Oxetane
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Names | |||
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Preferred IUPAC name
Oxetane[1] | |||
Systematic IUPAC name
1,3-Epoxypropane Oxacyclobutane | |||
Other names
1,3-Propylene oxide
Trimethylene oxide | |||
Identifiers | |||
3D model (JSmol)
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102382 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.007.241 | ||
EC Number |
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239520 | |||
PubChem CID
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UNII | |||
UN number | 1280 | ||
CompTox Dashboard (EPA)
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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) | ||
Refractive index (nD)
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1.3895 at 25°C | ||
Hazards | |||
GHS labelling: | |||
Signal word
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Danger | ||
H225, H302, H312, H332 | |||
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, 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). | |||
what is ?) | (|||
Infobox references | |||
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.
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 at 150 °C:[2]
Yield of oxetane made this way is c. 40%, as the synthesis can lead to a variety of by-products.
Another possible reaction to form an oxetane ring is the Paternò–Büchi reaction. The oxetane ring can also be formed through as well as through decarboxylation of a six-membered cyclic carbonate.
Taxol[]
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[]
- β-Propiolactone or 2-oxetanone.
- 3-Oxetanone
References[]
- ^ 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.
- ^ C. R. Noller (1955). "Trimethylene Oxide". Organic Syntheses. 29: 92.; Collective Volume, 3, p. 835
- ^ a b Willenbring, Dan; Tantillo, Dean J. (April 2008). "Mechanistic possibilities for oxetane formation in the biosynthesis of Taxol's D ring". Russian Journal of General Chemistry. 78 (4): 723–731. doi:10.1134/S1070363208040336. S2CID 98056619.
- Oxetanes