Author: tianli

Wollenburg, Marco published the artcileTrans-Selective and Switchable Arene Hydrogenation of Phenol Derivatives, COA of Formula: C13H19Br2ClN2O, the publication is ACS Catalysis (2020), 10(19), 11365-11370, database is CAplus and MEDLINE.

A trans-selective arene hydrogenation of abundant phenol derivatives catalyzed by a com. available heterogeneous palladium catalyst was reported. The described method tolerates a variety of functional groups and provides access to a broad scope of trans-configurated cyclohexanols as potential building blocks for life sciences and beyond in a one-step procedure. The transformation is strategically important because arene hydrogenation preferentially delivers the opposite cis-isomers. The diastereoselectivity of the phenol hydrogenation can be switched to the cis-isomers by employing rhodium-based catalysts. Moreover, a protocol for the chemoselective hydrogenation of phenols to cyclohexanones was developed.

ACS Catalysis published new progress about 23828-92-4. 23828-92-4 belongs to alcohols-buliding-blocks, auxiliary class Membrane Transporter/Ion Channel,Sodium Channel, name is trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride, and the molecular formula is C12H10N2O5, COA of Formula: C13H19Br2ClN2O.

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

Andersen, Sofie Meng published the artcile3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry, Computed Properties of 20880-92-6, the publication is Organic Letters (2015), 17(4), 944-947, database is CAplus and MEDLINE.

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatog. purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

Organic Letters published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Computed Properties of 20880-92-6.

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

Sedlacko, Erin M. published the artcileMetabolomics reveals primary response of wheat (Triticum aestivum) to irrigation with oilfield produced water, Recommanded Product: (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, the publication is Environmental Research, database is CAplus and MEDLINE.

The reuse of oilfield produced water (PW) for agricultural irrigation has received increased attention for utility in drought-stricken regions. It was recently demonstrated that PW irrigation can affect physiol. processes in food crops. However, metabolomic evaluations are important to further discern specific mechanisms of how PW may contribute as a plant-environmental stressor. Herein, the primary metabolic responses of wheat irrigated with PW and matching salinity controls were investigated. Non-targeted gas chromatog. mass spectrometry (GC-MS) metabolomics was combined with multivariate anal. and revealed that PW irrigation altered the primary metabolic profiles of both wheat leaf and grain. Over 600 compounds (183 annotated metabolites) were detected that varied between controls (salinity control and tap water) and PW irrigated plants. While some of these changed metabolites are related to salinity stress, over half were found to be unique to PW. The primary metabolites exhibiting changes in abundance in leaf and grain tissues were amines/amino acids, organic acids, and saccharides. Metabolite pathway anal. revealed that amino acid metabolism, sugar metabolism, and nitrogen remobilization are all impacted by PW irrigation, independent of regular plant responses to salinity stress. These data, when combined with prior physiol. studies, support a multi-faceted, physio-metabolic response of wheat to the unique stressor imposed by irrigation with PW.

Environmental Research published new progress about 526-98-7. 526-98-7 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Other Sugar Units, name is (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid, and the molecular formula is C11H22N2O4, Recommanded Product: (3S,4R,5S)-3,4,5,6-Tetrahydroxy-2-oxohexanoic acid.

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

Corey, E. J. published the artcileA study of the formation of halo amines and cyclic amines by the free radical chain decomposition of N-haloammonium ions (Hofmann-Löffler reaction), Recommanded Product: 4-(Butylamino)butan-1-ol, the publication is Journal of the American Chemical Society (1960), 1657-68, database is CAplus.

cf. Wawzonek and Thelen, CA 44, 9444g; W., et al., CA 46, 2058a. Cyclization of N-halo amines to pyrrolidines by heating in H₂SO₄ was a free-radical chain reaction which was initiated by ultraviolet light or by persulfate and (or) ferrous ions and was inhibited by O. The reaction was acid-catalyzed; the acid most likely accelerated chain-propagation or retarded chain-termination. Five-membered rings were formed almost exclusively. The ease of removal of H from the δ-C involved was tertiary > secondary > primary; there was virtually no competition when different types were present. No pyrrolidines were obtained when the δ-H was tertiary; solvolysis of the intermediate δ-Cl amine apparently predominated. Irradiation of dibutylchloramine in H₂SO₄ did not liberate Cl ion, indicating that a δ-Cl amine was an intermediate. The exptl. data support the Wawzonek mechanism (loc. cit.). For isotope effect and stereochem. studies, some deuteriated amines were synthesized. Valerolactone [66.2% L-(-)isomer, 33.8% D(+)-isomer] (26 g.) and liquid MeNH₂ under N for 7 days in a sealed tube gave 100% crude N-methyl-4-hydroxyvaleramide (I), which with LiAlH₄ gave 39% N-methyl-4-hydroxyamylamine (II), b₈ 97-8°, n²⁵_D 1.4460, [α]²²_D 4.23° (c 10, EtOH). II and p-MeC₆H₄SO₂Cl in pyridine gave 82% (-)-N-methyl-N-(4-p-toluenesulfonoxyamyl)-p-toluenesulfonamide (III), [α]²⁰_D -2.73° (c 10, CHCl₃). Reduction of III with LiAlD₄ gave 73% (-)-methylamylamine-4-d (IV), n²⁵_D 1.4068, α²⁰_D -0.135 ± 0.03° (1 dm.). Cyclization of IV (Coleman, et al., Organic Syntheses Collective volume III, 159(1955)) gave 43% optically inactive 1,2-dimethylpyrrolidine; analysis of the picrate showed 4.88 atom-% D, corresponding to an isotope effect (k_H/k_D) of 3.54 ± 0.5. As a check on the anal. data, 1,2-dimethylpyrrolidine-2-d (V) was synthesized and the isotope effect determined from infrared absorption. 1,2-Dimethyl-2-pyrroline (30 g.), neutralized with 3N HCl and treated with aqueous KCN gave 79% 1,2-dimethyl-2-cyanopyrrolidine (VI), b₃₆ 83-4°, n^22.5_D 1.4447; picrate m. 154.5-6.5° (C₆H₆EtOH). Reduction of VI with LiAlD₄ gave 72% V, b. 94-5°, n²⁵_D 1.4203. From the absorption band at 2040 cm.^-1, the amount of V present in the product from cyclization of IV was determined, giving an isotope effect of 3.42 ± 0.5. N-Butyl-2-pyrrolidone was hydrolyzed with Ba(OH)₂ to 4-butylaminobutyric acid, m. 145-6° (MeOH-Et₂O), which on reduction with LiAlD₄ gave 36% 4-butylaminobutanol-1,1-d₂ (VII), b₁₆ 131-2°, n^24.5_D 1.4508. VII was converted to N-butyl-N-(4-p-toluenesulfonoxybutyl)-p-toluenesulfonamide-4,4-d₂ (oil), which on reduction with LiAlD₄ gave 66% dibutylamine-4,4-d₃ (VIII), b₄₆ 76-7°; HCl salt m. 292-6° (decomposition). Cyclization of VIII after chlorination gave N-butylpyrrolidine, b₅₅ 75°; the infrared absorption showed bands corresponding to N-CD₂– and C-CD₃ groups. The isotope effect for this cyclization, calculated from infrared absorption, was approx. 2.6. Other amine derivatives synthesized for study were as follows. Isocaproyl chloride and amylamine gave 78% N-amylisocaproamide, b_0.35 103-5°, n²²_D 1.4481, which on reduction with LiAlH₄ gave amylisohexylamine, b₁₆ 99-102°, n²²_D 1.4295, yield 81%; HBr salt m. 291-2.5° (decomposition) (dioxane-EtOH). Attempted cyclization of the N-Cl derivative gave no tertiary amines. Similar failure was experienced with butyl-sohexylamine, although HCl was evolved during heating. The product amounted to 0.147 g., b₁₄ about 75°, n^21.8_D 1.4378; HBr salt (IX) m. 162-4° (dioxane). IX was not identical with N-butyl-2,2-dimethylpyrrolidine-HBr nor with N-isohexylpyrrolidine-HBr, which was prepared for comparison by LiAlH₄ reduction of N-isocaproylpyrrolidine [N-isohexylpyrrolidine b₁₅ 79-82°, n²⁵_D 1.4428; HBr salt m. 179-80° (dioxane)].

Journal of the American Chemical Society 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, Recommanded Product: 4-(Butylamino)butan-1-ol.

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

Noyola, Martha published the artcileSynthesis and smooth muscle relaxing activity of a series of 1,4-dihydropyridine nicardipine analogs, Recommanded Product: 2-(Benzyl(methyl)amino)ethanol, the publication is Revista de la Sociedad Quimica de Mexico (2003), 47(1), 34-37, database is CAplus.

Nicardipine (I; R = NO₂) and five new analogs I (R = Cl, Br, F, Me, OMe) were synthesized and evaluated for their smooth muscle relaxing activity. All the compounds displayed significant relaxant activity and I (R = Br) was the most potent; the order of potency for the complete set of derivatives were: Br > NO₂ (nicardipine) > Cl ≈ F > Me ≈ OMe.

Revista de la Sociedad Quimica de Mexico published new progress about 101-98-4. 101-98-4 belongs to alcohols-buliding-blocks, auxiliary class Amine,Benzene,Alcohol, name is 2-(Benzyl(methyl)amino)ethanol, and the molecular formula is C10H15NO, Recommanded Product: 2-(Benzyl(methyl)amino)ethanol.

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

Duclos, Marie-Christine published the artcileMethylation of Polyols with Trimethylphosphate in the Presence of a Lewis or Bronsted Acid Catalyst, Formula: C11H24O3, the publication is ChemSusChem (2018), 11(3), 547-551, database is CAplus and MEDLINE.

The alkylation of alcs. and polyols has been investigated with alkyl phosphates in the presence of a Lewis or Bronsted acid catalyst. The permethylation of polyols was developed under solvent-free conditions at 100 °C with either iron triflate or Aquivion PW98, affording the isolated products in yields between 52 and 95 %. The methodol. was also adjusted to carry out peralkylation with longer alkyl chains.

ChemSusChem published new progress about 70445-33-9. 70445-33-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 3-((2-Ethylhexyl)oxy)propane-1,2-diol, and the molecular formula is C11H24O3, Formula: C11H24O3.

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

Sams, Anette G. published the artcileDiscovery of N-{1-[3-(3-Oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): An Allosteric Muscarinic M₁ Receptor Agonist with Unprecedented Selectivity and Procognitive Potential, Related Products of alcohols-buliding-blocks, the publication is Journal of Medicinal Chemistry (2010), 53(17), 6386-6397, database is CAplus and MEDLINE.

The discovery and structure-activity relationship (SAR) of a series of allosteric muscarinic M₁ receptor agonists are described. Compound 17 (Lu AE51090) was identified as a representative compound from the series, based on its high selectivity as an agonist at the muscarinic M₁ receptor across a panel of muscarinic receptor subtypes. Furthermore, 17 displayed a high degree of selectivity when tested in a broad panel of G-protein-coupled receptors, ion channels, transporters, and enzymes, and 17 showed an acceptable pharmacokinetic profile and sufficient brain exposure in rodents in order to characterize the compound in vivo. Hence, in a rodent model of learning and memory, 17 reversed delay-induced natural forgetting, suggesting a procognitive potential of 17.

Journal of Medicinal Chemistry published new progress about 55346-97-9. 55346-97-9 belongs to alcohols-buliding-blocks, auxiliary class Fluoride,Nitro Compound,Benzene,Phenol, name is 4,5-Difluoro-2-nitrophenol, and the molecular formula is C6H3F2NO3, Related Products of alcohols-buliding-blocks.

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

Lee, Sie Huey published the artcileInhaled mucoactive particles with tailored architecture for enhanced aerodynamicity, stability and efficacy, Application In Synthesis of 23828-92-4, the publication is International Journal of Pharmaceutics (Amsterdam, Netherlands) (2019), 118740, database is CAplus and MEDLINE.

In respiratory and genetic disorders such as asthma, chronic obstructive pulmonary disease (COPD), chronic bronchitis and cystic fibrosis (CF), the lungs produce excess mucus, resulting in a thickened mass, which clogs up the airways and reduces airflow. Consequently, breathing becomes more difficult. Medications that break down the structure of mucus will be especially useful in managing the early symptoms of these diseases and preventing their progression into the more severe forms. This work therefore seeks to develop an inhaled mucoactive dry powder formulation that is efficacious on multiple fronts. As an innovative step, sodium chloride was used to tailor the surface architecture of ambroxol hydrochloride particles, such that the resulting angular features on the surfaces contributed to the creation of corrugated particles with enhanced aerodynamicity. The optimized spray-dried powder particles were of respirable-size (d₅₀ of 2.85 ± 0.15 μm) and moderately corrugated. When the crystalline powder was dispersed via an Aerolizer inhaler at 60 L/min, it gave a fine particle fraction (FPF) of ∼31%, which was a ten-fold improvement over the unmodified species (i.e. ambroxol hydrochloride alone). Tests on artificial sputum medium (ASM) showed that the optimized formulation was potentially useful in liquefying the mucus, which favorably pointed towards the effectiveness of the formulation. In addition, the formulation was also stable to moisture ingress (up to ∼60% RH) and had good flowability. Hence, the advent of angular adjuvant sodium chloride particles in a mucoactive formulation conferred a three-fold benefit to the product: (1) Improved aerodynamicity and flowability, (2) Enhanced moisture stability and (3) Synergistic mucolytic properties.

International Journal of Pharmaceutics (Amsterdam, Netherlands) published new progress about 23828-92-4. 23828-92-4 belongs to alcohols-buliding-blocks, auxiliary class Membrane Transporter/Ion Channel,Sodium Channel, name is trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol hydrochloride, and the molecular formula is C13H19Br2ClN2O, Application In Synthesis of 23828-92-4.

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

Forcellini, Elsa published the artcileSystematic study of the reactivity of (E)-4,4,4-trifluorobut-2-en-1-yl 4-methylbenzenesulfonate towards different classes of nucleophiles, Formula: C4H5F3O, the publication is Journal of Fluorine Chemistry (2015), 216-221, database is CAplus.

The alkylation of 4-phenylphenol, benzyl alc., thiols, primary and secondary amines, indole, and malonates by (E)-F₃CCH:CHCH₂OTs was studied; in most cases (4-phenylphenol, thiols, amines, malonates), alkylation of the nucleophiles was most effective using K₂CO₃ in MeCN, while none of the conditions tried were effective for indole and benzyl alc.

Journal of Fluorine Chemistry 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, Formula: C4H5F3O.

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

Del Grosso, Alessandro published the artcileSimple inexpensive boron electrophiles for direct arene borylation, Computed Properties of 239075-02-6, the publication is Chemical Communications (Cambridge, United Kingdom) (2011), 47(46), 12459-12461, database is CAplus and MEDLINE.

Borenium ions, stabilized by coordination of hindered aromatic amines, were shown to act as reactive electrophiles for direct borylation of activated arenes and heterocyclic compounds, such as indoles and thiophenes. 2,6-Lutidine complex of dichloroborenium, [2,6-Me₂C₅H₃N·BCl₂][AlCl₄] was isolated and characterized by single-crystal x-ray diffraction, featuring low degree of π-bonding and high electrophilicity. Friedel-Crafts-type reaction of ArH with BCl₃, catalyzed by AlCl₃ in the presence of N,N-dimethyltoluidine or 2,6-lutidine as borenium stabilizing agents, followed by esterification with 2.2-3 equiv of pinacol, gave pinacolboronates ArBpin (Ar = 1-TIPS-3-pyrrolyl, 1-methyl-3-indolyl, 2,2′-bithiophen-5-yl, thieno[3,2-b]thien-2-yl, 4-(phenyl)(p-tolyl)aminophenyl, etc.). Electrophilic direct borylation is facilitated, and arene substrate scope enhanced, by using electrophiles derived from inexpensive reagents; specifically an amine, BCl₃ and AlCl₃.

Chemical Communications (Cambridge, United Kingdom) published new progress about 239075-02-6. 239075-02-6 belongs to alcohols-buliding-blocks, auxiliary class Thiophene,Boronic acid and ester,Boronate Esters, name is 5,5′-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2′-bithiophene, and the molecular formula is C20H28B2O4S2, Computed Properties of 239075-02-6.

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