Isoxazolidine

Isoxazolidine
Identifiers
CAS Number
  • 504-72-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:50311
ChemSpider
  • 120107
PubChem CID
  • 136333
CompTox Dashboard (EPA)
  • DTXSID90198445 Edit this at Wikidata
InChI
  • InChI=1S/C3H7NO/c1-2-4-5-3-1/h4H,1-3H2
    Key: CIISBYKBBMFLEZ-UHFFFAOYSA-N
  • C1CNOC1
Properties
Chemical formula
 C3H7NO
Molar mass 73.095 g·mol−1
Appearance colorless liquid
Boiling point 59 °C (138 °F; 332 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Isoxazolidine is the organic compound with the formula (CH2)3(NH)O. It is the parent of a family of compounds called Isoxazolidines, which are saturated C3NO heterocyclic rings where the nitrogen and oxygen occupy adjacent positions (1 and 2). They are the saturated analogues of Isoxazoles, and they are isomeric with oxazolidines, where the N and O are separated by one carbon.[1]

Isoxazolidines can be produced by the nitrone-olefin (3+2) cycloaddition reaction.

They represent precursors to 1,3-aminoalcohols.[2] The series Organic Syntheses provides detailed procedures that yield isoxazolidines, e.g., from styrene[3] and N-phenylmaleimide.[4] Some isoxazolidines are of medicinal interest.[5]

References

  1. ^ Cordero, Franca M.; Giomi, Donatella; Lascialfari, Luisa (2013). Five-Membered Ring Systems. Progress in Heterocyclic Chemistry. Vol. 25. pp. 291–317. doi:10.1016/B978-0-08-099406-2.00012-1. ISBN 9780080994062.
  2. ^ Frederickson, Martyn (1997). "Optically active isoxazolidines via asymmetric cycloaddition reactions of nitrones with alkenes: Applications in organic synthesis". Tetrahedron. 53 (2): 403–425. doi:10.1016/S0040-4020(96)01095-2.
  3. ^ Brüning, Ingrid; Grashey, Rudolf; Hauck, Hans; Huisgen, Rolf; Seidl, Helmut (1966). "2,3,5-Triphenylisoxazolidine". Organic Syntheses. 46: 127. doi:10.15227/orgsyn.046.0127.
  4. ^ Brüning, Ingrid; Grashey, Rudolf; Hauck, Hans; Huisgen, Rolf; Seidl, Helmut (1966). "2-phenyl-3-n-propylisoxazolidine-4,5-cis-dicarboxylic acid n-phenylimide". Organic Syntheses. 46: 96. doi:10.15227/orgsyn.046.0096.
  5. ^ Berthet, Mathéo; Cheviet, Thomas; Dujardin, Gilles; Parrot, Isabelle; Martinez, Jean (2016). "Isoxazolidine: A Privileged Scaffold for Organic and Medicinal Chemistry". Chemical Reviews. 116 (24): 15235–15283. doi:10.1021/acs.chemrev.6b00543. PMID 27981833.