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.
| Names | |
|---|---|
| Preferred IUPAC name Oxetane[1] | |
| Systematic IUPAC name 1,3-Epoxypropane Oxacyclobutane | |
| Other names 1,3-Propylene oxide Trimethylene oxide |
A typical well-known method of preparation is the reaction of potassium hydroxidewith 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.
Another 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.
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]
https://en.wikipedia.org/wiki/Oxetane
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