| 词条 | Oxetane |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444037024 | ImageFileL1 = Oxetane.svg | ImageFileR1 = Oxetane-from-xtal-3D-balls.png | PIN = Oxetane[1] | OtherNames = 1,3-Propylene oxide 1,3-Epoxypropane Oxacyclobutane Trimethylene oxide |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 503-30-0 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 30965 | PubChem = 10423 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 9994 | InChI = 1/C3H6O/c1-2-4-3-1/h1-3H2 | InChIKey = AHHWIHXENZJRFG-UHFFFAOYAE | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C3H6O/c1-2-4-3-1/h1-3H2 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = AHHWIHXENZJRFG-UHFFFAOYSA-N | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I279Q16FU6 | UNNumber = 1280 | Beilstein = 102382 | Gmelin = 239520 | EINECS = 207-964-3 | SMILES = C1CCO1 |Section2={{Chembox Properties | C=3 | H=6 | O=1 | MolarMass = 58.08 g/mol | Appearance = | Density = 0.8930 g/cm3 | MeltingPt = | BoilingPtC = 49 to 50 | BoilingPt_notes = | Solubility = | RefractIndex = 1.3895 at 25°C |Section3={{Chembox Hazards | MainHazards = | FlashPtF = −19.0 | FlashPt_notes = (NTP, 1992) | AutoignitionPt = | GHSPictograms = {{GHS02}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|225|302|312|332}} | PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|270|271|280|301+312|302+352|303+361+353|304+312|304+340|312|322|330|363|370+378|403+235|501}} }} Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula {{chem|C|3|H|6|O}}, having a four-membered ring with three carbon atoms and one oxygen atom. The term "a oxetane" or "oxetanes" refer to any organic compound containing the oxetane ring. ProductionA typical well-known method of preparation is the reaction of potassium hydroxide with 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. 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. TaxolPaclitaxel (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]{{clear|left}}See also
References1. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 147 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}} 2. ^{{OrgSynth| author =C. R. Noller| year =1955| title =Trimethylene Oxide| volume =29| pages =92| collvol =3| collvolpages =835| prep =CV3P0835}} 3. ^1 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 1 : Oxetanes |
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