Tag: M.W=100-150

Sha, Feng published the artcileLigand- and Additive-Controlled Pd-Catalyzed Aminocarbonylation of Alkynes with Aminophenols: Highly Chemo- and Regioselective Synthesis of α,β-Unsaturated Amides, Safety of 3-(Methylamino)phenol, the publication is ACS Catalysis (2017), 7(3), 2220-2229, database is CAplus.

This work describes the chemo- and regioselective direct aminocarbonylation of alkynes withh aminophenols to form hydroxy-substituted α,β-unsaturated amides in good to excellent yields. The latter are valuable compounds in pharmaceuticals and natural products. By a simple choice of different ligands and additives, branched or linear isomers could be selectively formed in excellent regioselectivity. Using a combination of boronic acid and 5-chlorosalicylic acid (“BCSA”) as the additives, linear amides were obtained in high yields and selectivities using 1,2-bis(di-tert-butylphosphinomethyl)benzene (DTBPMB) as the ligand. On the other hand, branched amides could be approached by introducing 1,3-bis(diphenylphosphino)propane as the ligand and p-TsOH·H₂O as the additive. In addition to the hydroxyl group, other functional substituents, such as carboxyl and vinyl groups, could also be tolerated using this method. As an application of this strategy, the natural product avenanthramide A could be synthesized directly in 84% yield and in 99% regioselectivity via the carbonylation of 2-amino-5-hydroxybenzoic acid and 4-ethynylphenol. Further studies show that the ligands and the additives are keys to good yields and selectivities.

ACS Catalysis 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 C11H21BO2Si, Safety of 3-(Methylamino)phenol.

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

Alqarni, Sara A. published the artcileDevelopment of a Fluorescent Nanofibrous Template by In Situ S_NAr Polymerization of Fluorine-Containing Terphenyls with Aliphatic Diols: Self-Assembly and Optical and Liquid Crystal Properties, Category: alcohols-buliding-blocks, the publication is ACS Omega (2021), 6(50), 35030-35038, database is CAplus and MEDLINE.

Stimulus-responsive supramol. organogels have been broadly studied, but the assembly of a liquid crystalline organogel with a thermoreversible response remains a challenge. This could be attributed to the difficulty of designing organogelators with liquid crystalline properties. Nucleophilic aromatic substitution (S_NAr) has been utilized to produce a diversity of pentafluorobenzene-containing aromatics, which are very regioselective to para positions. Those pentafluorobenzene-functionalized aromatics have been ideal compounds for the preparation of calamitic liquid crystals. In this context, novel fluoroterphenyl-containing main-chain polyether (FTP@PE) was synthesized using in situ S_NAr polymerization as a convenient and effective synthetic strategy toward the development of fluorescent liquid crystals bearing fluoroterphenyl and ether groups. The fluoroterphenyl unit was synthesized by Cu(I)-supported decarboxylation cross-coupling of potassium pentafluorobenzoate and 1,4-diiodobenzene. The chem. structures of FTP@PE were studied with ¹H/¹³C/¹⁹F NMR and IR spectra. The liquid crystal mesophases were determined with differential scanning calorimetry and polarizing optical microscopy. UV-visible absorbance and emission spectral profiles showed solvatochromic activity. The nanofibrous morphologies were studied with a scanning electron microscope. The organogels of FTP@PE were developed in a number of solvents via van der Waals attraction forces of aliphatic moieties and π stacking of fluoroterphenyl groups. They demonstrated thermoreversible responsiveness.

ACS Omega published new progress about 111-29-5. 111-29-5 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ploymers, name is Pentane-1,5-diol, and the molecular formula is C5H12O2, Category: alcohols-buliding-blocks.

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

Avery, Mitchell A. published the artcileStructure-Activity Relationships of the Antimalarial Agent Artemisinin. 7. Direct Modification of (+)-Artemisinin and In Vivo Antimalarial Screening of New, Potential Preclinical Antimalarial Candidates, Formula: C3H5F3O, the publication is Journal of Medicinal Chemistry (2002), 45(19), 4321-4335, database is CAplus and MEDLINE.

On the basis of earlier reported quant. structure-activity relationship studies, a series of 9β-16-(arylalkyl)-10-deoxoartemisinins, e.g. I, were proposed for synthesis. Several of the new compounds were synthesized employing the key synthetic intermediate II. In a second approach, the natural product (+)-artemisinic acid (III) was utilized as an acceptor for conjugate addition, and the resultant homologated acids were subjected to singlet oxygenation and acid treatment to provide artemisinin analogs. Under a new approach, we developed a one step reaction for the interconversion of artemisinin into artemisitene (IV) that did not employ selenium-based reagents and found that 2-arylethyliodides would undergo facile radical-induced conjugate addition to the exomethylene lactone of IV in good yield. The lactone carbonyls were removed sequentially by diisobutylaluminum hydride reduction followed directly by a second reduction (BF₃-etherate/Et₃SiH) to afford the desired corresponding pyrans. Six addnl. halogen-substituted aromatic side chains were installed via IV furnishing the bioassay candidates. The analogs were examined for in vitro antimalarial activity in the W-2 and D-6 clones of Plasmodium falciparum and were addnl. tested in vivo in Plasmodium berghei- and/or Plasmodium yoelii-infected mice. Several of the compounds emerged as highly potent orally active candidates without obvious toxicity. Of these, two were chosen for pharmacokinetic evaluation, V and VI.

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, Formula: C3H5F3O.

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

Takechi, Naoto published the artcileNovel Nucleophilic Trifluoromethylation of Vicinal Diol Cyclic Sulfates, Formula: C3H5F3O, the publication is Organic Letters (2002), 4(26), 4671-4672, database is CAplus and MEDLINE.

A novel method for highly regioselective and stereospecific nucleophilic trifluoromethylation of vicinal diol cyclic sulfates, using the reagent derived from reduction of trifluoromethyl iodide by tetrakis(dimethylamino)ethylene (TDAE), is presented.

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 C10H15ClO3S, Formula: C3H5F3O.

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

Nagata, Akiko published the artcileSynthetic chemical probes that dissect vitamin D activities, Safety of 2-Morpholinoethanol, the publication is ACS Chemical Biology (2019), 14(12), 2851-2858, database is CAplus and MEDLINE.

Vitamin D₃ metabolites are capable of controlling gene expression in mammalian cells through two independent pathways: vitamin D receptor (VDR) and sterol regulatory element-binding protein (SREBP) pathways. In the present study, we dissect the complex biol. activity of vitamin D by designing synthetic vitamin D₃ analogs specific for VDR or SREBP pathway, i.e., a VDR activator that lacks SREBP inhibitory activity, or an SREBP inhibitor devoid of VDR activity. These synthetic vitamin D probes permitted identification of one of the vitamin D-responsive genes, Soat1, as an SREBP-suppressed gene. The chem. probes developed in the present study may prove useful in dissecting the intricate interplay of vitamin D actions, thereby providing insights into how vitamin D target genes are regulated.

ACS Chemical Biology 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, Safety of 2-Morpholinoethanol.

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

Kojima, Ryoto published the artcileA Copper(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl-Substituted Alkenes: Synthesis of Enantioenriched γ,γ-gem-Difluoroallylboronates, Synthetic Route of 83706-94-9, the publication is Angewandte Chemie, International Edition (2018), 57(24), 7196-7199, database is CAplus and MEDLINE.

The first catalytic enantioselective γ-boryl substitution of CF₃-substituted alkenes is reported. A series of CF₃-substituted alkenes was treated with a diboron reagent in the presence of a copper(I)/Josiphos catalyst to afford the corresponding optically active γ,γ-gem-difluoroallylboronates in high enantioselectivity. The thus obtained products could be readily converted into the corresponding difluoromethylene-containing homoallylic alcs. using highly stereospecific allylation reactions.

Angewandte Chemie, International Edition published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Synthetic Route of 83706-94-9.

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

Samav, Yasemin published the artcilePreparation of Responsive Zwitterionic Diblock Copolymers Containing Phosphate and Phosphonate Groups, Application In Synthesis of 622-40-2, the publication is Macromolecular Research (2020), 28(12), 1134-1141, database is CAplus.

In this study, novel zwitterionic diblock copolymers, namely poly(2-(N-morpholino)ethyl methacrylate)-block-poly(2-(methacryloyloxy)ethyl phosphate) (PMEMA-b-PMOEP) and poly-2-(N-morpholino)ethyl methacrylate-block-poly ((methacryloyloxy)methyl phosphonic acid) (PMEMA-b-PMOMP), were synthesized via reversible addition-fragmentation chain transfer controlled radical polymerization Solution properties of these phosphorus-based diblock copolymers were investigated using dynamic light scattering, transmission electron microscopy and proton NMR spectroscopy. Since the PMEMA block has both salt- and thermo-responsive properties, PMEMA-b-PMOEP and PMEMA-b-PMOMP diblock copolymers formed core-shell micelles in basic aqueous media as the PMEMA block formed insoluble micelle core with the addition of Na₂SO₄ or an increase in temperature in basic solution Addnl., PMEMA-b-PMOMP diblock copolymers interacted strongly with calcium cations and yielded reverse micellar structures via complexation of phosphate with metal cation in aqueous media.

Macromolecular Research 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

Mazari, Shaukat Ali published the artcileThermal degradation kinetics of morpholine for carbon dioxide capture, Recommanded Product: 2-Morpholinoethanol, the publication is Journal of Environmental Chemical Engineering (2020), 8(3), 103814, database is CAplus.

Deterioration of amines under process operating conditions for sour gas treatment is a severe problem. New amines are being investigated to replace conventional amines which face operational, economic and environmental challenges. Morpholine (MOR) is an understudied amine for carbon dioxide (CO₂) capture which comes with good CO₂ capture characteristics like CO₂ absorption rate, CO₂ solubility etc. This study investigates the stability of aqueous morpholine under stripper conditions. Effect of CO₂ loading and temperature have been investigated on the degradation kinetics of MOR. CO₂ loading is varied from 0 to 0.48 mol CO₂/mol alkalinity and temperatures is varied 135-190°C. Thermal degradation experiments were conducted using 316 stainless steel cylinders, closed with Swagelok endcaps. The degraded samples were analyzed by using Gas Chromatog.-Mass Spectrometry (GC-MS), Gas Chromatog.-Flame Ionization Detector (GC-FID) and Liquid Chromatog. Quadrupole Time-of-Flight Mass Spectrometry (LC-QToF-MS) for morpholine concentration and identification of degradation products. Morpholine demonstrated higher stability up to 150°C. However, higher degradation rate is found at temperatures 175°C and above. Degradation rate increases with CO₂ loading. Identified degradation products are tabulated in the text and reaction mechanisms for formation of some of the key degradation products are also provided. A kinetic model for the rate of degradation of morpholine is proposed, which shows a decent agreement with exptl. data. Comparison shows that morpholine is thermally more stable compared to monoethanolamine (MEA), diethanolamine (DEA), methyldiethanolamine (MDEA) and piperazine (PZ).

Journal of Environmental Chemical Engineering 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, Recommanded Product: 2-Morpholinoethanol.

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

Abraham, Michael H. published the artcileDescriptors for fluorotelomere alcohols. Calculation of physicochemical properties, Application of 3,3,3-Trifluoropropan-1-ol, the publication is Physics and Chemistry of Liquids (2021), 59(6), 932-937, database is CAplus.

Abraham model solute descriptors are calculated for several environmentally important fluorotelomer alcs. from published partition coefficient and solubility data. The various descriptors all show a gradual trend from 1:2FTOH to 8:2FTOH. The maximum deviation from self-consistent values is 0.19 log units in the calculations on vapor pressure (concentration in air) and solubility in water (concentration in water).

Physics and Chemistry of Liquids 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

Simoes, Ana V. C. published the artcileAmphiphilic meso(sulfonate ester fluoroaryl)porphyrins: refining the substituents of porphyrin derivatives for phototherapy and diagnostics, Quality Control of 2240-88-2, the publication is Tetrahedron (2012), 68(42), 8767-8772, database is CAplus.

A set of amphiphilic fluorinated porphyrins appended with sulfonate ester groups were synthesized and fully characterized. The reaction proceeds efficiently, with high yields, with an improved methodol. Their potential use as imaging and phototherapeutic agents was assessed measuring relevant photophys. properties. It is shown that these porphyrins have good photostability, long triplet lifetimes (between 47 μs and 102 μs), high singlet oxygen quantum yields (0.74≤FD≤1.00), low fluorescence quantum yields (<0.04) and sharp ¹⁹F NMR peaks. The data on the new meso(sulfonate ester fluoroaryl)porphyrins illustrate the potential of perfluorinated sulfonate esters to improve phys. properties relevant for cancer imaging and photodynamic therapy.

Tetrahedron 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 C10H16Br3N, Quality Control of 2240-88-2.

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