Month: January 2023

Synthesis and application of bulky phosphoramidites: highly effective monophosphorus ligands for asymmetric hydrosilylation of styrenes was written by Zhang, Feng;Fan, Qing-Hua. And the article was included in Organic & Biomolecular Chemistry in 2009.Safety of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol This article mentions the following:

A series of bulky monodentate phosphoramidite ligands were synthesized from chiral 3,3′-diaryl substituted BINOL derivatives and achiral or dendritic amines in good yields. Asym. hydrosilylation of styrenes with trichlorosilane in the presence of palladium complexes of these bulky ligands gave chiral silanes in high yields with excellent activity and productivity. Oxidation of these chiral silanes with hydrogen peroxide gave the corresponding chiral secondary alcs. in up to 96% ee. In the experiment, the researchers used many compounds, for example, (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6Safety of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol).

(S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6) 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.Safety of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Anchored [RuCl₂(p-cymene)]₂ in hybrid zirconium phosphate-phosphonate coated and pillared with double-stranded hydrophobic linear polystyrene as heterogeneous catalyst suitable for aqueous asymmetric transfer hydrogenation was written by Wang, Rui;Wan, Jingwei;Ma, Xuebing;Xu, Xiao;Liu, Liu. And the article was included in Dalton Transactions in 2013.Electric Literature of C8H9ClO This article mentions the following:

A novel type of phosphonate-containing polystyrene copolymers 1a-e bearing an N’-alkylated TsDPEN chiral ligand and double-stranded polystyrene chains were prepared for the first time using simple radical copolymerization of 1-phosphonate styrene with (R,R)-N’-4′-vinylbenzyl-N-4-vinylbenzenesulfonyl-1,2-diphenylethylene-1,2-diamine. Through the coprecipitation of their supported Ru polystyrene copolymers 2a-e and NaH₂PO₄ with ZrOCl₂, pillared hybrid zirconium phosphate-phosphonate-anchored Ru catalysts 3a-e and 4d₁-d₅ were obtained as heterogeneous catalysts suitable for aqueous asym. transfer hydrogenation. In the aqueous asym. transfer hydrogenation of aromatic ketones, the anchored Ru catalysts showed good catalytic activities, chemoselectivities (∼100%), and enantioselectivities (73.6% ee to 95.6% ee). The Ru catalysts retained their catalytic properties even at the fifth recycle time (92.2% conv., 92.1% ee). However, corresponding supported Ru catalyst 3d’ resulted in disappointing reusability because of the loss of ruthenium in every recycle process. The conversions of aromatic ketones were closely related to the o-, m- or p-positions of the substituents on the aromatic ring caused by shape-selective matching. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Electric Literature of C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. 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.Electric Literature of C8H9ClO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nickel-Catalyzed Intermolecular Carbobromination of Alkynes was written by Takahashi, Toshifumi;Kurahashi, Takuya;Matsubara, Seijiro. And the article was included in ACS Catalysis in 2020.Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane This article mentions the following:

The nickel-catalyzed intermol. carbobrominations of alkynes with aryl bromides to form highly substituted and functionalized alkenyl bromides such as I [R¹ = n-Pr, n-pentyl, Bu; R² = n-Pr, n-pentyl, Br; R¹R² = (CH₂)₁₀, (CH₂)₁₃; Ar = 2-MeC₆H₄, 4-MeCOC₆H₄, 1-anthracenyl, etc.]. The reductive elimination of carbon-bromine bond from a Ni(II) species, which was usually a disfavored process, was achieved from a high-valent Ni(III) species in this reaction. This transformation not only expands the scope of transition-metal-complex-promoted bond-forming reactions but also, more particularly, accomplished the formation of labile bonds, which was as challenging to achieve as the cleavage of inert bonds, such as C-O or C-H bonds. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) 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. 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.Name: 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Redox-driven deracemization of secondary alcohols by sequential ether/O₂-mediated oxidation and Ru-catalyzed asymmetric reduction was written by Yang, Bing;Cui, Peng;Chen, Yongsheng;Liu, Qixing;Zhou, Haifeng. And the article was included in Tetrahedron Letters in 2020.Safety of (S)-1-(2-Fluorophenyl)ethanol This article mentions the following:

The deracemization of secondary alcs. had been achieved using a redox-driven one-pot two-step process. The racemic alcs. were oxidized by bis(methoxypropyl) ether and oxygen to gave the ketone intermediates, followed by an asym. transfer hydrogenation with a chiral ruthenium catalyst. This compatible oxidation/reduction process gave the enantiomerically enriched alcs. such as RCH(OH)R¹ [R = Ph, 2-FC₆H₄, 3-thienyl, etc.; R¹ = Me, pentyl, CO₂Me, Ph] with up to 95% ee values. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Safety of (S)-1-(2-Fluorophenyl)ethanol).

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Laser-induced sound pinging for the rapid determination of total sugar or sweetener content in commercial beverages was written by Bhawawet, Nakara;Larm, Nathaniel E.;Adhikari, Laxmi;Polo-Parada, Luis;Gutierrez-Juarez, Gerardo;Baker, Gary A.. And the article was included in Talanta in 2022.Category: alcohols-buliding-blocks This article mentions the following:

We recently reported on fixed-path length laser-induced sound pinging (FPL-LISP) as a rapid photoacoustic technique employing an inexpensive benchtop tattoo-removal laser for reliably determining the speed of sound in low-volume fluids. In this contribution, we demonstrate the capacity of FPL-LISP to analyze representative com. beverages for their natural or artificial sweetener contents. As a benchmark, the speed of sound was determined for solutions of sugars (glucose, fructose, sucrose), mock high fructose corn syrup (HFCS-55), and 12 household sweeteners (culinary sugars, syrups, honey, molasses) across the concentration range of 1-20% w/v in water, simulating the typical sweetener range found in com. soft drinks. The setup was then employed to estimate sweetener contents of 26 popular com. beverages using the HFCS-55 standard curve as a training data set. Our results are remarkably consistent with the label values for these representative com. beverages, in spite of the fact that some beverages clearly employ a sweetener other than HFCS-55 or a proprietary blend, suggesting the excellent potential of the FPL-LISP setup as a quick screening tool well-suited to quality control and real-time assessment in the beverage and fermentation industrial sectors. The proposed approach represents a significant improvement over many existing methods on the basis of measurement time (down to 1 s, which can be considered real time for many applications), lenient sample requirements (tens of microliters to 1 mL), robust and user-friendly anal., practical considerations (e.g., economical, minimal service and maintenance concerns), and prospects for advancing both online monitoring and fully portable versions of this instrumentation. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Category: alcohols-buliding-blocks).

(2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6) 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.Category: alcohols-buliding-blocks

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthesis of N-heteroarenemethyl esters via C-C bond cleavage of acyl cyanides under transition metal-free conditions was written by Lai, Miao;Su, Fangyao;Hu, Jingyi;Wang, Mengzhuo;Zhao, Mingqin;Zhang, Ganlin. And the article was included in Frontiers in Chemistry (Lausanne, Switzerland) in 2021.SDS of cas: 1122-71-0 This article mentions the following:

A practical method to synthesize N-heteroaryl esters from N-heteroaryl methanols with acyl cyanides via C-C bond cleavage without using any transition metal is demonstrated here. The use of Na₂CO₃/15-crown-5 couple enables access to a series of N-heteroaryl esters in high efficiency. This protocol is operationally simple and highly environmentally benign producing only cyanides as byproducts. In the experiment, the researchers used many compounds, for example, 6-Methyl-2-pyridinemethanol (cas: 1122-71-0SDS of cas: 1122-71-0).

6-Methyl-2-pyridinemethanol (cas: 1122-71-0) 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. 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.SDS of cas: 1122-71-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Liquid chromatographic resolution of 1,1′-bi-2-naphthol and 3,3′-diaryl-1,1′-bi-2-naphthols on Pirkle-type chiral stationary phases based on leucine and phenylglycine was written by Hyun, Myung Ho;Kim, Kwang Soo;Cho, Yoon Jae. And the article was included in Journal of Liquid Chromatography & Related Technologies in 2005.Application In Synthesis of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol This article mentions the following:

Pirkle-type chiral stationary phases (CSPs) based on (S)-leucine and (S)-phenylglycine were applied in the resolution of 1,1′-bi-2-naphthol and 3,3′-diaryl-1,1′-bi-2-naphthols. Among the two Pirkle-type CSPs, the one based on (S)-N-(3,5-dinitrobenzoyl)leucine N-propylamide is excellent and most widely applicable. The elution orders for the resolution of 1,1′-bi-2-naphthol on the CSPs based on (S)-N-(3,5-dinitrobenzoyl)leucine N-propylamide and (S)-N-(3,5-dinitrobenzoyl)phenylglycine N-propylamide were opposite to those for the resolution of 3,3′-diaryl-1,1′-bi-2-naphthols. To rationalize the reversed elution orders, the authors proposed two different chiral recognition mechanisms based on the chromatog. resolution behaviors, with the aid of the CPK mol. model study. In the experiment, the researchers used many compounds, for example, (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6Application In Synthesis of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol).

(S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6) 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 (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A Poly(cobaloxime)/Carbon Nanotube Electrode: Freestanding Buckypaper with Polymer-Enhanced H₂-Evolution Performance was written by Reuillard, Bertrand;Warnan, Julien;Leung, Jane J.;Wakerley, David W.;Reisner, Erwin. And the article was included in Angewandte Chemie, International Edition in 2016.Safety of ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) This article mentions the following:

A freestanding H₂-evolution electrode consisting of a copolymer-embedded cobaloxime integrated into a multiwall C nanotube matrix by π-π interactions is reported. This electrode is straightforward to assemble and displays high activity towards H evolution in near-neutral pH solution under inert and aerobic conditions, with a Co-based turnover number (TON_Co) of up to 420. An analogous electrode with a monomeric cobaloxime showed less activity with a TON_Co of only 80. Probably in addition to the high surface area of the porous network of the buckypaper, the polymeric scaffold provides a stabilizing environment to the catalyst, leading to further enhancement in catalytic performance. The authors have therefore established that the use of a multifunctional copolymeric architecture is a viable strategy to enhance the performance of mol. electrocatalysts. 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: 109-17-1Safety of ((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.Safety of ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate)

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Palladium-Catalyzed Oxidative Nonclassical Heck Reaction of Arylhydrazines with Allylic Alcohols via C-N Bond Cleavage: Access to β-Arylated Carbonyl Compounds was written by Wang, Xiaoshuo;Wang, Xiaojing;Pan, Hongwu;Ming, Xiayi;Zhang, Zhenming;Wang, Tao. And the article was included in Journal of Organic Chemistry in 2022.Computed Properties of C8H16O This article mentions the following:

An efficient palladium-catalyzed oxidative nonclassical Heck reaction of arylhydrazines with allylic alcs. via C-N bond cleavage to form β-arylated carbonyl compounds I [R = Me, Et, Cy, etc.; R¹ = Ph, pentyl] was successfully developed. This method provided a series of β-arylated carbonyl compounds I with broad functional group tolerance under base-free, simple, and mild open air reaction conditions. In the reaction, arylhydrazines with the smaller mol. weight of the leaving group were employed as the “green”; arylation reagent, which released N₂ and water as the byproducts under air. Mechanistic studies suggested that an aryl radical process and Pd-H complex migration reinsertion were involved. Moreover, the synthesis of the antiarrhythmic drug propafenone was completed with this transformation as the key step. 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. Similar to water, an alcohol can be pictured as having an sp3 hybridized tetrahedral oxygen atom with nonbonding pairs of electrons occupying two of the four sp3 hybrid orbitals. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Computed Properties of C8H16O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kinetic analysis of the conversion of aqueous erythritol solution on Ir/ReO_x/TiO₂ in a batch slurry reactor was written by Virgilio, Emanuel M.;Sad, Maria E.;Padro, Cristina L.. And the article was included in Applied Catalysis, A: General in 2022.Application In Synthesis of (2R,3S)-rel-Butane-1,2,3,4-tetraol This article mentions the following:

The influence of temperature, H₂ pressure and erythritol concentration on the hydrogenolysis of erythritol was studied using Ir/ReO_x/TiO₂. Under the conditions used here, four reaction routes coexist: isomerization, dehydration, C-O and C-C hydrogenolysis. The initial rates as well as reaction orders and activation energy were estimated for each pathway. The variation of the hydrogen pressure produced slight changes in the isomerization, dehydration, and C-C hydrogenolysis routes, whereas C-O hydrogenolysis showed order 1 with respect to this reagent. The change in erythritol concentration affected more the dehydration, resulting in a reaction order for this reactant close to 1, while for the other routes the order was close to 0.5. Regarding the influence of the temperature, dehydration of erythritol showed the highest activation energy (212.1 kJ mol^-1) and the isomerization the lowest (20.0 kJ mol^-1). Furthermore, it was found that the ruptures of C-C bonds require higher energy than C-O bonds break. 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. 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 (2R,3S)-rel-Butane-1,2,3,4-tetraol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts