89820-00-8

Usage

Uses

Used in Organic Synthesis:
3-octylthio-1,1,1-trifluoro-2-propanone is used as a reagent in organic synthesis for its unique chemical properties, enabling the creation of complex organic molecules.
Used in Pharmaceutical Industry:
3-octylthio-1,1,1-trifluoro-2-propanone is used as a precursor in the preparation of various pharmaceuticals, leveraging its lipophilic properties to enhance membrane permeability in drug formulations.
Used in Agrochemical Industry:
3-octylthio-1,1,1-trifluoro-2-propanone is utilized as a precursor in the synthesis of agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used in Specialty Chemicals Production:
This chemical is used in the production of specialty chemicals, highlighting its importance in various industrial applications.
Used in Drug Discovery:
3-octylthio-1,1,1-trifluoro-2-propanone serves as an important intermediate in the discovery of new drug candidates, playing a crucial role in advancing pharmaceutical research and development.

InChI:InChI=1/C11H19F3OS/c1-2-3-4-5-6-7-8-16-9-10(15)11(12,13)14/h2-9H2,1H3

Upstream product

• 3698-95-1 methyl octyl sulfide 
• 383-63-1 ethyl trifluoroacetate, 
• 431-35-6 3-bromo-1,1,1-trifluoroacetone 
• 111-88-6 Octanethiol 

Relevant academic research and scientific papers

New fluorinated derivatives as esterase inhibitors. Synthesis, hydration and crossed specificity studies

A variety of new fluorinated chemicals have been prepared for the first time and tested as inhibitors of esterases, one of the main enzymes involved in pheromone catabolism, in two economically important pests, the Egyptian armyworm Spodoptera littoralis (SL) and the Mediterranean corn borer Sesamia nonagrioides (SN). Using the respective major component of the pheromone as substrate, the Km and Vmax of the antennal esterase of both insects resulted to be 5.66×10-4 M and 8.47×10-6 Mmin-1 for SL and 1.61×10-7 M and 1.25×10-7 Mmin-1 for SN, pointing out that SN esterase has a higher affinity for its corresponding substrate than SL. In general, the trifluoromethyl ketones (TFMKs) exhibited higher inhibitory potency than the corresponding difluoromethyl ketones (DFMKs) or difluoroaldehydes (DFAs). The compounds appeared to hydrate differently in aqueous solution, the extent of hydration following the order: α,α-DFMKshyd and the inhibitory potency and no specificity has been found when the chemicals were assayed on extracts of both insects.

Synthesis of new carboxylesterase inhibitors and evaluation of potency and water solubility

Carboxylesterases are essential enzymes in the hydrolysis and detoxification of numerous pharmaceuticals and pesticides. They are vital in mediating organophosphate toxicity and in activating many prodrugs such as the chemotherapeutic agent CPT-11. It is therefore important to study the catalytic mechanism responsible for carboxylesterase-induced hydrolysis, which can be accomplished through the use of potent and selective inhibitors. Trifluoromethyl ketone (TFK)-containing compounds are the most potent esterase inhibitors described to date. The inclusion of a thioether moiety β to the carbonyl further increased TFK inhibitor potency. In this study, we have synthesized the sulfone analogues of a series of aliphatic and aromatic substituted thioether TFKs to evaluate their potency and solubility properties. This structural change shifted the keto/hydrate equilibrium from 95% hydrate, forming almost exclusively the gem-diol. These new compounds were evaluated for their inhibition of carboxylesterase activity in three different systems, rat liver microsomes, commercial porcine esterase, and juvenile hormone esterase in cabbage looper (Trichoplusia ni) hemolymph. The most potent inhibitor of rat liver carboxylesterase activity was 1,1,1-trifluoro-3-(decane-1-sulfonyl)-propan-2,2-diol, which inhibited 50% of the enzyme activity (IC50) at 6.3 ± 1.3 nM and was 18-fold more potent than its thioether analogue. However, the sulfone derivatives were consistently poorer inhibitors of porcine carboxylesterase activity and juvenile hormone esterase activity, with IC50 values ranging from low micromolar to millimolar. The compound 1,1,1-trifluoro-3-(octane-1-sulfonyl)-propan-2,2-diol was shown to have a 10-fold greater water solubility than its thioether analogue, 1,1,1-trifluoro-3-octylsulfanyl-propan-2-one (OTFP). These novel compounds provide further evidence of the differences between esterase orthologs, suggesting that additional development of esterase inhibitors may ultimately provide a battery of ortholog and/or isoform selective inhibitors analogous to those available for other complex enzyme families with overlapping substrate specificity.

Asymmetric reduction of trifluoromethyl ketones containing a sulfur functionality by the alcohol dehydrogenase from Geotrichum

The reduction of trifluoromethyl ketones containing a sulfur functionality by the crude alcohol dehydrogenase from Geotrichum proceeded successfully, and the corresponding optically active alcohols were synthesized with high yields and excellent enantiose