2-sec-Butyl-4,5-dihydrothiazole

2-sec-Butyl-4,5-dihydrothiazole^[1]

Names
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	56367-27-2
ChemSpider	142398
Jmol interactive 3D	Image
PubChem	162148
InChI InChI=1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3 Key: SAWWKXMIPYUIBW-UHFFFAOYSA-N InChI=1S/C7H13NS/c1-3-6(2)7-8-4-5-9-7/h6H,3-5H2,1-2H3 Key: SAWWKXMIPYUIBW-UHFFFAOYSA-N
SMILES CCC(C)C1=NCCS1
Properties
Chemical formula	C7H13NS
Molar mass	143.25 g·mol^−1
Density	1.06 g/cm^3
Boiling point	193 °C (379 °F; 466 K)
Hazards
Flash point	70.5 °C (158.9 °F; 343.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.^[2]

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. ^[3]

Synthesis

SBT can be produced from 3-(2-aminoethanethio)-4-methylhex-2-enenitrile;^[4] however, it is also possible to synthesize SBT from ethanolamine and 2-methylbutanoic acid, using Lawesson's reagent and microwave irradiation.^[5]

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.