Month: February 2023

Chiral Bidentate Boryl Ligand-Enabled Iridium-Catalyzed Enantioselective Dual C-H Borylation of Ferrocenes: Reaction Development and Mechanistic Insights was written by Zou, Xiaoliang;Li, Yinwu;Ke, Zhuofeng;Xu, Senmiao. And the article was included in ACS Catalysis in 2022.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:

Ferrocenes with planar chirality are an important class of privileged scaffolds for diverse chiral ligands and organocatalysts. The development of efficient catalytic asym. methods under mild reaction conditions is a long-sought goal in this field. Though many transition-metal-catalyzed asym. C-H activation methods were recorded during the last decade, most of them are related to C-C bond-forming reactions. Owing to the useful attribute of the C-B bond, the authors herein report an amide-directed Ir-catalyzed enantioselective dual C-H borylation of ferrocenes. The key to the success of this transformation relies on a chiral bidentate boryl ligand and a judicious choice of a directing group. The current reaction could tolerate a vast array of functionalities, affording a variety of chiral borylated ferrocenes with good to excellent enantioselectivities (35 examples, up to 98% enantiomeric excess). The authors also demonstrated the synthetic utility by preparative-scale reaction and transformations of a borylated product. Finally, from the observed exptl. data, the authors performed DFT calculations to understand its reaction pathway and chiral induction, which reveals that Me C(sp³)-H borylation is crucial to conferring high enantioselectivity through an amplified steric effect caused by an interacted B-O fragment in the transition state. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) 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. Under carefully controlled conditions, simple alcohols can undergo intermolecular dehydration to give ethers. This reaction is effective only with methanol, ethanol, and other simple primary alcohols.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dual-stimuli-responsive glycopolymer bearing a reductive and photo-cleavable unit at block junction was written by Fang, Jia-You;Lin, Yin-Ku;Wang, Shiu-Wei;Yu, Yung-Ching;Lee, Ren-Shen. And the article was included in RSC Advances in 2016.Computed Properties of C7H7NO4 This article mentions the following:

New dual-stimuli-responsive and bio-recognizable glycopolymers (Glyco-ONB-s-s-PXCL) containing a photodegradable 5-hydroxy-2-nitrobenzyl alc. (ONB), and a redox-cleavable disulfide (-s-s-) as junction point between bio-recognizable hydrophilic sugar mol. (Glyco) and hydrophobic poly(4-substituted ε-caprolactone) (PXCL) chains were synthesized using a combination of ring-opening polymerization and nucleophilic substitution reactions. When the polymer solution was exposed to UV irradiation and/or the reducing agent DL-dithiothreitol (DTT), substantial structural and morphol. changes were observed in the particles. The polymers formed micelles in the aqueous solution, had hydrodynamic sizes ≤200 nm, and were spherical. Under the combined stimulation of UV irradiation and DTT, the micellar nanoparticles dissociated and the loaded mols. could be released from the assemblies more efficiently than under the stimulation of only one of the two stimuli. Selective lectin binding experiments confirmed that glucosylated Gluco-ONB-s-s-PXCL can be used for bio-recognition. The nanoparticles exhibited nonsignificant toxicity against HeLa cells at concentrations of ≤300 μg mL^-1. The DOX-loaded Gluco-ONB-s-s-PMCL₂₀ micelles effectively inhibited the proliferation of HeLa cells with a half-maximal inhibitory concentration (IC₅₀) of 1.5 μg mL^-1. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Computed Properties of C7H7NO4).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Computed Properties of C7H7NO4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A new catalytic approach for aerobic oxidation of primary alcohols based on a Copper(I)-thiophene carbaldimines was written by Lagerspets, Emi;Valbonetti, Evelyn;Eronen, Aleksi;Repo, Timo. And the article was included in Molecular Catalysis in 2021.Related Products of 1777-82-8 This article mentions the following:

Novel Cu(I) thiophene carbaldimine catalysts for the selective aerobic oxidation of primary alcs. to their corresponding aldehydes and various diols to lactones or lactols was reported. In the presence of the in-situ generated Cu(I) species, a persistent radical (2,2,6,6-tetramethylpiperdine-N-oxyl (TEMPO)) and N-methylimidazole (NMI) as an auxiliary ligand, the reaction proceeds under aerobic conditions and at ambient temperature Especially the catalytic system of 1-(thiophen-2-yl)-N-(4-(trifluoromethoxy)phenyl)methanimine with copper(I)-iodide showed high reactivity for all kind of alcs. (benzylic, allylic and aliphatic). In the case of benzyl alc. even 2.5 mol% of copper loading gave quant. yield. Beside high activity under aerobic conditions, the catalysts ability to oxidize 1,5-pentadiol to the corresponding lactol (86% in 4 h) and N-phenyldiethanolamine to the corresponding morpholine derivate lactol (86% in 24 h) is particularly noteworthy. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Related Products of 1777-82-8).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) 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 1777-82-8

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Comprehensive investigation on non-volatile and volatile metabolites in four types of green teas obtained from the same tea cultivar of Longjing 43 (Camellia sinensis var. sinensis) using the widely targeted metabolomics was written by Shi, Yali;Zhu, Yin;Ma, Wanjun;Shi, Jiang;Peng, Qunhua;Lin, Zhi;Lv, Haipeng. And the article was included in Food Chemistry in 2022.Computed Properties of C8H16O This article mentions the following:

In this study, we produced roasted, baked, steamed, and sun-dried green tea products using the same batch of fresh tea leaves (FTL) of Longjing 43 (Camellia sinensis var. sinensis), and explored processing effects on the metabolic profiles of four types of green teas (FGTs) using the widely targeted metabolomics. Results showed that 146 differential metabolites including flavonoids, amino acids, lipids, and phenolic acids were screened among 1034 non-volatiles. In addition, nineteen differential metabolites were screened among 79 volatiles. Most of non-volatiles and volatiles metabolites changed notably in different manufacturing processes, whereas there were no significant differences (p>0.05) in the levels of total catechins between FGTs and FTL. The transformation of metabolites was the dominant trend during green tea processing. The results contribute to a better understanding of how the manufacturing process influences green tea quality, and provide useful information for the enrichment of tea biochem. theory. In the experiment, the researchers used many compounds, for example, Oct-1-en-3-ol (cas: 3391-86-4Computed Properties of C8H16O).

Oct-1-en-3-ol (cas: 3391-86-4) 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. 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.Computed Properties of C8H16O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dietary exposure to low-calorie sweeteners in a sample of Brazilian pregnant women was written by Duarte, Larissa Marinho;Ferreira, Sila Mary Rodrigues;Almeida, Claudia Choma Bettega;Duran, Ana Clara da Fonseca Leitao;Grilo, Mariana Fagundes;Macedo, Mariana de Souza;Franceschini, Sylvia do Carmo Castro;Crispim, Sandra Patricia. And the article was included in Food Additives & Contaminants, Part A in 2022.Safety of (2R,3S)-rel-Butane-1,2,3,4-tetraol This article mentions the following:

The dietary exposure to low-calorie sweeteners (LCS) was estimated in a sample of pregnant Brazilian women. Consumption data were obtained with a 24-h Dietary Recall interview. Because of the uncertainty in assessing foods with LCS, they were classified into three scenarios to ensure inclusion of the 15 LCS allowed for use in Brazil: ranging from a less to a more conservative scenario. The concentration of LCS was estimated using the amount declared on the label or the maximum permitted levels and anal. determination data for table-top sweeteners. The frequency of consumption was higher for acesulfame-K, aspartame, and cyclamate. The food groups contributing the most to the consumption of LCS were non-alc. beverages, table-top sweeteners, confectionary and desserts. The level of dietary exposure to LCS was within the safety limit. However, continued efforts to monitor their dietary exposure are necessary given the limitations highlighted in this study. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Safety of (2R,3S)-rel-Butane-1,2,3,4-tetraol).

(2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6) 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. 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.Safety of (2R,3S)-rel-Butane-1,2,3,4-tetraol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Identification and characterization of chemical and physical stability of insulin formulations utilizing degraded glycerol after repeated use and storage was written by Sun, Min-Fei;Xu, Youfu;Yuan, Jun-Jie;Fang, Wei-Jie. And the article was included in European Journal of Pharmaceutics and Biopharmaceutics in 2022.Quality Control of 1,2-Propanediol This article mentions the following:

Insulin treatment is currently considered to be the main strategy for controlling diabetes. Although the recombinant insulin formulation is relatively mature, we found that a batch of insulin formulation exhibited an unusual degradation rate in the stability experiment The main purposes of this article are to identify the root cause for this phenomenon and characterize of chem. and phys. degradation products. We compared the chem. and phys. stability of two batches of insulin formulations prepared sep. with simulated repeated use and freshly opened glycerol. The chem. stability of insulin was identified by liquid chromatog. coupled with tandem mass spectrometry (LC- MS/MS). Micro-flow imaging (MFI), far-UV CD (Far-UV CD) and Thioflavin T (ThT) fluorescent assays were used to reveal protein aggregation and fibrosis. The chem. and phys. stability of the insulin formulation with newly opened glycerol was much better than that with degraded glycerol, and both groups of formulations were extremely sensitive to light. The results indicated that the original batch insulin formulation with abnormal stability was indeed caused by the excipient glycerol after long-term storage and repeated usage. More attention should be paid to the quality changes of excipients during repeated usage and storage of excipients for the practical purpose. Moreover, we have discovered a novel degradation pathway for insulin and peptides in general. In addition, LC-MS/MS results suggested that the N-terminus of insulin B-chain was prone to chem. degradation which enlightens that it could be potentially modified to improve the stability of insulin formulations. 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

Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO₂: Facile Synthesis of Diacids and Derivatization into Polyesters was written by Liao, Li-Li;Wang, Zhe-Hao;Cao, Ke-Gong;Sun, Guo-Quan;Zhang, Wei;Ran, Chuan-Kun;Li, Yiwen;Chen, Li;Cao, Guang-Mei;Yu, Da-Gang. And the article was included in Journal of the American Chemical Society in 2022.Recommanded Product: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:

A novel electrochem. ring-opening dicarboxylation of C-C single bonds in strained rings with CO₂ was reported. Structurally diverse glutaric acid and adipic acid derivatives HO(O)CC(Ar¹)R(CH₂)_nCH(Ar²)C(O)OH (R = H, Me, Ph; Ar¹ = Ph, 3-methylphenyl, 2,3-dihydro-1-benzofuran-6-yl, etc.; n = 1, 2; Ar² = Ph, 4-fluorohenyl, 3-methylphenyl) and HO(O)CC(R¹)(R²)CH₂CH(C(O)OR³)C(O)OH [R¹ = H, Me, Ph; R² = 4-tert-butylphenyl, C(O)OEt, 4-chlorophenyl, etc.; R³ = Et, (2S,5S)-5-methyl-2-(propan-2-yl)cyclohexyl, Ph, etc.] are synthesized from substituted cyclopropanes I, II and cyclobutanes III in moderate-to-high yields. In contrast to oxidative ring openings, it is also the first time to realize electro-reductive ring-opening reaction of strained rings, including commercialized ones. Control experiments suggest that radical anions and carbanions might be the key intermediates in this reaction. Moreover, this process features high step and atom economy, mild reaction conditions (1 atm, room temperature), good chemoselectivity and functional group tolerance, low electrolyte concentration, and easy derivatization of products. Furthermore, the polymerization of the corresponding diesters with diols is conducted to obtain a potential UV-shielding material with self-healing function and a fluorine-containing polyester, whose performance tests show a promising application. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Recommanded Product: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) 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. 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.Recommanded Product: (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Scandium Triflate Catalyzed Tandem Transfer Hydrogenation and Cyclization Reaction of o-Aminobenzaldehydes and o-Aminoacetophenone with Alcohols was written by Gou, Bo-Bo;Yang, Sen;Sun, Huai-Ri;Jian, Qing-Song;Sharif, Atif;Zhou, Ling;Chen, Jie. And the article was included in Journal of Organic Chemistry in 2021.Quality Control of 2-(4-(Trifluoromethyl)phenyl)ethanol This article mentions the following:

An effective Sc-catalyzed transfer hydrogenation and cyclization tandem reaction has been achieved. This process showed excellent functional group compatibility and good yields. A variety of benzoxazines I (R = H, Me; R¹ = H, Me, Et; R² = Me, Ph, naphthalen-1-yl, thiophen-2-ylmethyl, etc.; R¹R² = -(CH₂)₅-; R³ = H, F, Cl, Me, Br; R⁴ = H, Me; R⁵ = H, Me, Cl, Br) were produced with primary or secondary alcs. R²(R³)CH₂OH as a hydrogen source. Furthermore, the utility of this newly developed protocol is demonstrated through scaled-up experiment, late-stage modification, and preliminary exploration of enantioselective synthesis. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Quality Control of 2-(4-(Trifluoromethyl)phenyl)ethanol).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) 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. 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.Quality Control of 2-(4-(Trifluoromethyl)phenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Paired electrolysis enabled annulation for the quinolyl-modification of bioactive molecules was written by You, Shiqi;Ruan, Mengyao;Lu, Cuifen;Liu, Li;Weng, Yue;Yang, Guichun;Wang, Shengchun;Alhumade, Hesham;Lei, Aiwen;Gao, Meng. And the article was included in Chemical Science in 2022.Synthetic Route of C24H23ClO2 This article mentions the following:

A paired electrolysis enabled cascade annulation that enables the efficient synthesis of highly functionalized quinoline-substituted bioactive mols. from readily available starting materials is reported. Using this methodol., two goals, namely, the direct synthesis of quinolines and the introduction of quinoline moieties to bioactive mols., can be simultaneously achieved in one simple operation. The use of electroreduction for the activation of isatin, together with the further anodic oxidation of KI to catalytically result in a cascade annulation, highlight the unique possibilities associated with electrochem. activation methods. This transformation can tolerate a wide range of functional groups and can also be used as a functionalization tactic in pharmaceutical research as well as other areas. In the experiment, the researchers used many compounds, for example, (Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7Synthetic Route of C24H23ClO2).

(Z)-2-(4-(4-Chloro-1,2-diphenylbut-1-en-1-yl)phenoxy)ethan-1-ol (cas: 128607-22-7) 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. 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.Synthetic Route of C24H23ClO2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Suspect screening of emerging pollutants and their major transformation products in wastewaters treated with fungi by liquid chromatography coupled to a high resolution mass spectrometry was written by Llorca, Marta;Lucas, Daniel;Ferrando-Climent, Laura;Badia-Fabregat, Marina;Cruz-Morato, Carles;Barcelo, Damia;Rodriguez-Mozaz, Sara. And the article was included in Journal of Chromatography A in 2016.Formula: C16H16O3 This article mentions the following:

A new approach for the screening of 33 pharmaceuticals and 113 of their known transformation products in wastewaters is based on the anal. of samples by liquid chromatog. coupled to high resolution mass spectrometry (HRMS) followed by data processing using specific software and manual confirmation. A home-made library was built with the transformation products reported in literature for the target pharmaceuticals after treatment with various fungi. The method was applied to the search of these contaminants in 67 samples generated along treatment of wastewaters with white-rot fungus Trametes versicolor. The screening methodol. allowed the detection of different transformation products (TPs) generated from degradation of parent compounds after fungal treatment. This approach can be a useful tool for the rapid screening and tentative detection of emerging contaminants during water treatment in both full and batch-scale studies when pure standards are not available. In the experiment, the researchers used many compounds, for example, 2-(3-(Hydroxy(phenyl)methyl)phenyl)propanoic acid (cas: 59960-32-6Formula: C16H16O3).

2-(3-(Hydroxy(phenyl)methyl)phenyl)propanoic acid (cas: 59960-32-6) 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.Formula: C16H16O3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts