Oxetane

Oxetane
Names
	Preferred IUPAC name Oxetane
	Systematic IUPAC name 1,3-Epoxypropane; Oxacyclobutane
	Other names 1,3-Propylene oxide; Trimethylene oxide
Identifiers
CAS Number	503-30-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	102382
ChEBI	CHEBI:30965 ;
ChemSpider	9994 ;
ECHA InfoCard	100.007.241
EC Number	207-964-3;
Gmelin Reference	239520
PubChem CID	10423;
UNII	I279Q16FU6 ;
UN number	1280
CompTox Dashboard (EPA)	DTXSID8025969 ;
	InChI InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2 Key: AHHWIHXENZJRFG-UHFFFAOYSA-N ; InChI=1/C3H6O/c1-2-4-3-1/h1-3H2 Key: AHHWIHXENZJRFG-UHFFFAOYAE;
	SMILES C1CCO1;
Properties
Chemical formula	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)	1.3895 at 25°C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H332
Precautionary statements	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). verify (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 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.

Anotherer possible reaction to form an 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 (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]

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; Collected Volumes, vol. 3, p. 835.
^ ^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>

[iupac2013-1] 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; Collected Volumes, vol. 3, p. 835.

[WillenbringDan-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>

[1]

[2]

[3]

Production

Taxol

See also

References