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Oxetane

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Title: Oxetane  
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Subject: Heterocyclic compound, Prins reaction, Structural isomer, Mukaiyama Taxol total synthesis, Wender Taxol total synthesis
Collection: Oxetanes
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Oxetane

Oxetane
Identifiers
CAS number  YesY
PubChem
ChemSpider  N
UNII  YesY
ChEBI  N
Jmol-3D images Image 1
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 are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/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.

Contents

  • Production 1
  • Taxol 2
  • See also 3
  • References 4

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

References

  1. ^ C. R. Noller (1955), "Trimethylene Oxide",  
  2. ^ 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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