Oxetane

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Oxetane
Oxetane.svg
Oxetane-from-xtal-3D-balls.png
Names
Preferred IUPAC name
Oxetane[1]
Other names
1,3-Propylene oxide
1,3-Epoxypropane
Oxacyclobutane
Trimethylene oxide
Identifiers
3D model (JSmol)
102382
ChEBI
ChemSpider
ECHA InfoCard 100.007.241
EC Number 207-964-3
239520
UNII
UN number 1280
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)
1.3895 at 25°C
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H225, H302, H312, H332
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+312, P302+352, P303+361+353, P304+312, P304+340, P312, P322, P330, P363, P370+378, P403+235, P501
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 a heterocyclic organic compound with the molecular formula C
3
H
6
O
, 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:[2]

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.[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[edit]

References[edit]

  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". Organic Syntheses. 29: 92.; Collective Volume, 3, p. 835
  3. ^ 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>