Tag: 100-200

Efficient synthesis of 2,6-bis(hydroxymethyl)pyridine using whole-cell biocatalysis was written by Kardashliev, Tsvetan;Panke, Sven;Held, Martin. And the article was included in Green Chemistry in 2022.Synthetic Route of C7H9NO This article mentions the following:

We demonstrate a novel one-pot biocatalytic process for the preparation of a versatile chem. intermediate, 2,6-bis(hydroxymethyl)pyridine, from naturally-occurring 2,6-lutidine using recombinant microbial whole cells as a catalysts. After scale up, the bioconversion enabled titers exceeding 12 g L^-1 with a space-time yield of 0.8 g L^-1 h^-1. This biocatalytic route offers a simpler and more sustainable alternative to multistep organic synthesis protocols. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Synthetic Route of C7H9NO).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) 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 C7H9NO

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ortho-Formylation of oxygenated phenols was written by Akselsen, Oyvind W.;Skattebol, Lars;Hansen, Trond Vidar. And the article was included in Tetrahedron Letters in 2009.SDS of cas: 69393-72-2 This article mentions the following:

Oxygenated phenols are mono-formylated using a mixture of (CH₂O)_n, MgCl₂, and Et₃N in THF. In all cases but one, only one regioisomer of the salicylaldehyde is obtained in good to high yield. In the experiment, the researchers used many compounds, for example, Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2SDS of cas: 69393-72-2).

Benzo[d][1,3]dioxol-4-ol (cas: 69393-72-2) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.SDS of cas: 69393-72-2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Temperature-pressure correlations of cryoprotective additives for the design of constant volume cryopreservation protocols was written by Beschea, George-Andrei;Tabacaru, Maria-Bianca;Campean, Stefan-Ioan;Serban, Alexandru;Vutoiu, Beatrice-Georgiana;Stefanescu, Mariana-Florentina;Dobrovicescu, Alexandru;Nastase, Gabriel. And the article was included in Cryobiology in 2022.Formula: C4H10O3 This article mentions the following:

In the recent years, the use of constant volume (isochoric) cryopreservation, in medicine and biotechnol. has captured more attention from the research community and now there is an increasing interest in the use of this new technol. It has been established that the thermodn. of isochoric freezing is different from that of isobaric (constant pressure) freezing. This study provides researchers in the field exptl. results for various compositions of cryoprotectants commonly used in isobaric cryopreservation, in terms of temperature-pressure-molar concentration correlation. It also reveals exptl. isochoric thermodn. data for the following cryoprotectants, commonly used in isobaric cryopreservation: DMSO, trehalose, ethylene glycol and diethylene glycol. Currently, the data on the pressure-temperature correlation in an isochoric system of cryoprotectants used in isobaric cryopreservation is not available. Our new exptl. results indicate that the studied concentrations for each of the CPAs, lower and expands the range of temperatures in which cryopreservation by isochoric freezing can be safely practiced. We consider that these experiments will aid researchers developing new isochoric cryopreservation protocols. In the experiment, the researchers used many compounds, for example, 2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6Formula: C4H10O3).

2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6) 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. 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.Formula: C4H10O3

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Alcohol – Wikipedia,
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Enhancing phosphate diester cleavage by a zinc complex through controlling nucleophile coordination was written by Tirel, Emmanuel Y.;Williams, Nicholas H.. And the article was included in Chemistry – A European Journal in 2015.Electric Literature of C7H9NO This article mentions the following:

Metal-ion complexes are the most effective artificial catalysts capable of cleaving phosphate diesters under mild aqueous conditions. A central strategy for making these complexes highly reactive has been to use ligand-based alcs. that are coordinated to the ion, providing an ionized nucleophile under neutral conditions but at the expense of deactivating it. We have created a highly reactive Zn complex that is 350-fold more reactive than an alc. analog by preventing the nucleophile binding to the metal ion. This strategy successfully delivers the benefits of efficient nucleophile delivery without strongly deactivating the metal ion Lewis acidity nor the oxyanion nucleophilicity. Varying the leaving group reveals that the transition state of the reaction is much further advanced than the reaction with hydroxide. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Electric Literature of C7H9NO).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Electric Literature of C7H9NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Metabolism of fenitrothion in birds was written by Mihara, Kazumasa;Misaki, Yoshinori;Miyamoto, Junshi. And the article was included in Nippon Noyaku Gakkaishi in 1979.Reference of 60463-12-9 This article mentions the following:

Within 24 h after oral administration of ¹⁴C-labeled fenitrothion (I) [122-14-5] to female Japanese quails singly at 5 mg/kg or to White Leghorn hens for 7 days at 2 mg/kg/day, 97-99% of the applied ¹⁴C was excreted without accumulation of ¹⁴C in any tissue. At most 0.2% of the applied ¹⁴C was eliminated into eggs. Of >18 metabolites in the excreta, 14 were identified. The quails and hens excreted 70.5 and 50.8%, resp., of the applied ¹⁴C as 3-methyl-4-nitrophenol [2581-34-2] including its sulfate [60463-13-0]. Only 10-15% of the applied ¹⁴C was excreted as O-demthylation product of I [4321-64-6] and fenitrooxon (II) [2255-17-6], whereas 13-18% was excreted as 3-hydroxymethyl-4-nitrophenol [60463-12-9] and β-glucuronide [72041-46-4]. Hen, pheasant, and quail liver enzyme preparations had higher activities of oxidizing II to dimethyl 3-hydroxymethyl-4-nitrophenyl phosphate [66558-68-7] than those of mammals, but had much lower activities of demethylating I at the P-O-Me linkage. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9Reference of 60463-12-9).

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. 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.Reference of 60463-12-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The effect of fluorine substitution on chiral recognition: interplay of CH···π, OH···π and CH···F interactions in gas-phase complexes of 1-aryl-1-ethanol with butan-2-ol was written by Ciavardini, Alessandra;Rondino, Flaminia;Paladini, Alessandra;Speranza, Maurizio;Fornarini, Simonetta;Satta, Mauro;Piccirillo, Susanna. And the article was included in Physical Chemistry Chemical Physics in 2013.Recommanded Product: 171032-87-4 This article mentions the following:

The mol. diastereomeric complexes between R-1-phenyl-1-ethanol, S-1-(4-fluorophenyl)ethanol and S-1-(2-fluorophenyl)ethanol and R and S-butan-2-ol, isolated under mol. beam conditions in the gas phase, were studied by mass-selective resonant two-photon ionization (R2PI) and IR depleted R2PI (IR-R2PI). The comparison of the three systems allowed the authors to highlight the significance of specific intermol. interactions in the chiral discrimination process. The interpretation of the results is based on theor. predictions mainly at the D-B3LYP/6-31++G^** level of theory. The homo and heterochiral complexes are endowed with fine differences in intermol. interactions, strong OH···O, and weaker CH···π, OH···π, CH···F as well as repulsive interactions. The presence of a fluorine atom in the para position of the aromatic ring does not influence the overall geometry of the complex while it affects the electron d. in the π system and the strength of CH···π and OH···π interactions. The role and the importance of CH···F intermol. interactions are evident in the complexes with fluorine substitution in the ortho position. While the ortho hetero complex is structurally analogous to the hetero para and nonfluorinated structures, butan-2-ol in the ortho homo adduct adopts a different conformation to establish a CH···F intermol. interaction. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Recommanded Product: 171032-87-4).

(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) 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.Recommanded Product: 171032-87-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Defluorinative Alkylation of Trifluoromethyl Alkenes with Soft Carbon Nucleophiles Enabled by a Catalytic Amount of Base was written by Gao, Ya;Qin, Wei;Tian, Ming-Qing;Zhao, Xuefei;Hu, Xu-Hong. And the article was included in Advanced Synthesis & Catalysis in 2022.Electric Literature of C10H20O This article mentions the following:

Direct manipulation of readily accessible trifluoromethyl alkenes (TAs) represents an attractive approach to the preparation of diversified fluorine-containing compounds In this study, defluorinative alkylation reactions of TAs with a broad array of soft carbon nucleophiles have been documented. Nucleophilic substitutions occur enabled by a catalytic amount of base, providing access to tertiary alkyl substituted gem-difluoroalkenes and 2-fluoro-4H-pyrans. By extending the nucleophiles to silyl enol ethers, defluorination can be achieved in the absence of base to give gem-difluoroalkenes. This process, which eliminates the requirement of organometallic reagents, transition metals, or strong bases for the C-F bond cleavage, is applicable to late-stage modification of complex mols. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Electric Literature of C10H20O).

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5) 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.Electric Literature of C10H20O

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Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Diverse synthesis of C2-linked functionalized molecules via molecular glue strategy with acetylene was written by Yang, Bo;Lu, Shaodong;Wang, Yongdong;Zhu, Shifa. And the article was included in Nature Communications in 2022.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:

A photoredox-catalyzed synthetic protocol for diverse C2-linked mols. via a mol. glue strategy using gaseous acetylene under mild conditions was developed. Initiated by addition of an acyl radical to acetylene, two cascade transformations follow. One involved a double addition for the formation of 1,4-diketones and the other where the intermediate vinyl ketone was intercepted by a radical formed from a heterocycle. In addition to making two new C-C bonds, two C-H bonds was also created in two mechanistically distinct ways: one via a C-H abstraction and the other via protonation. This system offered a reliable and safe way to incorporate gaseous acetylene into fine chems. and expanded the utility of acetylene in organic synthesis. 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. 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

o-Cyanobenzoate: A Recyclable and Reusable Stereo-directing Group for β-O-Glycosylation via Pd(0)-catalyzed Ferrier Rearrangement was written by Das, Pradip;Rahaman Molla, Mosidur;Kumar, Amit;Thakur, Rima. And the article was included in Chemistry – An Asian Journal in 2022.Reference of 2216-51-5 This article mentions the following:

Inner sphere Tsuji-Trost reaction has found recent application for β-selective Ferrier rearrangement of glycal substrates with alc. nucleophiles. Herein, we report an efficient and stereoselective synthesis of 2,3-dideoxy-β-O-glycosides from C3-(o-cyanobenzoate) ester protected glycal donors via Ferrier rearrangement under Pd(0)-catalyzed Tsuji-Trost conditions. The synthesized donors indeed reacted with a variety of acceptors to afford the corresponding glycosides in good yields and excellent β-stereoselectivity. The stereochem. outcome of the reactions has been found to be independent of the nature of protecting groups or conformational flexibility of the glycal donors. Furthermore, regeneration of ortho-cyanobenzoic acid post rearrangement makes it a recyclable and reusable stereo-directing group. A preliminary mechanistic study demonstrates the importance of cyano-group for the observed rearrangement and stereoselectivity. Incorporation of the directing group on the benzoate ester has altered the reactivity of the ester group as a leaving group for Tsuji-Trost as well as Ferrier Rearrangement pathway. In the experiment, the researchers used many compounds, for example, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol (cas: 2216-51-5Reference of 2216-51-5).

(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. 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.Reference of 2216-51-5

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Volatility parameterization of ambient organic aerosols at a rural site of the North China Plain was written by Ren, Siman;Yao, Lei;Wang, Yuwei;Yang, Gan;Liu, Yiliang;Li, Yueyang;Lu, Yiqun;Wang, Lihong;Wang, Lin. And the article was included in Atmospheric Chemistry and Physics in 2022.Application In Synthesis of (2R,3S)-rel-Butane-1,2,3,4-tetraol This article mentions the following:

The volatility of organic aerosols plays a key role in determining their gas-particle partitioning, which subsequently alters the physicochem. properties and atm. fates of aerosol particles. Nevertheless, an accurate estimation of the volatility of organic aerosols (OAs) remains challenging because most standards for particulate organic compounds are not available, and even for those with standards, their vapor pressures are too low to be measured by most traditional methods. Here, we deployed an iodide-adduct long time-of-flight chem. ionization mass spectrometer (LToF-CIMS) coupled with a Filter Inlet for Gases and AEROsols (FIGAERO) to probe the relationship between the mol. formulas of atm. organic aerosols’ components and their volatilities. T_max (i.e., the temperature corresponding to the first signal peak of thermogram) for calibrants was abstracted and validated from the desorption thermograms of mixed organic and inorganic calibrants that were atomized and then collected on a PTFE filter, leading to a linear correlation between T_max and volatility. In addition, 30 ambient filter samples were collected in winter 2019 at Wangdu station in the Beijing-Tianjin-Hebei region and analyzed by FIGAERO-LToF-CIMS, leading to the identification of 1448 compounds dominated by the CHO (containing carbon, hydrogen, and oxygen atoms) and CHON (containing carbon, hydrogen, oxygen, and nitrogen atoms) species. Among them, 181 organic formulas including 91 CHO and 90 CHON compounds were then selected since their thermograms can be characterized with clear T_max values in more than 20 out of 30 filter samples and subsequently divided into two groups according to their O / C ratios and different thermal desorption behavior. The mean O / C of these two groups is 0.56 ± 0.35 (average ± 1 standard deviation) and 0.18 ± 0.08, resp. Then the parameterizations between volatility and elemental composition for the two group compounds were obtained. Compared with previous volatility parameterizations, our functions provide a better estimation for the volatility of low-volatility organic compounds (LVOCs) in ambient organic aerosols. Furthermore, our results suggest that volatility parameterizations should be specialized for organic compounds with different O / C ratios. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Application In Synthesis 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Application In Synthesis of (2R,3S)-rel-Butane-1,2,3,4-tetraol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts