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2-sec-Butyl-4,5-dihydrothiazole

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2-sec-Butyl-4,5-dihydrothiazole
Names
Preferred IUPAC name 2-(Butan-2-yl)-4,5-dihydro-1,3-thiazole
Other names SBT

2-(1-methylpropyl)-2-thiazoline

2-sec-butyl-2-thiazoline
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3Key: SAWWKXMIPYUIBW-UHFFFAOYSA-N
  • InChI=1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3Key: SAWWKXMIPYUIBW-UHFFFAOYSA-N
SMILES
  • CCC(C)C1=NCCS1
Properties
Chemical formula C7H13NS
Molar mass 143.25 g·mol
Density 1.06 g/cm
Boiling point 193 °C (379 °F; 466 K)
Hazards
Flash point 70.5 °C (158.9 °F; 343.6 K)
Related compounds
Related compounds Dihydrothiazole (thiazoline)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2-sec-Butyl-4,5-dihydrothiazole (also known as SBT) is a thiazoline compound with the molecular formula C7H13NS. A volatile pheromone found in rodents such as mice and rats, SBT is excreted in the urine and promotes aggression amongst males while inducing synchronized estrus in females.

Binding to MUP

Mouse major urinary proteins (MUPs) are responsible for binding to hydrophobic ligands such as the pheromone SBT. SBT binds within MUP-I's barrel-shaped active site, forming a hydrogen bond with a water molecule within the active site, which in turn is stabilized by forming hydrogen bonds with residue Phe56 and another water molecule; this second water molecule also forms hydrogen bonds to residues in the active site, namely Leu58 and Thr39. SBT also forms van der Waals forces with several of MUP-I's residues, including Ala121, Leu123, Leu134, Leu72, Val100, and Phe108.

When bound, MUP safely carries SBT through the aqueous environment; once the protein-ligand complex is excreted in the urine, MUP helps prevent SBT decomposition and controls the slow release of SBT over a prolonged period of time, resulting in the physiological and behavioral responses of animals who come into contact with the pheromone.

Synthesis

SBT can be produced from 3-(2-aminoethanethio)-4-methylhex-2-enenitrile; however, it is also possible to synthesize SBT from ethanolamine and 2-methylbutanoic acid, using Lawesson's reagent and microwave irradiation.

References

  1. CID 162148 from PubChem
  2. Perez-Miller, Samantha; Zou, Qin; Novotny, Milos V.; Hurley, Thomas D. (2010). "High resolution X-ray structures of mouse major urinary protein nasal isoform in complex with pheromones". Protein Science. 19 (8): 1469–79. doi:10.1002/pro.426. PMC 2923500. PMID 20509168.
  3. Timm, David E.; Baker, L.J.; Mueller, Heather; Zidek, Lukas; Novotny, Milos V. (2001). "Structural basis of pheromone binding to mouse major urinary protein (MUP-I)". Protein Science. 10 (5): 997–1004. doi:10.1110/ps.52201. PMC 2374202. PMID 11316880.
  4. Landor, S (1984). "Allenes-41 the addition of thiols to allenyl- and phenylpropynyl- nitrile and the formation of thiazolines and benzothiazoles". Tetrahedron. 40 (11): 2141. doi:10.1016/S0040-4020(01)88457-X.
  5. Seijas, Julio A.; Vázquez-Tato, M. Pilar; Crecente-Campo, José (2008). "Straightforward microwave-assisted synthesis of 2-thiazolines using Lawesson's reagent under solvent-free conditions". Tetrahedron. 64 (39): 9280. doi:10.1016/j.tet.2008.07.027.
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