Month: February 2023

Production of (R)-chiral alcohols by a hydrogen-transfer bioreduction with NADH-dependent Leifsonia alcohol dehydrogenase (LSADH) was written by Inoue, Kousuke;Makino, Yoshihide;Itoh, Nobuya. And the article was included in Tetrahedron: Asymmetry in 2005.COA of Formula: C8H9ClO This article mentions the following:

Alc. dehydrogenase (LSADH) isolated from Leifsonia sp. S749 was used to produce (R)-chiral alcs. The enzyme with a broad substrate range reduced various prochiral ketones and keto esters to yield optically active secondary alcs. with a high enantiomeric excess. LSADH transferred the pro-S hydrogen of NADH to the carbonyl moiety of Ph trifluoromethyl ketone (13) through its re face to give (S)-1-phenyl-2,2,2-trifluoroethanol (40). LSADH was able to efficiently reproduce NADH when 2-propanol was used as a hydrogen donor in the reaction mixture In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9COA of Formula: C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.COA of Formula: C8H9ClO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Photochemical C-H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms was written by Rammal, Fatima;Gao, Di;Boujnah, Sondes;Hussein, Aqeel A.;Lalevee, Jacques;Gaumont, Annie-Claude;Morlet-Savary, Fabrice;Lakhdar, Sami. And the article was included in ACS Catalysis in 2020.Reference of 1122-71-0 This article mentions the following:

Described herein is an efficient approach for C-H silylation and hydroxymethylation of pyridines and related heterocycles by the combination of silanes or methanol with readily available N-methoxypyridinium ions with a low catalyst loading (2 mol %) under blue light irradiation The synthetic importance of the developed reactions is demonstrated by the synthesis of biol. relevant compounds ESR spectroscopy, quantum yield measurements, and d.-functional theory calculations allowed to understand reaction mechanisms of both photocatalytic reactions. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Reference of 1122-71-0).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Reference of 1122-71-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Design of hydrophilic photocleavage o-nitrobenzyl acrylate-modified nanogels with outstanding biocompatibility prepared by RAFT polymerization for drug carrier was written by Xin, Fuhua;Wei, Meng;Jiang, Shengling;Gao, Yanjing;Nie, Jun;Wu, Yuejiao;Sun, Fang. And the article was included in European Polymer Journal in 2020.Formula: C7H7NO4 This article mentions the following:

Three kinds of hydrophilic photocleavage o-nitrobenzyl acrylate-modified nanogels with different particle size and narrow particle size distribution (1.8-0.24) were designed and synthesized by reversible addition-fragmentation chain transfer radical (RAFT) polymerization based on methoxy polyethylene glycol methacrylate (MPEGMA) and UV-light responsive crosslinker 5-(acryloyloxy)-2-nitrobenzyl acrylate (ONB) prepared with acryloyl chloride and 2-hydroxy-5-nitrobenzyl alc. The influences of particle size and distribution of the nanogel on its loading, encapsulation and photo-responsive release properties were investigated via the measurements of the final drug loading, the encapsulation efficiency and final cumulative release of coumarin 102 in the nanogel. The final drug loading, the encapsulation efficiency and the final cumulative release of coumarin 102 in the nanogel NG-ONB-300 with narrow particle size distribution were nearly twice more than those in the nanogel NG-ONB-300_AIBN with wide particle size distribution (0.33) at the same concentration of coumarin 102 and reached 8.31%, 39.5% and 67%, resp. With the increase of the particle size of the nanogel, the drug loading and encapsulation efficiency of the nanogel were decreased. Significantly, the in vitro cytotoxicity of the nanogel was also evaluated against HeLa cervical cancer cells by the MTT cell viability assay and its cell viability at different concentrations was greater than 91%, demonstrating that the photocleavage nanogel has an excellent biocompatibility and great potential in drug delivery fields. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Formula: C7H7NO4).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. A multistep synthesis may use Grignard-like reactions to form an alcohol with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the desired functionality.Formula: C7H7NO4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

New Selective Phosphodiesterase 4D Inhibitors Differently Acting on Long, Short, and Supershort Isoforms was written by Bruno, Olga;Romussi, Alessia;Spallarossa, Andrea;Brullo, Chiara;Schenone, Silvia;Bondavalli, Francesco;Vanthuyne, Nicolas;Roussel, Christian. And the article was included in Journal of Medicinal Chemistry in 2009.Synthetic Route of C5H13NO This article mentions the following:

The lack of selective inhibitors toward the long, short, or supershort phosphodiesterases (PDE4s) prevented researchers from carefully defining the connection between different enzyme isoforms, their brain localization, and their role in neurodegenerative diseases such as Alzheimer’s disease (AD). In the search for new therapeutic agents for treating memory and learning disorders, we synthesized new rolipram related PDE4 inhibitors, which had some selectivity toward the long form PDE4D3. The first series was synthesized as racemate and then resolved by semipreparative HPLC on chiral supports. Herein we report the synthetic pathways to obtain rolipram related compounds and their biol. activities and some SAR considerations that provide some insights and hints for the structural requirements for PDE4D subtype selectivity and enzyme inhibition. In the experiment, the researchers used many compounds, for example, 3-Amino-3-methylbutan-1-ol (cas: 42514-50-1Synthetic Route of C5H13NO).

3-Amino-3-methylbutan-1-ol (cas: 42514-50-1) belongs to alcohols. Alcohols are weak acids. The most acidic simple alcohols (methanol and ethanol) are about as acidic as water, and most other alcohols are somewhat less acidic. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Synthetic Route of C5H13NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Design and Synthesis of Novel Spiro Derivatives as Potent and Reversible Monoacylglycerol Lipase (MAGL) Inhibitors: Bioisosteric Transformation from 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl Moiety was written by Ikeda, Shuhei;Sugiyama, Hideyuki;Tokuhara, Hidekazu;Murakami, Masataka;Nakamura, Minoru;Oguro, Yuya;Aida, Jumpei;Morishita, Nao;Sogabe, Satoshi;Dougan, Douglas R.;Gay, Sean C.;Qin, Ling;Arimura, Naoto;Takahashi, Yasuko;Sasaki, Masako;Kamada, Yusuke;Aoyama, Kazunobu;Kimoto, Kouya;Kamata, Makoto. And the article was included in Journal of Medicinal Chemistry in 2021.Application of 142253-56-3 This article mentions the following:

The therapeutic potential of monoacylglycerol lipase (MAGL) inhibitors in central nervous system-related diseases has attracted attention worldwide. However, the availability of reversible-type inhibitor is still limited to clarify the pharmacol. effect. Herein, we report the discovery of novel spiro chem. series as potent and reversible MAGL inhibitors with a different binding mode to MAGL using Arg57 and His121. Starting from hit compound 1 and its co-crystal structure with MAGL, structure-based drug discovery (SBDD) approach enabled us to generate various spiro scaffolds like 2a (azetidine-lactam), 2b (cyclobutane-lactam), and 2d (cyclobutane-carbamate) as novel bioisosteres of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl moiety in 1 with higher lipophilic ligand efficiency (LLE). Optimization of the left hand side afforded 4f (I) as a promising reversible MAGL inhibitor, which showed potent in vitro MAGL inhibitory activity (IC₅₀ 6.2 nM), good oral absorption, blood-brain barrier penetration, and significant pharmacodynamic changes (2-arachidonoylglycerol increase and arachidonic acid decrease) at 0.3-10 mg/kg, po. in mice. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Application of 142253-56-3).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. The oxygen atom of the strongly polarized O―H bond of an alcohol pulls electron density away from the hydrogen atom. This polarized hydrogen, which bears a partial positive charge, can form a hydrogen bond with a pair of nonbonding electrons on another oxygen atom. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Application of 142253-56-3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A Numerical and Experimental Performance Assessment of a Single-Phase Supersonic Ejector was written by Hamzaoui, Malek;Nesreddine, Hakim;Aidoun, Zine. And the article was included in Arabian Journal for Science and Engineering in 2022.Quality Control of 1,2-Propanediol This article mentions the following:

This paper proposes an integrated numerical-exptl. study of a fixed geometry ejector designed for a cooling system activated by waste heat. Ejector operation is analyzed for cases of imposed input and output sets of conditions in terms of pressures and/or temperatures Experiments with constant primary conditions and secondary temperature were conducted in a range of outlet pressures for model validation purposes. A parametric anal. was then performed for constant pressure and temperature conditions at both inputs (primary and secondary) by varying the outlet pressure. For each test case, performance in terms of entrainment ratio, local parameters distributions (P, M, τ) and the internal flow structure were analyzed in an attempt to establish a link between the external constraints, the flow structure, the operation stability and performance within the range of cooling applications. The ranges of operating conditions investigated were P_p = 4.77 bar, T_p = 83°C and, resp., 1.7 ≤ Pc ≤ 2.4 bar, 12.5°C ≤ Te ≤ 16.5°C, at saturation Exptl. entrainment ratio, ER_exp in the range of 0.12-0.22 was numerically simulated within ± 10%. It was shown that both the ejector operation and the internal flow configurations were sensitive to backpressure. More particularly, an optimal backpressure exists to which corresponds an on-design conditions with maximized entrainment ratio and a shock-wave train located at the end of the mixing chamber. A backpressure increase sets the ejector in off design. This mode of operation is characterized by a shift of the shock train toward the inlets, a disturbance of the flow configuration, a diminution of the entrainment ratio and a deterioration of the operation stability. On the other hand, a backpressure decrease does not affect the ejector stability of operation at its maximum entrainment ratio for the prevailing conditions. In the experiment, the researchers used many compounds, for example, 1,2-Propanediol (cas: 57-55-6Quality Control of 1,2-Propanediol).

1,2-Propanediol (cas: 57-55-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Quality Control of 1,2-Propanediol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Mechanisms of solvent separation using sugars and sugar alcohols was written by Marshall, Tatianna;Marangoni, Alejandro G.;Laredo, Thamara;Al-Abdul-Wahid, M. Sameer;Pensini, Erica. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2022.Formula: C4H10O4 This article mentions the following:

This study uses sugars (dextrose, sucrose, ribose, fructose and mannose) and sugar alcs. (maltitol, erythritol, sorbitol, xylitol) to sep. water from THF (THF) and acetonitrile (AN). Bottle tests and NMR (NMR) show that above 0.25 M all sugars and sugar alcs. effectively sep. water from either THF or AN. At 0.5 M concentrations, maltitol and sucrose yield a non-negligible interfacial tension between AN and water, while the interfacial tension is negligible with all other compounds This indicates that while all compounds have similar separation effectiveness above a benchmark concentration, maltitol and sucrose (which are dimers) have a stronger effect on water structure compared to the other compounds tested (which are monomers). Attenuated Total Reflectance – Fourier Transform IR spectroscopy (ATR-FTIR) was used to explain solvent separation, based on the effect of sugars on hydrogen bonding (H-bonding) and on the nitrile band. The H-bonding peak was deconvolved into peaks representative of different water clusters, comprised of water mols. donating and accepting a different number of H-bonds. Principal component anal. (PCA) shows that single H-bond donors (SD) (at approx. 3200 cm^-1) and double H-bond donor (DD) (at approx. 3400 cm^-1) are most affected by maltitol and sucrose. All sugars tested induce a blue shift of the H-bonding of absorbance peaks for DD and SD, in either water or in mixtures of water-AN and water-THF. This indicates that they strengthen H-bonding in these clusters. The effect of all sugars is comparable when concentrations are expressed as OH equivalent Sugars increase the ratio between the amplitude A of SD relative to DD, and SD are most effective at structuring water. The difference between the ratio A(SD)/A(DD) after and before sugar addition is lowest in water (≈0.9), followed by THF-water mixtures (≈1.1) and AN-water mixtures (≈1.2). This indicates that solvents enhance the effect of sugars on H bonding. This is likely because sugars are not soluble in either THF or AN, which therefore excludes them and promotes their interactions with water. In turn, water-sugar H-bonding weakens interactions between AN-water or THF-water, leading to solvent separation The anal. of the nitrile band shows that sugars and sugar alcs. increase the relative amount of free nitrile, which is correlated to weaker interactions between AN and water. Maltitol and sucrose display approx. two times the relative amount of free nitrile compared to dextrose and erythritol. Our study confirms that sugars and sugar alcs. weaken solvent-water interactions, and reveals that they sep. solvents by increasing the proportion of SD relative to DD. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Formula: C4H10O4).

(2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Converting an alcohol to an alkene requires removal of the hydroxyl group and a hydrogen atom on the neighbouring carbon atom. Dehydrations are most commonly carried out by warming the alcohol in the presence of a strong dehydrating acid, such as concentrated sulfuric acid.Formula: C4H10O4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Integrating photogenerated charge carriers for hydrogen production on noble-metal free dual-photocatalyst under visible light was written by Wang, Yang;Yang, Jiawen;Qin, Xiru;Zhuang, Jiayi;Yin, Wujie;Chen, Tingting;Yao, Yong. And the article was included in Composites, Part B: Engineering in 2022.SDS of cas: 873-76-7 This article mentions the following:

Simultaneous using photogenerated electrons and holes in one reaction to produce H₂ and value-added organic intermediates hold great promise for the green synthesis of chems. and clean energy. Herein, we designed an efficient, noble-metal free and dual-photocatalyst Ni/Zn₃In₂S₆ for simultaneous aldehydes synthesis and H₂ production under visible light irradiation Due to the reasonable band structure of Zn₃In₂S₆ and the Schottky barrier established between Zn₃In₂S₆ and Ni, the photogenerated electrons and holes with suitable redox potentials can be spatially separated and efficiently transferred. Thereby, alcs. can be highly selective oxidized into corresponding aldehydes or carbonyl compounds at Zn₃In₂S₆ by the holes, and the released protons can be rapidly reduced into H₂ at Ni by the electrons. The H₂ evolution of the optimal Ni/Zn₃In₂S₆ can reach up to 277.2μmol h^-1, which is about 6.5 and 5.3 times as high as that of the pristine Zn₃In₂S₆ and the Pt/Zn₃In₂S₆, resp. Ni/Zn₃In₂S₆ also shows the stability and general applicability for other aromatic and non-aromatic alcs. Compared with NiS_x, NiO_x and Ni²⁺ cocatalysts, the metallic state of Ni is the key to achieving these photoredox reactions for effective utilization of photoexcited holes and electrons in one reaction system. During the photoredox reactions, two protons derived from O-H and Cα-H are abstracted from alcs. and then reduced into H₂ by the photogenerated electrons. At the same time, alcs. are oxidized into aldehydes or carbonyl compounds by the photogenerated holes. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7SDS of cas: 873-76-7).

(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. Under appropriate conditions, inorganic acids also react with alcohols to form esters. To form these esters, a wide variety of specialized reagents and conditions can be used. Tertiary alcohols cannot be oxidized at all without breaking carbon-carbon bonds, whereas primary alcohols can be oxidized to aldehydes or further oxidized to carboxylic acids.SDS of cas: 873-76-7

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Sequence of hydrogen replacement by lithium or halogen in 2,6-dimethylpyridine was written by Karpman, Ya. S.;Azimov, V. A.;Anisimova, O. S.;Yakhontov, L. N.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1980.Related Products of 1122-71-0 This article mentions the following:

Reaction of 2,6-lutidine (I) with PhLi in ether with a 1:8 molar ratio of reagent at either room temperature or reflux did not give the dilithio derivatives but gave the monolithio derivatives I did not react with 2.5 mol Br in glacial HOAc at 80-100° without a catalyst or in the presence of ZnCl₂ or excess NaOAc. Chlorination of I did not take place at reflux with a 5-fold excess of SO₂Cl₂. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Related Products of 1122-71-0).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Related Products of 1122-71-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electrochemical PINOylation of Methylarenes: Improving the Scope and Utility of Benzylic Oxidation through Mediated Electrolysis was written by Hoque, Asmaul Md;Twilton, Jack;Zhu, Jieru;Graaf, Matthew D.;Harper, Kaid C.;Tuca, Emilian;DiLabio, Gino A.;Stahl, Shannon S.. And the article was included in Journal of the American Chemical Society in 2022.Name: (4-Chlorophenyl)methanol This article mentions the following:

A mediated electrosynthetic method has been developed for selective benzylic oxidation of methylarenes RCH₃ (R = Ph, 4-chlorophenyl, pyridin-3-yl, 1,3-thiazol-2-yl, etc.). Phthalimide-N-oxyl (PINO) radical generated by proton-coupled electrochem. oxidation of N-hydroxypthalimide serves as a hydrogen atom-transfer (HAT) mediator and as a radical trap for the benzylic radicals generated in situ. This mediated electrolysis method operates at much lower anode potentials relative to direct electrolysis methods for benzylic oxidation initiated by single-electron transfer (SET). A direct comparison of SET and mediated-HAT electrolysis methods with a common set of substrates shows that the HAT reaction exhibits a significantly improved substrate scope and functional group compatibility. The PINOylated products I and II are readily converted into the corresponding benzylic alc. RCH₂OH or benzaldehyde derivatives RCHO under photochem. conditions, and the synthetic utility of this method is highlighted by the late-stage functionalization of the non-steroidal anti-inflammatory drug celecoxib. In the experiment, the researchers used many compounds, for example, (4-Chlorophenyl)methanol (cas: 873-76-7Name: (4-Chlorophenyl)methanol).

(4-Chlorophenyl)methanol (cas: 873-76-7) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Name: (4-Chlorophenyl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts