Tag: M.W=200-250

Enache, Teodor Adrian published the artcileElectrochemical behavior of triflusal, aspirin and their metabolites at glassy carbon and boron doped diamond electrodes, Synthetic Route of 328-90-5, the publication is Combinatorial Chemistry & High Throughput Screening (2010), 13(7), 569-577, database is CAplus and MEDLINE.

The electrochem. behavior of triflusal (TRF) and aspirin (ASA), before and after hydrolysis in water and in alk. medium using two different electrode surfaces, glassy carbon and boron doped diamond, was studied by differential pulse voltammetry over a wide pH range. The hydrolysis products were 2-(hydroxyl)-4-(trifluoromethyl)-benzoic acid (HTB) for triflusal and salicylic acid (SA) for aspirin, which in vivo represent their main metabolites. The hydrolysis processes were also followed by spectrophotometry. The UV results showed complete hydrolysis after one hour for TRF and after two hours for ASA in alk. solution The glassy carbon electrode enables only indirect determination of TRF and ASA through the electrochem. detection of their hydrolysis products HTB and SA, resp. The oxidation processes of HTB and SA are pH dependent and involve different numbers of electrons and protons. Moreover, the difference between the oxidation peak potential of SA and HTB was equal to 100 mV in the studied pH range from 1 to 8 due to the CF₃ of the aromatic ring of HTB mol. Due to its wider oxidation potential range, the boron doped diamond electrode was used to study the direct oxidation of TRF and ASA, as well as of their resp. metabolites HTB and SA.

Combinatorial Chemistry & High Throughput Screening published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Synthetic Route of 328-90-5.

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

Bennett, Steven H. published the artcileDifunctionalization of C-C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins, Category: alcohols-buliding-blocks, the publication is Journal of the American Chemical Society (2020), 142(39), 16766-16775, database is CAplus and MEDLINE.

Difunctionalization reactions of C-C σ-bonds have the potential to streamline access to mols. that would otherwise be difficult to prepare However, the development of such reactions is challenging because C-C σ-bonds are typically unreactive. Exploiting the high ring-strain energy of polycyclic carbocycles is a common strategy to weaken and facilitate the reaction of C-C σ-bonds, but there are limited examples of highly strained C-C σ-bonds being used in difunctionalization reactions. We demonstrate that highly strained bicyclo[1.1.0]butyl boronate complexes (strain energy ca. 65 kcal/mol), which were prepared by reacting boronic esters with bicyclo[1.1.0]butyl lithium, react with electrophiles to achieve the diastereoselective difunctionalization of the strained central C-C σ-bond of the bicyclo[1.1.0]butyl unit. The reaction shows broad substrate scope, with a range of different electrophiles and boronic esters being successfully employed to form a diverse set of 1,1,3-trisubstituted cyclobutanes (>50 examples) with high diastereoselectivity. The high diastereoselectivity observed has been rationalized based on a combination of exptl. data and DFT calculations, which suggests that sep. concerted and stepwise reaction mechanisms are operating, depending upon the migrating substituent and electrophile used.

Journal of the American Chemical Society published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Category: alcohols-buliding-blocks.

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

Monsigny, Louis published the artcileEfficient reductive depolymerization of hardwood and softwood lignins with Brookhart’s iridium catalyst and hydrosilanes, Product Details of C15H16O3, the publication is Green Chemistry (2018), 20(9), 1981-1986, database is CAplus.

Efficient catalytic reduction of lignin model mols. and reductive depolymerization of softwood and hardwood lignins is presented with the iridium based Brookhart’s catalyst and hydrosilanes R₃SiH as reductant. This catalyst displays increased stability and selectivity in comparison to the B(C₆F₅)₃/hydrosilane system and it enables a convergent reductive depolymerization of wood lignins to isolable mono-aromatics

Green Chemistry published new progress about 70110-65-5. 70110-65-5 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Alcohol,Ether,Benzene Compounds, name is 2-Phenoxy-1-phenylpropane-1,3-diol, and the molecular formula is C15H16O3, Product Details of C15H16O3.

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

Zheng, Ran published the artcileMicrowave-assisted efficient synthesis of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl via 1,3-dipolar cycloaddition, Recommanded Product: 3-(2-Chlorophenyl)-5-isoxazolemethanol, the publication is Molecular Diversity (2020), 24(2), 423-435, database is CAplus and MEDLINE.

An efficient strategy for synthesizing of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl under microwave radiation was reported. The reactive regioselectivity was improved by changing mainly the solvent and acid-binding agent. 3-(2-Chloropyridin-3-yl)-5-(((3-substituted Ph isoxazol-5-yl)methoxy)methyl)isoxazoles were synthesized in 31-92% yields and were characterized by FT-IR, HRMS, ¹H and ¹³C NMR spectroscopy. The single crystal of 3-(2-chloropyridin-3-yl)-5-(((3-(p-tolyl)isoxazol-5-yl)methoxy)methyl)isoxazole was obtained and the structure of compound was also determined by X-ray diffraction technique. Weak intra- and intermol. C-H···O interactions and a C-H···π interaction link mols. into a three-dimensional network. The results showed that the synthesized compounds belonged to triclinic system, and their regioselectivity depended on the solvent and acid-binding agent. The merits of this method include the environmentally friendly, efficient, simple operation, and higher regional selectivity. An efficient synthesis of 3-substituted bis-isoxazole ethers was developed via 1,3-dipolar cycloaddition reaction starting from 3-substituted phenyl-5-((prop-2-yn-1-yloxy)methyl)isoxazoles and (Z)-2-chloro-N-hydroxynicotinimidoyl chloride using NaHCO₃ as an acid-binding agent in THF solvent-dissolved trace water under catalyst-free microwave-assisted conditions.

Molecular Diversity published new progress about 438565-33-4. 438565-33-4 belongs to alcohols-buliding-blocks, auxiliary class Isoxazole,Chloride,Benzene,Alcohol, name is 3-(2-Chlorophenyl)-5-isoxazolemethanol, and the molecular formula is C9H4F6O, Recommanded Product: 3-(2-Chlorophenyl)-5-isoxazolemethanol.

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

Wang, Shengzheng published the artcileScaffold diversity inspired by the natural product evodiamine: discovery of highly potent and multitargeting antitumor agents, Recommanded Product: 2-Hydroxy-4-(trifluoromethyl)benzoic acid, the publication is Journal of Medicinal Chemistry (2015), 58(16), 6678-6696, database is CAplus and MEDLINE.

A critical question in natural product-based drug discovery is how to translate the product into drug-like mols. with optimal pharmacol. properties. The generation of natural product-inspired scaffold diversity is an effective but challenging strategy to investigate the broader chem. space and identify promising drug leads. Extending the efforts to the natural product evodiamine, a diverse library containing 11 evodiamine-inspired novel scaffolds and their derivatives were designed and synthesized. Most of them showed good to excellent antitumor activity against various human cancer cell lines. In particular, 3-chloro-10-hydroxyl thio-evodiamine I showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound I is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery.

Journal of Medicinal Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C14H17BFNO2, Recommanded Product: 2-Hydroxy-4-(trifluoromethyl)benzoic acid.

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

Pospisil, Jan published the artcileOxidation of catechol. IV. Oxidation of 4-tert-octylcatechol, HPLC of Formula: 1139-46-4, the publication is Chemicke Listy pro Vedu a Prumysl (1958), 939-47, database is CAplus.

cf. C.A. 52, 4546g. Oxidation of 4-tert-octylcatechol (I) (tert-octyl = R = Me₃CCH₂CMe₂) with O or alk. H₂O₂ gave 2-hydroxy-5-tert-octyl-1,4-benzoquinone (II), also obtained by oxidation of 4-tert-octyl-1,2-benzoquinone (III). The oxidation of I is assumed to proceed through intermediate 1,2,4-trihydroxy-5-tert-octylbenzene (IV) to II. A similar mechanism is proposed for the oxidation of catechol (V) to 2,5-dihydroxy-1,4-benzoquinone (VI). Alkylation of pyrogallol (VII) with di-isobutylene (VIII) gave 5-tert-octylpyrogallol (IX) whose oxidation with Ag₂O yielded 6-hydroxy-4-tert-octyl-1,2-benzoquinone (X). Dissolving 110 g. resublimed V in 448 g. hot VIII, treating the solution with 0.2 ml. concentrated H₂SO₄, stirring the mixture 2.5 hrs. at 105-15°, cooling, filtering off the product with suction, and washing with H₂O yielded 167.6 g. I, m. 108° (ligroine). Adding a solution of 4.5 g. I in 220 ml. Et₂O to a mixture of 100 ml. Et₂O, 5 g. anhydrous Na₂SO₄, and Ag₂O prepared from 135 g. AgNO₃, shaking 5 min., filtering, and evaporating gave 4.29 g. III, m. 121-1.5° (Et₂O). Acetylation of 2.2 g. I by heating with 6 ml. Ac₂O and 0.1 ml. concentrated H₂SO₄ 20 min. on the steam-bath gave 1.8 g. 1,2-diacetoxy-4-tert-octylbenzene, m. 49.5°. The same compound was also obtained by boiling for 10 min. a mixture of 0.44 g. III, 1 g. anhydrous NaOAc, 1.0 g. Zn dust, and 12 ml. Ac₂O. To oxidize I, O was passed into a solution of 68 g. KOH in 300 ml. 75% MeOH at a rate of 0.2-0.3 l./min. at 30°. After 15 min., 10 g. I in 100 ml. 75% MeOH was added over a period of 2.5 hrs. The initial blue color turned red. The red clear solution was diluted with 300 ml. H₂O, 300 g. ice was added, and the mixture acidified with concentrated HCl. The solution turned yellow and a yellow product precipitated Evaporation of the MeOH in vacuo yielded another crop of II, m. 133.5-4.5° (decomposition) (petr. ether) (7.45 g., 70.1% total). Dissolving 4.5 g. I in 50 ml. 5% solution of KOH in 50% MeOH, treating this solution at 40° with 7 ml. 40% H₂O₂ for 30 min., stirring the mixture 1.5 hrs., decanting the red solution from resinous material, diluting it to a 10-fold volume with ice and H₂O, and acidifying with HCl gave 69.8% II. The same compound was obtained also by oxidation of 0.22 g. III in methanolic solution of KOH (containing 4.5 g. KOH in 45 ml. 75% MeOH) by passing 0.15-0.2 l./min. O through the solution 1.5 hrs. (yield 41.3%) or by treating 0.5 g. III in 2.2 ml. MeOH with 2.5 ml. 40% aqueous KOH and 1.4 ml. 40% H₂O₂ 1 hr. at 40° (yield 15.3%, 0.08 g.). Absorption of II in 0.1N aqueous KOH showed log ε 4.086 at 285 mμ, and log ε 3.216 at 495 mμ. Heating 1 g. II with 5 ml. Ac₂O and 0.1 ml. concentrated H₂SO₄ 2 hrs. at 45° and diluting the mixture after 20 hrs. with 20 ml. H₂O yielded 0.95 g. 2-acetoxy-5-tert-octyl-1,4-benzoquinone (XI), m. 89.5-90° (petr. ether). Dissolving 0.2 g. XI in 5 ml. Ac₂O, adding 0.5 g. Zn dust and 0.5 g. anhydrous NaOAc, refluxing the mixture 30 min., filtering off the Zn, and diluting the filtrate with 25 ml. H₂O and 25 g. ice gave 0.22 g. triacetate (XII) of IV, m. 88.5° (petr. ether). The same compound was obtained by treating similarly 2 g. II in 25 ml. Ac₂O with 2.5 g. Zn dust and 2.5 g. NaOAc; yield 2.62 g. Hydrogenation of 0.11 g. II in 20 ml. glacial AcOH and 40 ml. Ac₂O over PtO₂ and heating the mixture with 0.2 ml. concentrated H₂SO₄ 20 min. under H gave XII. If the hydrogenation was carried out in MeOH, the colorless solution of IV formed was reoxidized in contact with air. Heating 30 g. VII with 172 g. VIII and 0.1 ml. concentrated H₂SO₄ 3 hrs. at 105-15° gave 30.7 g. (51.7%) IX, m. 104° (ligroine). Shaking 1.2 g. IX in 100 ml. Et₂O with 12 g. Ag₂O and 10 g. anhydrous Na₂SO₄ in 50 ml. Et₂O for 10 min. gave a red solution of X whose reductive acetylation by heating with 5 ml. Ac₂O, 0.5 g. NaOAc, and 0.5 g. Zn dust in 30 ml. C₆H₆ gave 1,2,3-triacetoxy-5-tert-octylbenzene, m. 71° (petr. ether). The same compound was also obtained by allowing 0.37 g. III to stand 24 hrs. at 20° with 10 ml. Ac₂O and 0.1 ml. H₂SO₄ or by heating 1 g. IX with 8 ml. Ac₂O and 0.1 ml. H₂SO₄ 10 min. on the steam bath (yield 1.25 g.). Heating 0.28 g. VI, 6 ml. Ac₂O, and 0.1 ml. H₂SO₄ 2 hrs. at 50° and diluting the mixture after 20 hrs. with ice and H₂O gave 0.27 g. 2,5-diacetoxy-1,4-benzoquinone (XIII), m. 151-2° (decomposition) (AcOH). Hydrogenation of 0.14 g. VI in 40 ml. MeOH over PtO₂ at 18° gave impure 1,2,4,5-tetrahydroxybenzene whose acetylation with 5 ml. Ac₂O and 1 drop H₂SO₄ gave tetraacetate, m. 226° (AcOH).

Chemicke Listy pro Vedu a Prumysl published new progress about 1139-46-4. 1139-46-4 belongs to alcohols-buliding-blocks, auxiliary class Benzene,Phenol, name is 4-(2,4,4-Trimethylpentan-2-yl)benzene-1,2-diol, and the molecular formula is C14H22O2, HPLC of Formula: 1139-46-4.

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

Ryczaj, Klaudia published the artcilePotentially harmful substances in moisturizers, COA of Formula: C11H24O3, the publication is Journal of Allergy and Clinical Immunology (2021), 148(2), 653-654, database is CAplus and MEDLINE.

A review. Despite the promising results of preliminary studies and hope for preventing atopic dermatitis (AD) and food allergy (FA) in high-risk infants by emollient application from their first days of life, further analyses failed to confirm the validity of such an approach. Haptens are low-mol.-weight chems. that may cause irritant or allergic contact dermatitis or subclin. skin barrier function changes. In 13 of the 17 emollients, at least 1 hapten was identified. The haptens found in the preparations were as follows: lanolin, iso-Pr myristate, phenoxyethanol, benzyl alc., sorbitan oleate, sorbitan sesquioleate, tocopheryl acetate, tocopherol, sorbic acid, propylene glycol, panthenol, ethylhexyl glycerin, cetearyl alc., cetyl alc., and stearyl alc. Thus, it is possible that chronic use of moisturizers containing haptens may lead to a vicious cycle of inflammation and skin barrier disruption that requires repeated applications of products

Journal of Allergy and Clinical Immunology 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, COA of Formula: C11H24O3.

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

Cortes-Arriagada, Diego published the artcileInsights into the luminescent properties of anionic cyclometalated iridium(III) complexes with ligands derived from natural products, Formula: C8H5F3O3, the publication is International Journal of Quantum Chemistry (2018), 118(17), n/a, database is CAplus.

In the search of remarkable anionic electroluminescent semiconductors to be applied in energy conversion devices such as Light Emitting Electrochem. Cells, we report the electronic, photophys., and charge injection/transfer properties of a series of cyclometalated iridium(III) complexes through a DFT/TD-DFT procedure. The proposed semiconductors involve bidentated ligands based on natural products (salicylic acid and boldine), and phenylpyridine and phenylpyrazole as the cyclometalating units. The proposed compounds emit in the range of 446 to 571 nm, where the boldine based compounds have red-shifted emissions compared to their analogs with salicylic acid. Blue phosphors were obtained by the use of phenylpyrazole units; however, the ligand field is weak in these cases compared to the ligand field exerted by the phenylpyridine ligands. The latter allows the accessibility to the radiationless states for emitters below 495 nm as a result of the increased stability of the metal centered excited states; consequently, the luminescent quantum yield could be decreased. Conversely, the semiconductors with phenylpyridine units show a restricted accessibility to radiationless processes, which could result in emitters with a high luminescent quantum yield and low non-radiative constants Finally, the proposed anionic semiconductors show a better balance between hole/electron transfer rate compared to related cationic Ir(III) complexes; while, the easier hole-electron injection is favored for semiconductors with salicylic acid and phenylpyridine units.

International Journal of Quantum Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Formula: C8H5F3O3.

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

Giroud, Maude published the artcileRepurposing a Library of Human Cathepsin L Ligands: Identification of Macrocyclic Lactams as Potent Rhodesain and Trypanosoma brucei Inhibitors, Synthetic Route of 328-90-5, the publication is Journal of Medicinal Chemistry (2018), 61(8), 3350-3369, database is CAplus and MEDLINE.

Rhodesain (RD) is a parasitic, human cathepsin L (hCatL) like cysteine protease produced by Trypanosoma brucei (T. b.) species and a potential drug target for the treatment of human African trypanosomiasis (HAT). A library of hCatL inhibitors was screened, and macrocyclic lactams were identified as potent RD inhibitors (K_i < 10 nM), preventing the cell-growth of Trypanosoma brucei rhodesiense (IC₅₀ < 400 nM). SARs addressing the S2 and S3 pockets of RD were established. Three cocrystal structures with RD revealed a noncovalent binding mode of this ligand class due to oxidation of the catalytic Cys 25 to a sulfenic acid (Cys-SOH) during crystallization The P-glycoprotein efflux ratio was measured and the in vivo brain penetration in rats determined When tested in vivo in acute HAT model, the compounds permitted up to 16.25 (vs. 13.0 for untreated controls) mean days of survival.

Journal of Medicinal Chemistry published new progress about 328-90-5. 328-90-5 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Carboxylic acid,Benzene,Phenol, name is 2-Hydroxy-4-(trifluoromethyl)benzoic acid, and the molecular formula is C8H5F3O3, Synthetic Route of 328-90-5.

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

Panferova, Liubov I. published the artcileLight-Mediated Sulfur-Boron Exchange, Category: alcohols-buliding-blocks, the publication is Organic Letters (2021), 23(10), 3919-3922, database is CAplus and MEDLINE.

Photochem. organocatalytic substitution of pyridylthio group in alkyl tetrafluoropyridinyl thioethers RS-4-C₅F₄N with bis(catecholato)diboron followed by treatment with pinacol and triethylamine affording pinacol boronic esters RBpin is described. The reaction is promoted by an organic photocatalyst, 2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile (3DPA2FBN) under irradiation with 400 nm light, and works with primary, secondary, and tertiary sulfides. The electron depleting character of the fluorinated pyridine fragment plays an important role in generating alkyl radicals.

Organic Letters published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Category: alcohols-buliding-blocks.

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