Oxetane
Encyclopedia
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.
with 3-chloropropyl acetate at 150°C
Yield of oxetane made this way is ca. 40%, as the synthesis can lead to a variety of by-products.
Other possible reactions to form oxetane ring is the Paternò–Büchi reaction. Also, diol cyclization can form oxetane ring.
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. 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 reaction.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the molecular formula C3H6O, having a four-membered ring with three carbon atoms and one oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
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 hydroxidePotassium hydroxide
Potassium hydroxide is an inorganic compound with the formula KOH, commonly called caustic potash.Along with sodium hydroxide , this colorless solid is a prototypical strong base. It has many industrial and niche applications. Most applications exploit its reactivity toward acids and its corrosive...
with 3-chloropropyl acetate at 150°C
Yield of oxetane made this way is ca. 40%, as the synthesis can lead to a variety of by-products.
Other possible reactions to form oxetane ring is the Paternò–Büchi reaction. Also, diol cyclization can form oxetane ring.
Taxol
Paclitaxel
Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It was discovered in a U.S. National Cancer Institute program at the Research Triangle Institute in 1967 when Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia and named it taxol...
(Taxol) is an example of a natural product
Natural product
A natural product is a chemical compound or substance produced by a living organism - found in nature that usually has a pharmacological or biological activity for use in pharmaceutical drug discovery and drug design...
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. 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 reaction.