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 model Interactive image
PubChem 10423
UNII I279Q16FU6 YesY
Properties
C3H6O
Molar mass 58.08 g/mol
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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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>