Oxetane

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Oxetane
Oxetane.svg Oxetane-from-xtal-3D-balls.png
Identifiers
CAS number 503-30-0 YesY
UNII I279Q16FU6 YesY
ChEBI CHEBI:30965
Jmol-3D images Image 1
Properties
Molecular formula C3H6O
Molar mass 58.08 g mol−1
Density 0.8930 g/cm3
Boiling point 49–50 °C
Hazards
Flash point −19.0 °F (NTP, 1992)
Except where noted otherwise, 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[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: 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>