Oxetane
Title: Oxetane
Subject: Heterocyclic compound, Prins reaction, Structural isomer, Mukaiyama Taxol total synthesis, Wender Taxol total synthesis
Collection: Oxetanes
1,3-propylene oxide
1,3-epoxypropane
oxacyclobutane
trimethylene oxide
CAS number Y
ChemSpider N
UNII Y
ChEBI N
Jmol-3D images Image 1
C1CCO1
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
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)
Flash point −28.3 °C; −19.0 °F; 244.8 K (NTP, 1992)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N Y/ N?)
Oxetane, or 1,3-propylene oxide, is an oxygen atom.
The term oxetane may also refer more generally to any organic compound containing an oxetane ring.
Production 1
Taxol 2
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]
β-Propiolactone or 2-oxetanone.
3-Oxetanone
^ C. R. Noller (1955), "Trimethylene Oxide",
^ 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
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Oxetanes
Database, Chemistry, PubMed, American Chemical Society, National Center for Biotechnology Information
Royal Society of Chemistry, Semantic web, Peer review, Dictionary, Raleigh, North Carolina
United Kingdom, Research center, Ontology (information science), Ion, Nucleic acids
Water, Gold, Mass, Osmium, Iridium
Florida State University, United States, Bristol-Myers Squibb, Total synthesis, Food and Drug Administration
Heterocyclic compound
Tin, Nitrogen, Oxygen, Sulfur, Boron
Prins reaction
Chemistry, Aldehyde, Alkene, Nucleophile, Formaldehyde
Structural isomer
Alcohol, Carbon, Oxygen, Hydrogen, Infrared
Mukaiyama Taxol total synthesis
Pyridine, Sodium, Aldol reaction, Acetate, Alcohol
Wender Taxol total synthesis
Bromine, Alcohol, Hydrogen, Pyridine, Digital object identifier