Month: January 2023

Understanding Halide Counterion Effects in Enantioselective Ruthenium-Catalyzed Carbonyl (α-Aryl)allylation: Alkynes as Latent Allenes and Trifluoroethanol-Enhanced Turnover in The Conversion of Ethanol to Higher Alcohols via Hydrogen Auto-transfer was written by Ortiz, Eliezer;Shezaf, Jonathan Z.;Chang, Yu-Hsiang;Goncalves, Theo P.;Huang, Kuo-Wei;Krische, Michael J.. And the article was included in Journal of the American Chemical Society in 2021.SDS of cas: 142253-56-3 This article mentions the following:

Crystallog. characterization of RuX(CO)(η³-C₃H₅)(JOSIPHOS), where X = Cl, Br, or I, reveals a halide-dependent diastereomeric preference that defines metal-centered stereogenicity and, therefrom, the enantioselectivity of C-C coupling in ruthenium-catalyzed anti-diastereo- and enantioselective C-C couplings of primary alcs. with 1-aryl-1-propynes to form products of carbonyl anti-(α-aryl)allylation. Computational studies reveal that a non-classical hydrogen bond between iodide and the aldehyde formyl CH bond stabilizes the favored transition state for carbonyl addition An improved catalytic system enabling previously unattainable transformations was developed that employs an iodide-containing precatalyst, RuI(CO)₃(η³-C₃H₅), in combination with trifluoroethanol, as illustrated by the first enantioselective ruthenium-catalyzed C-C couplings of ethanol to form higher alcs. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3SDS of cas: 142253-56-3).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. 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.SDS of cas: 142253-56-3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Amino Acid Derived Chiral Aminobenzimidazole Manganese Catalysts for Asymmetric Transfer Hydrogenation of Ketones was written by Wang, Lixian;Lin, Jin;Sun, Qiangsheng;Xia, Chungu;Sun, Wei. And the article was included in ACS Catalysis in 2021.Quality Control of (S)-1-(2-Fluorophenyl)ethanol This article mentions the following:

A series of Mn(I) catalysts with chiral bidentate benzimidazoles derived from easily available amino acids has been developed. These types of phosphine-free chiral Mn catalysts demonstrate high activity and enantioselectivity in asym. transfer hydrogenation (ATH) for a broad range of ketone substrates. A bulkier substrate, such as 2,6-dichloro-3-fluoroacetophenone, can be converted into the drug intermediate alc. with up to 90% yield and 92% ee (e.g., crizotinib). On the basis of exptl. and DFT studies, a possible mechanism for this Mn-catalyzed ATH is also proposed. DFT calculations further render a plausible model for enantiocontrol in ketone hydrogenation, in which the π-π stacking interaction between the catalyst and the substrate plays an important role. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Quality Control of (S)-1-(2-Fluorophenyl)ethanol).

(S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4) 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.Quality Control of (S)-1-(2-Fluorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A family of immobilizable chiral bis(pinenebipyridine) ligands was written by Pollnitz, Alpar;Skupienski, Radek;Stoeckli-Evans, Helen;Crochet, Aurelien;Silvestru, Anca;Fromm, Katharina M.;Mamula, Olimpia. And the article was included in Synlett in 2013.Reference of 49669-14-9 This article mentions the following:

New enantiopure ligands I [RR¹ = O(CH₂)₂O; RR¹ = O; R = H, R¹ = OH] containing 2 (-)-5,6-pinenebipyridine units connected by a bridge situated in position 6′ of the bipyridines were prepared The chem. addressable groups of the bridge (hydroxyl or keto) can be covalently bound to various supports in order to heterogenize the ligand. In the experiment, the researchers used many compounds, for example, 2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine (cas: 49669-14-9Reference of 49669-14-9).

2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine (cas: 49669-14-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Reference of 49669-14-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Direct and Unified Access to Carbon Radicals from Aliphatic Alcohols by Cost-Efficient Titanium-Mediated Homolytic C-H Bond Cleavage was written by Suga, Takuya;Takahashi, Yuuki;Miki, Chinatsu;Ukaji, Yutaka. And the article was included in Angewandte Chemie, International Edition in 2022.Safety of 2-(4-(Trifluoromethyl)phenyl)ethanol This article mentions the following:

Low-valent Ti-mediated homolytic C-O bond cleavage offers unified access to carbon radicals from ubiquitous non-activated tertiary, secondary, and even primary alcs. In contrast to the representative Ti reagents, which were ineffective for this purpose, “TiCl₂(cat)”/Zn (cat=catecholate) was found to be specifically active. This method was applied to the addition reactions of radicals to alkenes and exhibited high generality and yields. More than 50 combinations were examined The excellent cost-efficiency and accessibility of “TiCl₂(cat)”/Zn further enhance its applicability. Control experiments proved the presence of a carbon radical intermediate and excluded the pathway via alkyl chlorides. Further mechanistic study indicated that the 1 : 2 complex of alkoxide (R-O-) and TiIII is an active species in the C-O cleavage. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Safety of 2-(4-(Trifluoromethyl)phenyl)ethanol).

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

The combined effect of protein hydrolysis and Lactobacillus plantarum fermentation on antioxidant activity and metabolomic profiles of quinoa beverage was written by Meng, Fan-Bing;Zhou, Li;Li, Jia-Jia;Li, Yun-Cheng;Wang, Meng;Zou, Long-Hua;Liu, Da-Yu;Chen, Wei-Jun. And the article was included in Food Research International in 2022.Formula: C18H32CaN2O10 This article mentions the following:

Lactic acid bacteria fermentation is a commonly applied technique to produce nutritional, functional, and organoleptic enhanced foods. In the present study, protein hydrolysis and Lactobacillus plantarum fermentation were coupled to develop quinoa beverages. Protein hydrolysis effectively promoted the growth and fermentation of L. plantarum. Fermentation alone did not significantly improve antioxidant activity, but the combined use of protein hydrolysis and L. plantarum fermentation significantly improved the antioxidant activity of the quinoa beverage. Nontargeted metabolomics based on UHPLC-Q Exactive HF-X/MS and multivariate statistical anal. were performed to reveal the metabolite profile alterations of the quinoa beverage by different processing methods. A total of 756 metabolites were identified and annotated, which could be categorized into 12 different classes. The significant differentially abundant metabolites were mainly involved in primary metabolite metabolism and secondary metabolite biosynthesis. Many of these metabolites were proven to be vitally important to the function and taste formation of the quinoa beverage. Most importantly, the coupled use of protein hydrolysis and L. plantarum fermentation significantly increased some functional ingredients compared with protein hydrolysis and L. plantarum fermentation alone. The above results indicate that protein hydrolysis coupled with L. plantarum fermentation is an effective strategy to develop functional quinoa beverages. In the experiment, the researchers used many compounds, for example, Calcium (R)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate (cas: 137-08-6Formula: C18H32CaN2O10).

Calcium (R)-3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoate (cas: 137-08-6) 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.Formula: C18H32CaN2O10

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Catalytic Zinc Complexes for Phosphate Diester Hydrolysis was written by Tirel, Emmanuel Y.;Bellamy, Zoe;Adams, Harry;Duarte, Fernanda;Williams, Nicholas H.. And the article was included in Angewandte Chemie, International Edition in 2014.Application of 1122-71-0 This article mentions the following:

Creating efficient artificial catalysts that can compete with biocatalysis has been an enduring challenge which has yet to be met. Reported herein is the synthesis and characterization of a series of zinc complexes designed to catalyze the hydrolysis of phosphate diesters. By introducing a hydrated aldehyde into the ligand we achieve turnover for DNA-like substrates which, combined with ligand methylation, increases reactivity by two orders of magnitude. In contrast to current orthodoxy and mechanistic explanations, we propose a mechanism where the nucleophile is not coordinated to the metal ion, but involves a tautomer with a more effective Lewis acid and more reactive nucleophile. This data suggests a new strategy for creating more efficient metal ion based catalysts, and highlights a possible mode of action for metalloenzymes. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0Application of 1122-71-0).

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. 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.Application of 1122-71-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate was written by Mineno, Tomoko. And the article was included in Tetrahedron Letters in 2002.Formula: C9H9F3O This article mentions the following:

Indium triflate-mediated tetrahydropyranylation of alcs. in CH₂Cl₂ and depyranylation of these products in aqueous MeOH using the same reagent but different molar ratio is described. Indium triflate-promoted conversion of tetrahydropyran ethers to their corresponding acetates also was described. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Formula: C9H9F3O).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. 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.Formula: C9H9F3O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Novel one-component polymeric benzophenone photoinitiator containing poly (ethylene glycol) as hydrogen donor was written by Wang, Kemin;Lu, Yuhui;Chen, Penghui;Shi, Jingsong;Wang, Hongning;Yu, Qiang. And the article was included in Materials Chemistry and Physics in 2014.Name: ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) This article mentions the following:

Benzophenone (BP) is a common initiator which is often used in the UV-curing production and related fields. However, the shortcomings such as toxicity, odor, and migration always limit the development of the traditional BP photoinitiator. Polymeric benzophenone photoinitiator (PEG-BP) was synthesized basing on polyethylene glycol (PEG), succinic anhydride, 4-hydroxybenzophenone and epichlorohydrin. The structure of PEG-BP was characterized by IR and ¹H NMR. The radiation absorption of PEG-BP was detected by UV spectrophotometer with the maximum absorption wavelength at 283 nm in acetonitrile solvent, undergone significant red shift corresponding to small mol. photoinitiator BP, thus enhanced the photosensitive efficiency of UV-curing system in the long wavelength region. Besides, PEG-BP has better water solubility than BP, thus could be used in both oil and aqueous solution The obvious advantage of this initiator was the elimination of amine based hydrogen donors and to provide alternative hydrogen donors with easily availability and non-toxicity. The effects of mol. weights of PEG-BP, photoinitiator concentration, UV-radiation intensity and different monomers on photopolymerization kinetics were investigated in detail. The synthesized polymeric photoinitiators are attractive to be used as type II photoinitiators. In the experiment, the researchers used many compounds, for example, ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) (cas: 109-17-1Name: ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate)).

((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) (cas: 109-17-1) 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. 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.Name: ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate)

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A Convenient Esterification of N-Heteroarene Methanols via C-CN Bond Cleavage of Benzoyl Cyanides as Acylating Sources was written by Su, Fangyao;Zhao, Qianrui;Wang, Mengzhuo;Zhao, Mingzhang;Ren, Yihe;Zhu, Binghan;Chen, Haoran;Lai, Miao;Zhao, Mingqin. And the article was included in ChemistrySelect in 2022.HPLC of Formula: 118289-16-0 This article mentions the following:

An efficient and straightforward methodol. for the esterification of various N-heteroarene methanols using benzoyl cyanides as acylating sources through a simply mixing conditions has been reported. The acyl groups were in-situ generated via chemoselective C-CN bond cleavage to give the N-heteroarenemethyl esters. This process features in readily accessible starting materials and offers an easy operational procedure, and broad substrate scope with excellent selectivity. In the experiment, the researchers used many compounds, for example, 2-Bromopyridine-4-methanol (cas: 118289-16-0HPLC of Formula: 118289-16-0).

2-Bromopyridine-4-methanol (cas: 118289-16-0) 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. 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.HPLC of Formula: 118289-16-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Effects of controlled atmosphere and storage temperature on the quality of shelled ‘Barton’ pecan nuts during long-term storage was written by Ribeiro, Stephanie Reis;Klein, Bruna;Santos, Ingrid Duarte dos;Thewes, Flavio Roberto;Brackmann, Auri;Both, Vanderlei;Wagner, Roger. And the article was included in Food Research International in 2022.Category: alcohols-buliding-blocks This article mentions the following:

This study aimed to evaluate the effects of controlled atm. (CA) storage at a low oxygen partial pressure (pO2; 2 kPa of O2) and low pO2 associated with high pCO2 (2 kPa O2 + 15 kPa CO2) in relation to ambient atm. conditions (control), at different temperatures, on shelled Barton pecan nuts quality after storage. Color, respiration rates, moisture content (MC), and oxidation markers, such as peroxide value (PV), acidity value (AV), and volatile compounds (VC), were evaluated. During six months of storage, the MC decreased in all CA treatments, and treatments at 10°C had the lowest AVs and PVs. However, the treatment with high pCO2 levels also guaranteed lower AVs at 20°C. The color parameter b* (yellow), which is related to the golden appearance of pecans and is a highly desirable visual attribute in the commercialization of nuts, was maintained high in treatments at 10°C with CA treatments until six months of storage. The VCs, characteristic of lipid oxidation (aldehydes, acids, alcs., and ketones), increase in all treatments with prolonging storage. When pCO2 was associated to 10°C at six month of storage, it showed a larger area in the acids and unsaturated aldehyde classes, while it was relevant for alcs., lactones, and esters at 20°C, with sweet characteristics, including Et ethanoate, Et hexanoate, and butyrolactone. Thus, this study shows another advance in the storage techniques of shelled pecans, pointing to alternatives for reducing energy costs in the cooling chain. In the experiment, the researchers used many compounds, for example, Oct-1-en-3-ol (cas: 3391-86-4Category: alcohols-buliding-blocks).

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. 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts