Category: 2240-88-2

Liu, Jingping published the artcileFree-Radical-Promoted Dehydrogenative Coupling of Polyfluorinated Alcohol with Quinone, Chromone, and Coumarin, Name: 3,3,3-Trifluoropropan-1-ol, the publication is Organic Letters (2020), 22(12), 4844-4847, database is CAplus and MEDLINE.

A free-radical-mediated dehydrogenative cross-coupling reaction of polyfluorinated alc. with quinone, coumarin, and chromone was developed. It provides a sustainable and practical strategy for installation of fluorine atom into organic mols. by using polyfluorinated alcs.

Organic Letters published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Name: 3,3,3-Trifluoropropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Mao, Jialin published the artcileSynthesis and antituberculosis activity of novel mefloquine-isoxazole carboxylic esters as prodrugs, Formula: C3H5F3O, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(3), 1263-1268, database is CAplus and MEDLINE.

Previously, isoxazole I [R = EtO (II)] was reported to have excellent antituberculosis activity against both replicating and non-replicating Mycobacterium tuberculosis, with a min. inhibitory concentration (MIC) of 0.9 μM and 12.2 μM, resp. In this study, the antituberculosis activity of II was further investigated. Its activity appeared to be very specific for organisms of the M. tuberculosis complex and it effected significant reductions of bacterial numbers in infected macrophages with an EC₉₀ of 4.1 μM. More importantly, the increased in vitro antituberculosis activity of the corresponding acid I (R = HO) at pH 6.0 suggested that it may be active in vivo in an acidic environment produced as a consequence of inflammation in the lungs of TB patients. The fact that various ester bioisosteres of compound II lost anti-TB activity further suggested that II may function as a prodrug. The detailed structure-activity relationships (SARs) from this study should facilitate our ultimate goal of improving the anti-TB potency of this isoxazole ester series.

Bioorganic & Medicinal Chemistry Letters published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Formula: C3H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Jana, Sripati published the artcilePhotoinduced Proton-Transfer Reactions for Mild O-H Functionalization of Unreactive Alcohols, Product Details of C3H5F3O, the publication is Angewandte Chemie, International Edition (2020), 59(14), 5562-5566, database is CAplus and MEDLINE.

Hexafluoroisopropanol is typically considered as an unreactive solvent and not as a reagent in organic synthesis. Herein, we report on a mild and efficient photochem. reaction of aryl diazoacetates with hexafluoroisopropanol that enables, under stoichiometric reaction conditions, the synthesis of fluorinated ethers in excellent yield. Mechanistic studies indicate there is a preorganization of hexafluoroisopropanol and the diazoalkane acts as an unreactive hydrogen-bonding complex. Only after photoexcitation does this complex undergo a protonation-substitution reaction to the reaction product. Investigations on the applicability of this photochem. transformation show that a broad variety of acidic alcs. can be subjected to this transformation and thus demonstrate the feasibility of this concept for O-H functionalization reactions (54 examples, up to 98% yield).

Angewandte Chemie, International Edition published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Product Details of C3H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Morino, Yusuke published the artcileCu/N-Oxyl-catalyzed aerobic oxidative esterification to oxalic acid diesters from ethylene glycol via highly selective intermolecular alcohol oxidation, Name: 3,3,3-Trifluoropropan-1-ol, the publication is Green Chemistry (2022), 24(5), 2017-2026, database is CAplus.

One of the ideal green esterification reactions is aerobic oxidative esterification using only a stoichiometric amount of different alcs. via intermol. selective alc. oxidation followed by hemiacetal formation by the addition of the other alc. and hemiacetal oxidation to esters. However, oxalic acid diester synthesis via oxidative esterification has not been reported to date, possibly owing to the difficulty of selectivity control of intermol. alc. oxidation and the chelating effects of ethylene glycol-derived alcs./hemiacetals on inhibiting oxidation catalysts. Herein, using a CuCl/tetramethylethylenediamine/1,5-dimethyl-9-azanoradamantane N-oxyl catalyst, authors describe a highly efficient aerobic oxidative esterification reaction of ethylene glycol to various oxalic acid diesters via selective oxidation of ethylene glycol-derived alcs./hemiacetals even in the presence of other aliphatic primary alcs. Notably, the green reaction works well using an ideal stoichiometric ratio of ethylene glycol and primary/secondary alcs. Thorough exptl. investigation and theor. calculations revealed that highly selective oxidative esterification is enabled by the preferential bidentate coordination of ethylene glycol-derived alcs./hemiacetals to the Cu(II) species, followed by efficient two-electron/one-proton transfer.

Green Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Name: 3,3,3-Trifluoropropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Zhang, Heng published the artcileSynthesis and evaluation of fluorine-substituted phenyl acetate derivatives as ultra-short recovery sedative/hypnotic agents, Product Details of C3H5F3O, the publication is PLoS One (2014), 9(5), e96518/1-e96518/14, 14 pp., database is CAplus and MEDLINE.

Soft drugs are mols. that are purposefully designed to be rapidly metabolized (metabolically labile). In anesthesia, the soft drug is useful because it enables precise titration to effect and rapid recovery, which might allow swift and clear-headed recovery of consciousness and early home readiness. Propofol may cause delayed awakening after prolonged infusion. Propanidid and AZD3043 have a different metabolic pathway compared to propofol, resulting in a short-acting clin. profile. Fluorine imparts a variety of properties to certain medicines, including an enhanced absorption rate and improved drug transport across the blood-brain barrier. The authors hypothesized that the introduction of fluorine to the frame structure of propanidid and AZD3043 would further accelerate the swift and clear-headed recovery of consciousness. To test this hypothesis, we developed a series of fluorine-containing Ph acetate derivatives Fluorine-containing Ph acetate derivatives were synthesized, and their hypnotic potencies and durations of LORR following bolus or infusion administration were determined in mice, rats and rabbits. The metabolic half-lives in the blood of various species were determined chromatog. In vitro radioligand binding and γ-aminobutyric acid A (GABAA) receptor electrophysiol. studies were performed. Among the 12 synthesized fluorine-containing Ph acetate derivatives, compound 5j induced comparable duration of LORR with AZD3043, but more rapid recovery than AZD3043, propanidid and propofol. The time of compound 5j to return to walk and behavioral recovery are approx. reduced by more than 50% compared to AZD3043 in mice and rats and rabbits. The HD50 of compound 5j decreased with increasing animal size. The rapid recovery might make compound 5j suitable for precise titration and allow swift and clear-headed recovery of consciousness and early home readiness.

PLoS One published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C15H21BO2, Product Details of C3H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Yu, Jia-Hui published the artcileSynthetic cajaninstilbene acid derivatives eradicate methicillin-resistant Staphylococcus aureus persisters and biofilms, Quality Control of 2240-88-2, the publication is European Journal of Medicinal Chemistry (2021), 113691, database is CAplus and MEDLINE.

The Staphylococcus aureus can switch to a transient genotype-invariant dormancy, known as a persister, to survive treatment with high doses of antibiotics. This transient persister is an important reason underlying its resistance. There is an urgent need to find new antibacterial agents capable of eradicating methicillin-resistant S. aureus (MRSA) persisters. In this study, 37 new derivatives of cajaninstilbene acid (CSA) were designed and synthesized, and their biol. activity against MRSA persisters was evaluated. Most of the newly synthesized derivatives exhibit more potent antimicrobial properties against S. aureus and MRSA than CSA itself, and 23 of the 37 derivatives show a tendency to eradicate MRSA persisters. A representative compound, I, was demonstrated to target bacterial cell membranes. It eradicated the adherent biofilm of MRSA in a concentration dependent manner, and showed a synergistic antibacterial effect with piperacilin. In a model mouse abscess caused by MRSA persisters, I effectively reduced the bacterial load in vivo. These results indicate that I is a potential candidate for treatment of MRSA persister infections.

European Journal of Medicinal Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C11H15NOS, Quality Control of 2240-88-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gentles, Robert G. published the artcileStandardization Protocols and Optimized Precursor Sets for the Efficient Application of Automated Parallel Synthesis to Lead Optimization: A Mitsunobu Example, Recommanded Product: 3,3,3-Trifluoropropan-1-ol, the publication is Journal of Combinatorial Chemistry (2002), 4(5), 442-456, database is CAplus and MEDLINE.

Mitsunobu reactions of alcs. and phenols to give aryl alkyl ethers are optimized for automated parallel synthesis with potential use in lead optimization for drug discovery. Phenols are first selected to eliminate reactants with mol. weights > 210 g/mol, reactants with other potential reactive moieties which could interfere with biol. activity, labeled mols., reactants which might be incompatible with conditions for the Mitsunobu reaction, and reactants which are not com. available in multigram quantities from major vendors. Once the candidate phenols are selected, reactions of a set of alcs. with a single phenol substrate and reactions of a single alc. substrate with a variety of phenols are studied to compare the manual and automated versions of the Mitsunobu reaction. Both the automated and manual Mitsunobu reactions use di-tert-Bu azodicarboxylate (DBAD) and resin-bound triphenylphosphine as reagents. The resin-bound triphenylphosphine works best when exposure to air is minimized; in addition, use of resin-bound triphenylphosphine with consistent loading is important. With the automated and standardized methodol., a variety of aryl alkyl ethers are prepared

Journal of Combinatorial Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Recommanded Product: 3,3,3-Trifluoropropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Souers, Andrew J. published the artcileSynthesis and evaluation of 2-amino-8-alkoxy quinolines as MCHr1 antagonists. Part 1, Computed Properties of 2240-88-2, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(19), 4873-4877, database is CAplus and MEDLINE.

A high-throughput screen was performed in order to identify compounds that were bound by the melanin concentrating hormone receptor-1. 2-Amino-8-(cyclohexylmethyloxy)quinoline was identified and subsequently optimized using a parallel and automated procedure for the rapid production of multiple analogs. The structure-activity relationships that emerged from this effort are described, along with selected pharmacokinetic parameters of (d)-I when dosed orally in diet-induced obese mice.

Bioorganic & Medicinal Chemistry Letters published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C12H13F2N3O4S, Computed Properties of 2240-88-2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Fontenelle, Clement Q. published the artcileDesign of fluorinated 5-HT₄R antagonists: Influence of the basicity and lipophilicity toward the 5-HT₄R binding affinities, Product Details of C3H5F3O, the publication is Bioorganic & Medicinal Chemistry (2013), 21(23), 7529-7538, database is CAplus and MEDLINE.

Analogs of potent 5-HT₄R antagonists possessing a fluorinated N-alkyl chain have been synthesized to investigate the effect of the resulting change in basicity and lipophilicity on the affinity and selectivity profile. The authors demonstrate that for this series, the affinity is decreased with decreased basicity of the piperidine’s nitrogen atom. In contrast, the resulting increase in lipophilicity has minimal impact on binding affinity and selectivity. 3,3,3-Trifluoropropyl and derivatives 7-Fluoro-5-[1-(4,4,4-triuorobutyl)piperidin-4yl]methyloxybenzo[h]-1,6-naphthyridine 4,4,4-trifluorobutyl and 7-Fluoro-5-[1-(3,3,3-triuoropropyl)piperidin-4yl]methyloxybenzo[h]-1,6-naphthyridine have shown to bind to the 5-HT₄R while maintaining their pharmacol. profile and selectivity toward other 5-HT receptors.

Bioorganic & Medicinal Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Product Details of C3H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Jeffries, Benjamin published the artcileReducing the Lipophilicity of Perfluoroalkyl Groups by CF₂-F/CF₂-Me or CF₃/CH₃ Exchange, Recommanded Product: 3,3,3-Trifluoropropan-1-ol, the publication is Journal of Medicinal Chemistry (2018), 61(23), 10602-10618, database is CAplus and MEDLINE.

Fluorination is commonly employed to optimize bioactivity and pharmaco-kinetic properties of drug candidates. Aliphatic fluorination often reduces the lipophilicity (log P), but polyfluoroalkylation typically increases lipophilicity. Hence, identification of polyfluorinated motifs that nonetheless lead to similar or even reduced lipophilicities is of interest to expand the arsenal of medicinal chem. tools in tackling properties such as compound metabolic stability or off-target selectivity. We show that changing a CF₃-group of a perfluoroalkyl chain to a Me group leads to a drastic reduction in lipophilicity. We also show that changing a C-F bond of a trifluoromethyl group, including when incorporated as part of a perfluoroalkyl group, to a C-Me group, leads to a reduction in log P, despite the resulting chain elongation. The observed lipophilicity trends were identified in fluorinated alkanol models and reproduced when incorporated in analogs of a drug candidate, and the metabolic stability of these motifs was demonstrated.

Journal of Medicinal Chemistry published new progress about 2240-88-2. 2240-88-2 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol, name is 3,3,3-Trifluoropropan-1-ol, and the molecular formula is C3H5F3O, Recommanded Product: 3,3,3-Trifluoropropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts