Category: alcohols-buliding-blocks

Savela, Risto published the artcileIron-Catalyzed Chlorination of Silanes, Category: alcohols-buliding-blocks, the publication is Organometallics (2012), 31(8), 3199-3206, database is CAplus.

A simple and highly efficient Fe-catalyzed method for the chlorination of silanes was developed. Using 0.5-2% of the Fe(III)-based catalyst FeCl₃ or Fe(acac)₃ in the presence of 1-1.5 equiv of acetyl chloride as the Cl donor, a large number of silanes, alkoxysilanes, and silanols were converted to the corresponding chlorosilanes in 50-93% yields. In contrast to earlier reported methods often suffering from expensive catalysts or use of stoichiometric metal salts, hazardous reagents, and reaction conditions, the presently described methodol. allows benign reaction conditions and simple workup while using only catalytic amounts of a readily available and economically viable Fe catalyst.

Organometallics published new progress about 17877-23-5. 17877-23-5 belongs to alcohols-buliding-blocks, auxiliary class Protection and Derivatization Reagent, name is Triisopropylsilanol, and the molecular formula is C9H22OSi, Category: alcohols-buliding-blocks.

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

Smirnov, Vladimir I. published the artcileCrystal and molecular structures of Si-(iodomethyl)silatranes with methyl substituents in β-position relative to the nitrogen atom, COA of Formula: C9H21NO3, the publication is Mendeleev Communications (2018), 28(3), 278-280, database is CAplus.

Crystal and mol. structures of two silatranes, 1-iodomethyl-3-methyl- and 1-iodomethyl-3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecanes, were determined by X-ray anal. Comparison of their structural and geometrical characteristics with those of other silatranes shows that the presence of Me substituents β-positioned to nitrogen atoms increases the length of the dative Si←N bond, whereas the introduction of iodine into the axial position of the silatrane slightly decreases the length of the Si←N bond.

Mendeleev Communications published new progress about 122-20-3. 122-20-3 belongs to alcohols-buliding-blocks, auxiliary class Organic Pigment, name is Triisopropanolamine, and the molecular formula is C16H20N2, COA of Formula: C9H21NO3.

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

Nageswara Rao, Desaboini published the artcileDiscovery of Quinoxaline-Based P1-P3 Macrocyclic NS3/4A Protease Inhibitors with Potent Activity against Drug-Resistant Hepatitis C Virus Variants, Recommanded Product: 1-Methylcyclobutan-1-ol, the publication is Journal of Medicinal Chemistry (2021), 64(16), 11972-11989, database is CAplus and MEDLINE.

The three pan-genotypic HCV NS3/4A protease inhibitors (PIs) currently in clin. use-grazoprevir, glecaprevir, and voxilaprevir-are quinoxaline-based P2-P4 macrocycles and thus exhibit similar resistance profiles. Using our quinoxaline-based P1-P3 macrocyclic lead compounds as an alternative chem. scaffold, we explored structure-activity relationships (SARs) at the P2 and P4 positions to develop pan-genotypic PIs that avoid drug resistance. A structure-guided strategy was used to design and synthesize two series of compounds with different P2 quinoxalines in combination with diverse P4 groups of varying sizes and shapes, with and without fluorine substitutions. Our SAR data and cocrystal structures revealed the interplay between the P2 and P4 groups, which influenced inhibitor binding and the overall resistance profile. Optimizing inhibitor interactions in the S4 pocket led to PIs with excellent antiviral activity against clin. relevant PI-resistant HCV variants and genotype 3, providing potential pan-genotypic inhibitors with improved resistance profiles.

Journal of Medicinal Chemistry published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Recommanded Product: 1-Methylcyclobutan-1-ol.

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

Rajesh, Sarigama published the artcileSynthetic ionizable aminolipids induce a pH dependent inverse hexagonal to bicontinuous cubic lyotropic liquid crystalline phase transition in monoolein nanoparticles, Recommanded Product: 2-Morpholinoethanol, the publication is Journal of Colloid and Interface Science (2021), 85-95, database is CAplus and MEDLINE.

A prospective class of materials for drug delivery is lyotropic liquid crystalline (LLC) nanoparticles, such as cubosomes and hexosomes. Efforts are being made to generate a pH dependent system, which exhibits slow release hexosomes (H2) at physiol. pH and relatively fast release cubosomes (Q2) at acidic disease sites such as in various cancers and bacterial infection (pH ∼ 5.5-6.5). Herein, we report the synthesis of nine ionizable aminolipids, which were doped into monoolein (MO) lipid nanoparticles. Using high throughput formulation and synchrotron small angle X-ray scattering (SAXS), the effects of aminolipid structure and concentration on the mesophase of MO nanoparticles at various pHs were determined As the pH changed from neutral to acidic, mesophases, could be formed in an order L2 (inverse micelles) → H2 → Q2. Specifically, systems with heterocyclic oleates exhibited the H2 to Q2 transition at pH 5.5-6.5. Furthermore, the phase transition pH could be fine-tuned by incorporating two aminolipids into the nanoparticles. Nanoparticles with a pH dependent phase transition as described in this study may be useful as drug delivery carriers for the treatment of cancers and certain bacterial infection.

Journal of Colloid and Interface Science 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

Pegolotti, J. A. published the artcileAllylic rearrangements. L. Reactions of α- and γ-trifluoromethylallyl alcohols with thionyl chloride and thermal decomposition of the chlorosulfinate intermediates, Synthetic Route of 83706-94-9, the publication is Journal of the American Chemical Society (1961), 3251-8, database is CAplus.

The reactions of α-(trifluoromethyl)allyl alc. (I) and γ-(trifluoromethyl)allyl alc. (II) with SOCl₂ in Et₂O and SOCl₂ were investigated. In the absence of amines, I in either solvent yielded α-(trifluoromethyl)allyl chlorosulfinate (III) only. With I, Bu₃N, and SOCl₂ (equimolar in ether) the products were 68% III and 32% γ-(trifluoromethyl)allyl chloride (IV) after 1 hr. The presence of Bu₃NHCl in the mixture gave small amounts of IV. II and SOCl₂ in ether yielded γ-(trifluoromethyl)allyl chlorosulfinate (V), which slowly gave IV on standing. In the presence of Bu₃N, II and SOCl₂ gave IV exclusively. III and V, the first isolable allylic chlorosulfinates outside of allyl chlorosulfinate itself, were thermally decomposed with no solvent and in n-decane and nitrobenzene and the rates of decomposition measured by the rate of evolution of SO₂ [compound, solvent, decompn, temperature, and rate (10⁵k. sec.^-1, extrapolated to 100°) given]: III, none (3 runs), 108-110° (103°, 105-106°), 6.5 (6.2, 7.3); III, nitrobenzene, 106-108°, 10.0; III, n-decane, 124°, 1.5; V, none (2 runs), 105° (139-142°), 126 (0.27); V, nitrobenzene (2 runs), 115-116° (118-120°), 5.1 (8.8). The insensitivity of the decomposition to solvent was explained in terms of a concerted reaction with predominant covalent character maintained in the intermediate through the rearrangement sequence. II was prepared by the procedure of McBee (CA 49, 10171b). I was prepared by addition of CF₃CHO to the Grignard reagent from vinyl bromide and Mg in tetrahydrofuran; I formed an azeotrope, b. 102-3°, with the solvent. Chromatography of the azeotrope gave I, b. 91.5°, n²⁵_D 1.3450. The α-napthylurethan of I m. 121-3°. Adding 8.9 g. SOCl₂ to 9.4 g. II and 13.9 g. Bu₃N over 30 min. at 0°, stirring 1 hr., then flash distilling gave IV, b. 82.5-83°, n²⁵_D 1.3610. γ-(Trifluoromethyl)allyl n-amyl sulfite (VI) was prepared by adding dropwise over 30 min. a mixture of 3.0 g. II and 1.9 g. anhydrous pyridine to a cooled (-20 to -30°) solution of 5.12 g. n-amyl chlorosulfinate in ether. H₂O was added after 45 min., the layers separated, the ether layer washed, dried, and distilled to yield 2.05 g. VI, b₄ 100-102°, n²⁵_D 1.4099. α-(Trifluoromethyl)allyl n-amyl sulfite (VII) was prepared similarly, b₅ 80-2°, n²⁵_D 1.4030. Addition of 4.86 g. SOCl₂ in ether to a stirred solution of 3.57 g. II in 60 ml. ether at 0° and distillation gave 1.23 g. V, b₆ 55°, n²⁵_D 1.4089. Reaction of V with n-amyl alc. gave VI. Addition of 3.1 g. I to 14.3 g. SOCl₂ and 5.3 g. Bu₃N over 45 min. at 0°, with stirring continued 1 hr., and distillation gave 2.78 g. III, b₃₉ 52°, n²⁵_D 1.4088. Reaction of III with n-amyl alc. gave VII. The refractive indexes of III and V did not change during 5 min. in the refractometer.

Journal of the American Chemical Society 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

Xu, Huanjun published the artcileReductive cleavage of inert aryl C-O bonds to produce arenes, COA of Formula: C15H16O3, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(61), 12212-12215, database is CAplus and MEDLINE.

Reductive cleavage of the aryl C-O bonds in various phenolic compounds and aryl ethers was achieved using LiAlH₄ combined with KOtBu and without any other catalysts or additives, solely producing arenes in high yields.

Chemical Communications (Cambridge, United Kingdom) 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 C11H10ClNO, COA of Formula: C15H16O3.

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

Xu, Wanling published the artcileElectrochemical hydrogenation of biomass-based furfural in aqueous media by Cu catalyst supported on N-doped hierarchically porous carbon, Synthetic Route of 111-29-5, the publication is Applied Catalysis, B: Environmental (2022), 121062, database is CAplus.

Electrochem. hydrogenation (ECH) is a particularly important and environmentally friendly approach to obtain biomass-based fuels and high value-added fine chems. without using external hydrogen. Herein, we reported a highly efficient and selective ECH of furfural (FF) into furfuryl alc. (FA) with Cu-based electrocatalyst in aqueous alk. media. Under the optimal conditions, FA selectivity close to 100% with 99% FF conversion and total Faradaic efficiency above 95% were obtained with the electrocatalyst. Mechanism investigation suggests an ECH mechanism for FA formation, which is highly potential-dependent to FA selectivity, requiring low and well-matched concentrations between active hydrogen (H_ads) species and FA radical on the Cu surface. Moreover, the electrocatalyst shows an excellent stability and recyclability during the eight-time consecutive recycling experiments, yielding a total amount of 1011 mg FA. This work thus highlights an important guidance for electrocatalytic upgrading of biomass-based platform mols. in an environmentally friendly way.

Applied Catalysis, B: Environmental 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 C20H23N3O2S, Synthetic Route of 111-29-5.

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

Liu, Jingping published the artcileFree-Radical-Promoted Dehydrogenative Coupling of Polyfluorinated Alcohol with Quinone, Chromone, and Coumarin, Name: 3,3,3-Trifluoropropan-1-ol, the publication is Organic Letters (2020), 22(12), 4844-4847, database is CAplus and MEDLINE.

A free-radical-mediated dehydrogenative cross-coupling reaction of polyfluorinated alc. with quinone, coumarin, and chromone was developed. It provides a sustainable and practical strategy for installation of fluorine atom into organic mols. by using polyfluorinated alcs.

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 C3H5F3O, Name: 3,3,3-Trifluoropropan-1-ol.

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

Wang, Bing-Lin published the artcileSynthesis of trifluoromethylated analogues of α-L-fucofuranose and α-L-4,6-dideoxyxylohexopyranose, Formula: C4H5F3O, the publication is Journal of Fluorine Chemistry (2006), 127(4-5), 580-587, database is CAplus.

Efficient strategy to trifluoromethylated trans-disubstituted alkene I was developed starting from com. available 4,4,4-trifluoro-3-oxo-butyric acid Et ester. 6-Deoxy-6,6,6-trifluorosugars II and III were synthesized from I in high stereoselectivity and in a straightforward fashion. The key steps were Sharpless asym. dihydroxylation, regioselective ring opening of trifluoromethylated cyclic sulfate, Horner-Wadsworth-Emmons reaction, oxidation and intramol. heterocyclization. It was noteworthy that the oxidation of alcs. followed by deprotection and acetylation gave the single isomer target mols. II and III, resp.

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 C7H10N2O2, Formula: C4H5F3O.

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

Jung, Heesun published the artcileCpG oligonucleotide and α-D-mannose conjugate for efficient delivery into macrophages, Application of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, the publication is Applied Biological Chemistry (2016), 59(5), 759-763, database is CAplus.

For improved intracellular uptake of CpG ODN into macrophages, we developed CpG ODN and mannose conjugate (CpG-Man conjugate) via simple conjugation of α-D-mannose to CpG ODN. CpG-Man conjugate showed greatly enhanced intracellular uptake by 2.1-fold into macrophages, compared to CpG ODN in a TLR-9 receptor-specific manner. In addition, internalized CpG-Man conjugate successfully triggered TNF-α release in macrophages. Taken together, the CpG-Man conjugate can serve as the promising delivery systems of CpG ODN into immune cells as a candidate adjuvant.

Applied Biological Chemistry published new progress about 96345-79-8. 96345-79-8 belongs to alcohols-buliding-blocks, auxiliary class Sugar Units,Gal and Man, name is (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C13H15NO6S, Application of (2R,3S,4S,5S,6R)-2-(Hydroxymethyl)-6-(4-isothiocyanatophenoxy)tetrahydro-2H-pyran-3,4,5-triol.

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