Oxetane

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Oxetane
Oxetane.svg
Oxetane-from-xtal-3D-balls.png
Names
IUPAC name
Oxetane
Other names
1,3-propylene oxide
1,3-epoxypropane
oxacyclobutane
trimethylene oxide
Identifiers
503-30-0 YesY
ChEBI CHEBI:30965 N
ChemSpider 9994 N
Jmol-3D images Image
PubChem 10423
UNII I279Q16FU6 YesY
Properties
C3H6O
Molar mass 58.08 g·mol−1
Density 0.8930 g/cm3
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 noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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[edit]

A typical well-known method of preparation is the reaction of potassium hydroxide with 3-chloropropyl acetate at 150 °C:[1]

Synthesis of trimethylene oxide.png

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[edit]

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.[2] 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.[2]

See also[edit]

References[edit]

  1. ^ C. R. Noller (1955). "Trimethylene Oxide". Org. Synth. 29: 92. ; Coll. Vol. 3, p. 835 
  2. ^ a b 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>