Isoxazolidine

Isoxazolidine
Identifiers
CAS Number	504-72-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:50311;
ChemSpider	120107;
PubChem CID	136333;
CompTox Dashboard (EPA)	DTXSID90198445 ;
	InChI InChI=1S/C3H7NO/c1-2-4-5-3-1/h4H,1-3H2 Key: CIISBYKBBMFLEZ-UHFFFAOYSA-N;
	SMILES 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

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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

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