is used for the binding of microtubules in structure activity; however little is known about how the reaction is catalyzed in nature, which creates a challenge for scientists trying to synthesize the product.^[3]

See also

• β-Propiolactone or 2-oxetanone.
• 3-Oxetanone

References

1. 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. C. R. Noller (1955). "Trimethylene Oxide". Org. Synth. 29: 92.; Coll. Vol., 3, p. 835
3. Willenbring, Dan, and Dean J. Tantillo.. "Mechanistic possibilities for oxetane formation in the biosynthesis of Taxol’s D ring." Russian Journal of General Chemistry 78.4 (Apr. 2008): 7237–31. Advanced Placement Source. EBSCO. [Library name], [City], [State abbreviation]. 22 Apr. 2009 <http://search.ebscohost.com/login.aspx?direct=true&db=aqh&AN=32154883&site=ehost-live>