Tetrahydrothiophen-3-ones

The above solution was added to tetrahydrothiophen-3-one (10.2 g, lOOmmol) in TBME (35 mL) and the resulting mixture was stirred until an emulsion formed. 

By an improved solid-phase extraction procedure, 2-methyl-tetrahydro-furan-3-thiol 77 could be measured in wine at levels of 0.2 ng/L (01MI533, 08JC(A)9). This compound smells like strongly cooked meat, described as roasted meaty. From grape cultivars of the Vinho Verde region in Portugal 2-methyl-tetrahydrothiophen-3-one 78 was isolated (02ACA157). 

Thiophenes thiophene tetrahydrothiophene-3-one 2-butylthiophene 2-formy1-3-methylthiophene 2-pentylthiophene 2-hexylthiophene 2-heptylthiophene 2-formyl-5(or 3)-pentylthiophene 3.5 10.5 57.2 29.8 13.1 42.0 1.8 15.6... 

Finally, some miscellaneous fused systems containing thiophene rings have attracted some interest. The electrophilic chemistry of several thia-PHAs has been investigated, among others benzo[Z>]naphtho[2,l-c/]thiophene , whereas an approach to related partially saturated systems from tetrahydrothiophene-3-one has been published <07TL4715>. It should also be mentioned that a 4-armno-7-ar ithieno 3,2-<7 pyrimidine library has been prepared <07JCC431>. 

Tetrahydrothiophene-3-one reacts with 6-aryl-2//-pyran-2-ones in the presence of base to give dihydrobenzothio-phene (Equation 74). The reaction proceeds through the addition of the carbanion generated from tetrahydrothiophene-3-one to pyran-2-one followed by base-induced intramolecular annulation <2001JOC5333, 2002J(P1)1426>. 

Metfaylbutanal Dimethyl trisulfide Methional Tetrahydrothiophen-3-one (Stimulus) (Putrid) (Potato-like) (Roasty)... 

J.24) 3(2/f)-Thiophenone, dihydro-, tetrahydrothiophen-3-one, thiolan-3-one, thiophan-3-one [1003-04-9] FEMA 3266... 

Thiophene-3-one 104 has been shown to undergo conversion to the benzo[Z)]thiophene derivatives 105 upon treatment with the pyran-2-ones 106 <04BMC1543>, A convenient transformation of tetrahydrothiophene-3-one to tetrahydrothiophene-3-one-1,1-dioxide has also been reported <04SC567>. 

Wong,)., Huisman, G., Tfuesdell, S., and Lalonde, (. (2010) Highly enantioselective reduction of a small heterocyclic ketone biocatalytic reduction of tetrahydrothiophene-3-one to the corresponding (R)-alcohol. Org. Proc. Res. Dev., 14, 188-192. 

The same combined enzymatic concept was also useful for the enantioselective reduction of tetrahydrothiophene-3-one 7 to afford a useful building block for the pharmaceutical synthesis of sulopenem 9, a potent antibacterial. The approach is synthetically very challenging, in light of the nearly spatially symmetrical ((3-CH2 vs. -S) ketone used as substrate (Scheme 36.5). Herein, to afford competitive figures in terms of productivities and selectivities, several rounds of directed evolution of the Lactobacillus kefir enzyme were conducted. The optimized process was successfully scaled up to 100 kg of product. 

---