Thiazoline

Thiazoline
Names
IUPAC names
2,3-Dihydrothiazole
2,5-Dihydrothiazole
4,5-Dihydrothiazole
Other names
2,3-Dihydro-1,3-thiazole or 4-thiazoline
2,5-Dihydro-1,3-thiazole or 3-thiazoline
4,5-Dihydro-1,3-thiazole or 2-thiazoline
Identifiers
3D model (JSmol)
ChemSpider
  • (2,3): InChI=1S/C3H5NS/c1-2-5-3-4-1/h1-2,4H,3H2
    Key: OYJGEOAXBALSMM-UHFFFAOYSA-N
  • (2,5): InChI=1S/C3H5NS/c1-2-5-3-4-1/h1H,2-3H2
    Key: JLPUISACQXFVRC-UHFFFAOYSA-N
  • (4,5): InChI=1S/C3H5NS/c1-2-5-3-4-1/h3H,1-2H2
    Key: CBDKQYKMCICBOF-UHFFFAOYSA-N
  • (2,3): C1=CSCN1
  • (2,5): C1=NCSC1
  • (4,5): C1CSC=N1
Properties
C3H5NS
Molar mass 87.14 g·mol−1
Appearance Colorless liquids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiazolines (/θaɪˈæzoʊliːnz/; or dihydrothiazoles) are a group of isomeric 5-membered heterocyclic compounds containing both sulfur and nitrogen in the ring. Although unsubstituted thiazolines are rarely encountered themselves, their derivatives are more common and some are bioactive. For example, in a common post-translational modification, cysteine residues are converted into thiazolines.[1]

The name thiazoline originates from the Hantzsch–Widman nomenclature.

  1. ^ Walsh, Christopher T.; Nolan, Elizabeth M. (2008). "Morphing peptide backbones into heterocycles". Proceedings of the National Academy of Sciences USA. 105 (15): 5655–5656. Bibcode:2008PNAS..105.5655W. doi:10.1073/pnas.0802300105. PMC 2311349. PMID 18398003.