Oxetane

Oxetane

Names
IUPAC name Oxetane
Other names 1,3-propylene oxide 1,3-epoxypropane oxacyclobutane trimethylene oxide
Identifiers
CAS Registry Number	503-30-0 Y
ChEBI	CHEBI:30965 N
ChemSpider	9994 N
InChI InChI=1S/C3H6O/c1-2-4-3-1/h1-3H2 N Key: AHHWIHXENZJRFG-UHFFFAOYSA-N N InChI=1/C3H6O/c1-2-4-3-1/h1-3H2 Key: AHHWIHXENZJRFG-UHFFFAOYAE
Jmol-3D images	Image
PubChem	10423
SMILES C1CCO1
UNII	I279Q16FU6 Y
Properties
Molecular formula	C3H6O
Molar mass	58.08 g·mol−1
Density	0.8930 g/cm3
Boiling point	49 to 50 °C (120 to 122 °F; 322 to 323 K)
Hazards
Flash point	−28.3 °C; −19.0 °F; 244.8 K (NTP, 1992)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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

A typical well-known method of preparation is the reaction of potassium hydroxide with 3-chloropropyl acetate at 150 °C:^[1]

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.^[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

• β-Propiolactone or 2-oxetanone.
• 3-Oxetanone

References