Tag: M.W=100-150

Wentworth, Anita D. published the artcileA Soluble Polymer-Supported Triflating Reagent: A High-Throughput Synthetic Approach to Aryl and Enol Triflates, Formula: C4H4OS, the publication is Organic Letters (2000), 2(4), 477-480, database is CAplus and MEDLINE.

The high-yielding synthesis and application of the first example of a polymer-supported reagent for the preparation of trifluoromethanesulfonates (triflates), 4-(F₃CSO₂)₂NC₆H₄(OCH₂CH₂)_nOC₆H₄N(SO₂CF₃)₂, is described. This new reagent efficiently triflates aryl alcs. and lithium enolates in high yield (>90%). A simple precipitation and filtration to remove the excess reagent and byproduct facilitate purification of the triflate products. The PEG-supported approach is highly efficient, as the PEG-supported byproduct can be quant. recovered and recycled into reagent.

Organic Letters published new progress about 17236-59-8. 17236-59-8 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Alcohol, name is Thiophen-3-ol, and the molecular formula is C7H8BFO2, Formula: C4H4OS.

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

Singh, Rajeeva published the artcileComparisons of rate constants for thiolate-disulfide interchange in water and in polar aprotic solvents using dynamic proton NMR line shape analysis, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (1990), 112(3), 1190-7, database is CAplus.

The rate constants for representative thiolate-disulfide interchange reactions are larger in DMSO and DMF than in water by a factor of ∼2300 at 24°. The log of the rate constant is directly proportional to the mole fraction of D₂O in mixtures of DMSO and D₂O, even at small mole fractions of D₂O. This linear proportionality suggests that thiolate anion is not specifically solvated by water and that hydrogen bonding is relatively unimportant in stabilizing this species. The values of ΔS^⧧ for thiolate-disulfide interchange are ∼-10 cal/(deg mol), presumptively because of loss in the entropy of the reactants in going from ground to transition state, partially compensated by a gain in entropy from solvent release. Introduction of a hydroxy group β to the C-S bond slows the reaction by a factor of 2-15; the introduction of Me groups β to the C-S bond slows the rate by factors of 3-20.

Journal of the American Chemical Society published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C23H20BN, Category: alcohols-buliding-blocks.

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

Liu, Ye published the artcileInfluence of the Electronic Properties of the Ligand on the Photoelectrochemical Behavior of Au₂₅ Nanocluster-Sensitized TiO₂ Photoanode, Category: alcohols-buliding-blocks, the publication is Journal of Physical Chemistry C (2022), 126(4), 1778-1784, database is CAplus.

Atomically precise metal nanoclusters (NCs) have recently emerged as a new class of bifunctional (photoactive and catalytically active) photosensitizers in light energy conversion applications. Despite the size and alloy effects of NCs, no effort has been made to elucidate how the protecting ligand affects the photoelectrochem. of the NC-sensitized photoelectrodes. With a nanoporous TiO₂ array as model support, Au₂₅ NCs protected by various thiol-bearing ligands have been used to prepare four different photoanodes. It is revealed that a subtle change of the ligand from an alkanethiol to an aromatic thiol facilitates the charge transfer between the NC and TiO₂, which in turn improves the photoelectrochem. performance of the corresponding photoanode by at least 6 times. This new insight highlights the importance of the electronic properties of the ligand on the design of more efficient NC-sensitized photoelectrodes.

Journal of Physical Chemistry C published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Category: alcohols-buliding-blocks.

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

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

Li, Zhang published the artcileDesign, synthesis and evaluation of novel diaryl-1,5-diazoles derivatives bearing morpholine as potent dual COX-2/5-LOX inhibitors and antitumor agents, Application In Synthesis of 622-40-2, the publication is European Journal of Medicinal Chemistry (2019), 168-184, database is CAplus and MEDLINE.

In this paper, 41 hybrid compounds containing diaryl-1,5-diazole and morpholine structures, compounds I [R¹ = H, F, Me, etc.; R² = H, F, Cl, etc.; X = O, S] and II [R³ = H, F, MeO, etc.; Y = O, NH; n = 2,3] acting as dual COX-2/5-LOX inhibitors have been designed, synthesized and biol. evaluated. Most of them showed potent antiproliferative activities and COX-2/5-LOX inhibitory in-vitro. Among them, compound II [R³ = CF₃, Y = NH, n = 3] displayed the most potency against cancer cell lines (IC₅₀ = 6.43-10.97 μM for F10, HeLa, A549 and MCF-7 cells), lower toxicity to non-cancer cells than celecoxib (A33: IC₅₀ = 194.01 μM vs.celecoxib: IC₅₀ = 97.87 μM for 293T cells), and excellent inhibitory activities on COX-2 (IC50 = 0.17 μM) and 5-LOX (IC₅₀ = 0.68 μM). Meanwhile, the mol. modeling study was performed to position compound II [R³ = CF₃, Y = NH, n = 3] into COX-2 and 5-LOX active sites to determine the probable binding models. Mechanistic studies demonstrated that compound II [R³ = CF₃, Y = NH, n = 3] could block cell cycle in G2 phase and subsequently induced apoptosis of F10 cells. Furthermore, compound II [R³ = CF₃, Y = NH, n = 3] could significantly inhibit tumor growth in F10-xenograft mouse model, and pharmacokinetic study of compound A33 indicated that it showed better stability in vivo. In general, compound II [R³ = CF₃, Y = NH, n = 3] could be a promising candidate for cancer therapy.

European Journal of Medicinal Chemistry published new progress about 622-40-2. 622-40-2 belongs to alcohols-buliding-blocks, auxiliary class Morpholine,Alcohol, name is 2-Morpholinoethanol, and the molecular formula is C6H13NO2, Application In Synthesis of 622-40-2.

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

Rybicka-Jasinska, Katarzyna published the artcilePorphyrins as Promising Photocatalysts for Red-Light-Induced Functionalizations of Biomolecules, Recommanded Product: 2-Phenylethanethiol, the publication is ACS Organic & Inorganic Au, database is CAplus.

Red-light enables deeper material penetration, which is important for biol. applications and has consequences for chem. synthesis. Therefore, the search for new photocatalysts that absorb in this region is crucial. Despite the undeniable utility of porphyrins in blue- and green-light-induced energy- and electron-transfer processes, they are also perfectly suited for red-light applications. Herein, we describe free-base porphyrins as photoredox catalysts for red-light-induced organic transformations. They can act as both photooxidants and photoreductants and can accomplish the synthesis of biaryls once merged with Pd-catalysis. The developed methodol. holds promise for broader applications, as the heme-based protoporphyrin is used as a photocatalyst and reactions can be realized in aqueous conditions.

ACS Organic & Inorganic Au published new progress about 4410-99-5. 4410-99-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Benzene, name is 2-Phenylethanethiol, and the molecular formula is C8H10S, Recommanded Product: 2-Phenylethanethiol.

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

Shenghur, Abraham published the artcileTheoretical Study of the Hydrogen Abstraction of Substituted Phenols by Nitrogen Dioxide as a Source of HONO, Application of 3-(Methylamino)phenol, the publication is Journal of Physical Chemistry A (2014), 118(46), 11002-11014, database is CAplus and MEDLINE.

The mild yet promiscuous reactions of nitrogen dioxide (NO₂) and phenolic derivatives to produce nitrous acid (HONO) have been explored with d. functional theory calculations The reaction is found to occur via four distinct pathways with both proton coupled electron transfer (PCET) and hydrogen atom transfer (HAT) mechanisms available. While the parent reaction with phenol may not be significant in the gas phase, electron donating groups in the ortho and para positions facilitate the reduction of nitrogen dioxide by electronically stabilizing the product phenoxy radical. Hydrogen bonding groups in the ortho position may addnl. stabilize the nascent resonantly stabilized radical product, thus enhancing the reaction. Catechol (ortho-hydroxy phenol) has a predicted overall free energy change ΔG⁰ = -0.8 kcal mol^-1 and electronic activation energy E_a = 7.0 kcal mol^-1. Free amines at the ortho and para positions have ΔG⁰ = -3.8 and -1.5 kcal mol^-1; E_a = 2.3 and 2.1 kcal mol^-1, resp. The results indicate that the hydrogen abstraction reactions of these substituted phenols by NO₂ are fast and spontaneous. Hammett constants produce a linear correlation with bond dissociation energy (BDE) demonstrating that the BDE is the main parameter controlling the dark abstraction reaction. The implications for atm. chem. and ground-level nitrous acid production are discussed.

Journal of Physical Chemistry A published new progress about 14703-69-6. 14703-69-6 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Phenol, name is 3-(Methylamino)phenol, and the molecular formula is C9H10N2O, Application of 3-(Methylamino)phenol.

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

Hsin, Ling-Wei published the artcileSynthesis and biological activity of fluoro-substituted pyrrolo[2,3-d]pyrimidines: the development of potential positron emission tomography imaging agents for the corticotropin-releasing hormone type 1 receptor, COA of Formula: C8H19NO, the publication is Bioorganic & Medicinal Chemistry Letters (2000), 10(8), 707-710, database is CAplus and MEDLINE.

A series of fluoro-substituted 4-(dialkylamino)pyrrolo[2,3-d]pyrimidines was synthesized and their binding affinity for corticotropin-releasing hormone type 1 receptor (CRHR₁) was investigated. Thus, N-ethyl-N-(4-fluorobutyl)-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine and N-(4-fluorobutyl)-2,5,6-trimethyl-N-propyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine possessed very high CRHR₁ affinity (K_i=3.5, 0.91 nM, resp.). They are promising candidates for the development of ¹⁸F-containing non-peptide PET radioligands for CRHR₁.

Bioorganic & Medicinal Chemistry Letters published new progress about 4543-95-7. 4543-95-7 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 4-(Butylamino)butan-1-ol, and the molecular formula is C8H19NO, COA of Formula: C8H19NO.

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