Category: 2240-88-2

Linclau, Bruno published the artcileInvestigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method, Recommanded Product: 3,3,3-Trifluoropropan-1-ol, the publication is Angewandte Chemie, International Edition (2016), 55(2), 674-678, database is CAplus and MEDLINE.

Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds An important application is lipophilicity (log P) modulation. However, the determination of log P is cumbersome for non-UV-active compounds A new variation of the shake-flask log P determination method is presented, enabling the measurement of log P for fluorinated compounds with or without UV activity regardless of whether they are hydrophilic or lipophilic. No calibration curves or measurements of compound masses/aliquot volumes are required. With this method, the influence of fluorination on the lipophilicity of fluorinated aliphatic alcs. was determined, and the log P values of fluorinated carbohydrates were measured. Interesting trends and changes, for example, for the dependence on relative stereochem., are reported.

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, Recommanded Product: 3,3,3-Trifluoropropan-1-ol.

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

Zhang, Yong-Kang published the artcileBenzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate, COA of Formula: C3H5F3O, the publication is Journal of Medicinal Chemistry (2017), 60(13), 5889-5908, database is CAplus and MEDLINE.

Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a mol. with satisfactory antimalarial activity, physicochem. properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclin. development.

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 C18H34N4O5S, COA of Formula: C3H5F3O.

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

Linclau, Bruno published the artcileIntramolecular OH…Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif, Formula: C3H5F3O, the publication is Chemistry – A European Journal (2015), 21(49), 17808-17816, database is CAplus and MEDLINE.

Fluorination is commonly exercised in compound property optimization. However, the influence of fluorination on hydrogen-bond (HB) properties of adjacent functional groups, as well as the HB-accepting capacity of fluorine itself, is still not completely understood. Although the formation of OH…F intramol. HBs (IMHBs) was established for conformationally restricted fluorohydrins, such interaction in flexible compounds remained questionable. Herein is demonstrated for the first time-and in contrast to earlier reports-the occurrence of OH…F IMHBs in acyclic saturated γ-fluorohydrins, even for the parent 3-fluoropropan-1-ol. The relative stereochem. has a crucial influence on the corresponding ^h1J(OH…F) values, as illustrated by syn- and anti-4-fluoropentan-2-ol (6.6 and 1.9 Hz). The magnitude of OH…F IMHBs and their strong dependence on the overall mol. conformational profile, fluorination motif, and alkyl substitution level, is rationalized by quantum chem. calculations For a given alkyl chain, the rule of shielding applies to OH…F IMHB energies. Surprisingly, the predicted OH…F IMHB energies are only moderately weaker than these of the corresponding OH…OMe. These results provide new insights of the impact of fluorination of aliphatic alcs., with attractive perspectives for rational drug design.

Chemistry – A European Journal 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

Empel, Claire published the artcileProton or Carbene Transfer? On the Dark and Light Reaction of Diazoalkanes with Alcohols, HPLC of Formula: 2240-88-2, the publication is Chemistry – A European Journal (2022), 28(15), e202104397, database is CAplus and MEDLINE.

A fundamental understanding of the reaction of diazoalkanes with alcs. to made this transformation amenable to a generalized approach towards formal alkylation reactions of alcs. with diazoalkanes was aimed. Exptl. and theor. studies suggested a direct proton transfer only in exceptional cases. In a more general setting, such O-H functionalization proceeded both under dark and photochem. conditions via a key hydrogen-bonded singlet carbene intermediate that underwent a protonation-addition mechanism. Applications of this approach in O-H functionalization reactions of alcs., including simple fluorinated, halogenated and aliphatic alcs. and showcase functional-group tolerance of this method in the reaction of biol. active and pharmaceutically relevant alcs. was concluded.

Chemistry – A European Journal 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, HPLC of Formula: 2240-88-2.

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

Papadimitriou, Vassileios C. published the artcileKinetic Study of the Reactions of Cl Atoms with CF₃CH₂CH₂OH, CF₃CF₂CH₂OH, CHF₂CF₂CH₂OH, and CF₃CHFCF₂CH₂OH, Computed Properties of 2240-88-2, the publication is Journal of Physical Chemistry A (2007), 111(45), 11608-11617, database is CAplus and MEDLINE.

The reaction kinetics of chlorine atoms with a series of partially fluorinated straight-chain alcs., CF₃CH₂CH₂OH (1), CF₃CF₂CH₂OH (2), CHF₂CF₂CH₂OH (3), and CF₃CHFCF₂CH₂OH (4), were studied in the gas phase over the temperature range of 273-363 K by using very low-pressure reactor mass spectrometry. The absolute rate coefficients were given by the expressions (in cm³ mol.^-1 s^-1): k₁ = (4.42 ± 0.48) × 10^-11 exp(-255 ± 20/T); k₁(303) = (1.90 ± 0.17) × 10^-11, k₂ = (2.23 ± 0.31) × 10^-11 exp(-1065 ± 106/ T); k₂(303) = (6.78 ± 0.63) × 10^-13, k₃ = (8.51 ± 0.62) × 10^-12 exp(-681 ± 72/T); k₃(303) = (9.00 ± 0.82) × 10^-13 and k₄ = (6.18 ± 0.84) × 10^-12 exp(-736 ± 42/T); k₄(303) = (5.36 ± 0.51) × 10^-13. The quoted 2σ uncertainties include the systematic errors. All title reactions proceed via a hydrogen atom metathesis mechanism leading to HCl. Moreover, the oxidation of the primarily produced radicals was investigated, and the end products were the corresponding aldehydes (R_F-CHO; R_F = -CH₂CF₃, -CF₂CF₃, -CF₂CHF₂, and -CF₂CHFCF₃), providing a strong exptl. indication that the primary reactions proceed mainly via the abstraction of a methylenic hydrogen adjacent to a hydroxyl group. Finally, the bond strengths and ionization potentials for the title compounds were determined by d. functional theory calculations, which also suggest that the α-methylenic hydrogen is mainly under abstraction by Cl atoms. The correlation of room-temperature rate coefficients with ionization potentials for a set of 27 mols., comprising fluorinated C2-C5 ethers and C2-C4 alcs., is good with an average deviation of a factor of 2, and is given by the expression log(k) (in cm³ mol.^-1 s^-1) = (5.8 ± 1.4) – (1.56 ± 0.13) × (ionization potential (in eV)).

Journal of Physical Chemistry A 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, Computed Properties of 2240-88-2.

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

Ferguson published the artcileCharacterization of the Unimolecular Water Elimination Reaction from 1-Propanol, 3,3,3-Propan-1-ol-d₃, 3,3,3-Trifluoropropan-1-ol, and 3-Chloropropan-1-ol, Name: 3,3,3-Trifluoropropan-1-ol, the publication is Journal of Physical Chemistry A (2009), 113(37), 10013-10023, database is CAplus and MEDLINE.

The unimol. reactions of 1-propanol, 3,3,3-propan-1-ol-d₃, 3,3,3-trifluoropropan-1-ol, and 3-chloropropan-1-ol have been studied by the chem. activation technique. The recombination of CH₃, CD₃, CF₃, and CH₂Cl radicals with CH₂CH₂OH radicals at room temperature was used to generate vibrationally excited CH₃CH₂CH₂OH, CD₃CH₂CH₂OH, CF₃CH₂CH₂OH, and CH₂ClCH₂CH₂OH mols. The principal unimol. reaction for propanol and propanol-d₃ with 90 kcal mol^-1 of vibrational energy is 1,2-H₂O elimination with rate constants of 3.4 × 10⁵ and 1.4 × 10⁵ s^-1, resp. For CH₂ClCH₂CH₂OH also with 90 kcal mol^-1 of energy, 2,3-HCl elimination with a rate constant of 3.0 × 10⁷ s^-1 is more important than 1,2-H₂O elimination; the branching fractions are 0.95 and 0.05. For CF₃CH₂CH₂OH with an energy of 102 kcal mol^-1, 1,2-H₂O elimination has a rate constant of 7.9 × 10⁵ and 2,3-HF elimination has a rate constant of 2.6 × 10⁵ s^-1. D. functional theory was used to obtain models for the mols. and their transition states. The frequencies and moments of inertia from these models were used to calculate RRKM rate constants, which were used to assign threshold energies by comparing calculated and exptl. rate constants This comparison gives the threshold energy for H₂O elimination from 1-propanol as 64 kcal mol^-1. The threshold energies for 1,2-H₂O and 2,3-HCl elimination from CH₂ClCH₂CH₂OH were 59 and 54 kcal mol^-1, resp. The threshold energies for H₂O and HF elimination from CF₃CH₂CH₂OH are 62 and 70 kcal mol^-1, resp. The structures of the transition states for elimination of HF, HCl, and H₂O are compared.

Journal of Physical Chemistry A 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

Heger, Matthias published the artcileBracketing subtle conformational energy differences between self-solvated and stretched trifluoropropanol, Application of 3,3,3-Trifluoropropan-1-ol, the publication is Physical Chemistry Chemical Physics (2015), 17(15), 9899-9909, database is CAplus and MEDLINE.

The intramol. OH···F hydrogen bond in 3,3,3-trifluoropropanol (TFP) exerts a subtle stabilizing effect that, when compared to the non-fluorinated analog, reorders the five distinguishable conformers and widens the gap between the two most stable structures. Here, we combine findings from Raman spectroscopy in supersonic expansions and high-level quantum-chem. calculations to bracket the energy difference between the two most stable TFP structures at 1.7(5) kJ mol^-1. The torsional potential energy surface suggests consecutive backbone and OH torsional motions for the conformer interconversion, which are discussed in the framework of supersonic jet cooling as a function of nozzle temperature The picture of a bistable cold mol. with trans or gauche backbone emerges, in which the OH group controls the energy difference and modulates the high barrier separating the heavy atom frames.

Physical Chemistry Chemical Physics 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, Application of 3,3,3-Trifluoropropan-1-ol.

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

Bonnet, Nelly published the artcileIonic strength mediated hydrophobic force switching of CF₃-terminated ethylene glycol self-assembled monolayers (SAMs) on gold, Quality Control of 2240-88-2, the publication is Chemical Communications (Cambridge, United Kingdom) (2007), 5066-5068, database is CAplus and MEDLINE.

We have synthesized oligo(ethylene glycol) CF₃-terminated switching self-assembled monolayers, which allow the force experienced by a hydrophobic object to be controlled via the ionic strength of the environment.

Chemical Communications (Cambridge, United Kingdom) 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, Quality Control of 2240-88-2.

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

Ochiai, Hiroshi published the artcileOrally active PDE4 inhibitor with therapeutic potential, Application of 3,3,3-Trifluoropropan-1-ol, the publication is European Journal of Medicinal Chemistry (2004), 39(7), 555-571, database is CAplus and MEDLINE.

Based on the promising results obtained by the clin. trial of Ariflo (I), further optimization of the spatial arrangement of the three pharmacophores (the carboxylic acid moiety, nitrile moiety and 3-cyclopentyloxy-4-methoxyphenyl moiety) in the structure of I was attempted using a bicyclo[3 3 0]octane template with more stereochem. diversity than the cyclohexane template of I. Biol. evaluation of the decyanated analogs and further optimization of the cyclopentyloxy moiety of II (R = cyclopentyl; X = OH, NHOH) were also performed. Among the compounds tested, II [R = cyclopentyl; X = OH (III)], IV and II (X = OH, R = 2,3-dihydro-1H-indene-2-yl) were found to be orally active and were estimated to have therapeutic potential based on cross-species and same-species comparisons. The structure-activity relationships (SARs) of these compounds were investigated and pharmacokinetic data for III and IV (X = NHOH) were also obtained by single-dose studies in rats.

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 C3H5F3O, Application of 3,3,3-Trifluoropropan-1-ol.

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

Drouet, Fleur published the artcileA Convenient Method for the Asymmetric Synthesis of Fluorinated α-Amino Acids from Alcohols, Synthetic Route of 2240-88-2, the publication is European Journal of Organic Chemistry (2014), 2014(6), 1195-1201, database is CAplus.

Due to their numerous applications, fluorinated amino acids have recently attracted significant attention. The preparation of fluorine-containing phenylalanines and aliphatic fluorinated amino acids using Mitsunobu-Tsunoda alkylation of a chiral nucleophilic glycine equivalent with readily available alc. substrates is described. The reaction proceeds in high yields and with excellent diastereoselectivity. This method provides an efficient synthetic route to fluorinated amino acids for which asym. approaches are scarce.

European Journal of Organic 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, Synthetic Route of 2240-88-2.

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