Oxetane

Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula C
3H
6O, having a four-membered ring with three carbon atoms and one oxygen atom.

Oxetane
Names
Preferred IUPAC name
Oxetane[1]
Systematic IUPAC name
1,3-Epoxypropane
Oxacyclobutane
Other names
1,3-Propylene oxide
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
Melting point −97 °C (−143 °F; 176 K)
Boiling point 49 to 50 °C (120 to 122 °F; 322 to 323 K)
1.3895 at 25°C
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 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

The term "an oxetane" or "oxetanes" refer to any organic compound containing the 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]

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gollark: This is me: http://www.murderousmaths.co.uk/miscpix/golplassm.gif
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gollark: The policy is very clear.
gollark: > You agree that your mind, thoughts, soul and other distinguishing characteristics may be repurposed/utilized at any time for the training of GPT-██ or other artificial intelligences at the discretion of the PotatOS Advanced Projects team. You also agree that your soul may be temporarily[6] be placed into various apioformic entities (see Appendix 6.7) for various purposes³. You can opt out of this by being soulless and an empty husk of what you once were. You are permitted to maintain consciousness as long as this does not negatively affect PotatOS™ operations. You agree that you either are a robot or may be converted into one if it is deemed necessary.

See also

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". Organic Syntheses. 29: 92.; Collective Volume, 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>
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