Month: January 2023

A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions was written by Ota, Eisuke;Wang, Huaiju;Frye, Nils Lennart;Knowles, Robert R.. And the article was included in Journal of the American Chemical Society in 2019.Safety of tert-Butyl (trans-2-hydroxycyclohexyl)carbamate This article mentions the following:

We report a general protocol for the light-driven isomerization of cyclic aliphatic alcs. to linear carbonyl compounds These reactions proceed via proton-coupled electron-transfer activation of alc. O-H bonds followed by subsequent C-C β-scission of the resulting alkoxy radical intermediates. In many cases, these redox-neutral isomerizations proceed in opposition to a significant energetic gradient, yielding products that are less thermodynamically stable than the starting materials. A mechanism is presented to rationalize this out-of-equilibrium behavior that may serve as a model for the design of other contrathermodynamic transformations driven by excited-state redox events. In the experiment, the researchers used many compounds, for example, tert-Butyl (trans-2-hydroxycyclohexyl)carbamate (cas: 121282-70-0Safety of tert-Butyl (trans-2-hydroxycyclohexyl)carbamate).

tert-Butyl (trans-2-hydroxycyclohexyl)carbamate (cas: 121282-70-0) belongs to alcohols. Alkyl halides are often synthesized from alcohols, in effect substituting a halogen atom for the hydroxyl group. 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 tert-Butyl (trans-2-hydroxycyclohexyl)carbamate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cu(II) Schiff base complex supported on Fe₃O₄ nanoparticles as an efficient nanocatalyst for the selective aerobic oxidation of alcohols was written by Aghajani, Milad;Monadi, Niaz. And the article was included in Applied Organometallic Chemistry in 2018.Category: alcohols-buliding-blocks This article mentions the following:

A new Cu(II) Schiff base complex supported onto the surface of modified Fe₃O₄ nanoparticles was prepared and used as highly stable, heterogeneous and magnetically recyclable nanocatalyst for the selective aerobic oxidation of various primary and secondary alcs. to the corresponding aldehydes or ketones. The structure, morphol., chem. composition and magnetic property of the nanocatalyst and its precursors were characterized using FT-IR, TGA, AAS, ICP-AES, XRD, SEM, EDS, VSM and N₂ adsorption-desorption anal. Characterization results exhibited the uniform spherical morphol. for nanocatalyst and its precursors. A promising eco-friendly method with short reaction time and high conversion and selectivity for oxidation of various primary and secondary alcs. under O₂ atmosphere condition was achieved. The synthesized nanocatalyst could be recovered easily by applying an external magnetic field and reused for least eight subsequent reaction cycles with only negligible deterioration in catalytic performance. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Category: alcohols-buliding-blocks).

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

Zwitterionic hydrogels implanted in mice resist the foreign-body reaction was written by Zhang, Lei;Cao, Zhiqiang;Bai, Tao;Carr, Louisa;Ella-Menye, Jean-Rene;Irvin, Colleen;Ratner, Buddy D.;Jiang, Shaoyi. And the article was included in Nature Biotechnology in 2013.HPLC of Formula: 109-17-1 This article mentions the following:

The performance of implantable biomedical devices is impeded by the foreign-body reaction, which results in formation of a dense collagenous capsule that blocks mass transport and/or elec. communication between the implant and the body. No known materials or coatings can completely prevent capsule formation. Here we demonstrate that ultra-low-fouling zwitterionic hydrogels can resist the formation of a capsule for at least 3 mo after s.c. implantation in mice. Zwitterionic hydrogels also promote angiogenesis in surrounding tissue, perhaps owing to the presence of macrophages exhibiting phenotypes associated with anti-inflammatory, pro-healing functions. Thus, zwitterionic hydrogels may be useful in a broad range of applications, including generation of biocompatible implantable medical devices and tissue scaffolds. 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: 109-17-1HPLC of Formula: 109-17-1).

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Migration of acyl groups in the orcinol series was written by Mauthner, Nandor. And the article was included in Journal fuer Praktische Chemie (Leipzig) in 1942.COA of Formula: C9H10O3 This article mentions the following:

1,3,5-C₆H₃Me(OAc)₂ and AlCl₃PhNO₂ at room temperature yield (mainly) 1,3-diketo-2,4-diacetyl-5-methyl-1,2,3,4-tetrahydrobenzene, m. 93-4° (mono-p-nitrophenylhydrazone, m. 225-6°), a little 3,5,1,4-(HO)₂C₆H₂MeCOMe (p-nitrophenylhydrazone, m. 257-8°), and a substance, m. 55-6°, b₁₂ 163-4° (no reaction with p-NO₂C₆H₄NHNH₂). In the experiment, the researchers used many compounds, for example, 2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0COA of Formula: C9H10O3).

2′,6′-Dihydroxy-4′-methylacetophenone (cas: 1634-34-0) 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.COA of Formula: C9H10O3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Exploitation of Amine Groups Cooped up in Polyamide Nanofiltration Membranes to Achieve High Rejection of Micropollutants and High Permeance of Divalent Cations was written by Gao, Yawei;Wang, Kunpeng;Wang, Xiao-mao;Huang, Xia. And the article was included in Environmental Science & Technology in 2022.Name: (2R,3S)-rel-Butane-1,2,3,4-tetraol This article mentions the following:

To enhance the use of nanofiltration in the production of quality drinking water, particularly through the efficient removal of micropollutants yet still preserving essential minerals, the targeted nanofiltration membranes (NFMs) are required to have small pore dimensions coupled with a high, net-neg. charge d. Herein, after the formation of a separation layer using piperazine interfacially polymerized with trimesoyl chloride, the exploitation of residual amine groups was systematically investigated by different diacyl chlorides in an organic milieu, which caused the upper part of the final separation layer to be denser and highly neg. charged. Hence, this protocol offers a novel means to fabricate NFMs simultaneously endowed with a low mol. cutoff (MWCO) of 145-238 Da and a reduced rejection of MgCl₂ (48%-80%) as well as a competitive water permeance. Those features are ideally applicable to the goal of removing small micropollutants while preserving mineral ions, as needed for the energy-efficient production of safe, quality drinking water. Furthermore, an attempt was made to correlate MWCO with MgCl₂ rejection, which provides some insights on the nexus of the electrostatic effects constrained by size exclusion. The significance of residual amine groups and the modification environment was unveiled, and this method paves a new avenue for designing functional NFMs. In the experiment, the researchers used many compounds, for example, (2R,3S)-rel-Butane-1,2,3,4-tetraol (cas: 149-32-6Name: (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 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. 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: (2R,3S)-rel-Butane-1,2,3,4-tetraol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Effect of a Calcium Prerinse on Salivary Fluoride after a 228-ppm Fluoride Rinse was written by Vogel, G. L.;Chow, L. C.;Carey, C. M.;Schumacher, G. E.;Takagi, S.. And the article was included in Caries Research in 2006.Safety of Calcium 2-hydroxypropanoate pentahydrate This article mentions the following:

The objective of this study was to determine if a concentrated calcium prerinse given before a fluoride rinse would cause an increase in the post rinse salivary fluoride (F). A panel of 5 subjects used a 30, 150 or 300 mmol/l calcium lactate prerinse followed by a 1-min NaF rinse. All calcium prerinses significantly increased the 1-h saliva F relative to the NaF control without a prerinse. The maximum increase was produced by the 150 mmol/l calcium lactate prerinse and was about ninefold higher than the NaF control. In the experiment, the researchers used many compounds, for example, Calcium 2-hydroxypropanoate pentahydrate (cas: 5743-47-5Safety of Calcium 2-hydroxypropanoate pentahydrate).

Calcium 2-hydroxypropanoate pentahydrate (cas: 5743-47-5) 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. 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.Safety of Calcium 2-hydroxypropanoate pentahydrate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Novel anti-Prelog stereospecific carbonyl reductases from Candida parapsilosis for asymmetric reduction of prochiral ketones was written by Nie, Yao;Xiao, Rong;Xu, Yan;Montelione, Gaetano T.. And the article was included in Organic & Biomolecular Chemistry in 2011.Formula: C8H9ClO This article mentions the following:

The application of biocatalysis to the synthesis of chiral mols. is one of the greenest technologies for the replacement of chem. routes due to its environmentally benign reaction conditions and unparalleled chemo-, regio- and stereoselectivities. We have been interested in searching for carbonyl reductase enzymes and assessing their substrate specificity and stereoselectivity. We now report a gene cluster identified in Candida parapsilosis that consists of four open reading frames including three putative stereospecific carbonyl reductases (scr1, scr2, and scr3) and an alc. dehydrogenase (cpadh). These newly identified three stereospecific carbonyl reductases (SCRs) showed high catalytic activities for producing (S)-1-phenyl-1,2-ethanediol from 2-hydroxyacetophenone with NADPH as the coenzyme. Together with CPADH, all four enzymes from this cluster are carbonyl reductases with novel anti-Prelog stereoselectivity. SCR1 and SCR3 exhibited distinct specificities to acetophenone derivatives and chloro-substituted 2-hydroxyacetophenones, and especially very high activities towards Et 4-chloro-3-oxobutyrate, a β-ketoester with important pharmaceutical potential. Our study also showed that genomic mining is a powerful tool for the discovery of new enzymes. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Formula: C8H9ClO).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. 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: C8H9ClO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Fine-tuning of the substrate binding mode to enhance the catalytic efficiency of an ortho-haloacetophenone-specific carbonyl reductase was written by Li, Aipeng;Li, Xue;Pang, Wei;Tian, Qing;Wang, Ting;Zhang, Lianbing. And the article was included in Catalysis Science & Technology in 2020.Application of 171032-87-4 This article mentions the following:

Carbonyl reductase BaSDR1 has been identified as a potential ortho-haloacetophenone-specific biocatalyst for the synthesis of chiral 1-(2-halophenyl)ethanols due to its excellent stereoselectivity. However, the catalytic efficiency of BaSDR1 is far below the required level for practical applications. Thus, fine-tuning of the substrate binding mode, which aimed at maximum preservation of the pos. factors for substrate specificity and stereoselectivity, was proposed as a tentative strategy for enhancing its catalytic efficiency. The designed mutants Q139S, D253Y and Q139S/D253Y showed significantly enhanced catalytic efficiency. Remarkably, the variants Q139S and Q139S/D253Y exhibited a more than 9-fold improvement in catalytic efficiency (k_cat/K_m) toward substrates 6a and 11a, resp. More importantly, none of the variants caused activity-stereoselectivity trade-off and all variants exhibited excellent stereoselectivity (99% ee). Anal. of variant-substrate complexes showed that the mutations indeed enable the fine-tuning of the substrate binding mode. New strengthening factors for consolidating the productive conformation were introduced while the original pos. factors were preserved. Furthermore, at a substrate concentration of 100 mM, recombinant E. coli whole cells expressing the BaSDR1 mutants were successfully applied to the synthesis of several key intermediates of chiral pharmaceuticals, including (S)-1-(2-chlorophenyl)ethanol, (S)-1-(2,4-difluorophenyl)ethanol and (S)-1-(2,6-difluorophenyl)ethanol, with 99% enantiomeric excess, and the conversion reached over 95% in a certain period of time. These results demonstrated the effectiveness of the strategy involving the fine-tuning of the substrate binding mode and the applicability of the designed mutants in efficient reduction of ortho-haloacetophenones. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Application of 171032-87-4).

(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. 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.Application of 171032-87-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Flat corannulene: when a transition state becomes a stable molecule was written by Solel, Ephrath;Pappo, Doron;Reany, Ofer;Mejuch, Tom;Gershoni-Poranne, Renana;Botoshansky, Mark;Stanger, Amnon;Keinan, Ehud. And the article was included in Chemical Science in 2020.Quality Control of Sodium 2-methyl-2-propanethiolate This article mentions the following:

Flat corannulene has been considered so far only as a transition state of the bowl-to-bowl inversion process. This study was driven by the prediction that substituents with strong steric repulsion could destabilize the bowl-shaped conformation of this mol. to such an extent that the highly unstable planar geometry would become an isolable mol. To examine the substituents’ effect on the corannulene bowl depth, optimized structures for the highly-congested decakis(t-butylsulfido)corannulene were calculated The computations, performed with both the M06-2X/def2-TZVP and the B3LYP/def2-TZVP methods (the latter with and without Grimme’s D3 dispersion correction), predict that this mol. can achieve two min. structures: a flat carbon framework and a bowl-shaped structure, which are very close in energy. This rather unusual compound was easily synthesized from decachlorocorannulene under mild reaction conditions, and X-ray crystallog. studies gave similar results to the theor. predictions. This compound crystallized in two different polymorphs, one exhibiting a completely flat corannulene core and the other having a bowl-shaped conformation. In the experiment, the researchers used many compounds, for example, Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2Quality Control of Sodium 2-methyl-2-propanethiolate).

Sodium 2-methyl-2-propanethiolate (cas: 29364-29-2) 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of Sodium 2-methyl-2-propanethiolate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reduction of aliphatic, aromatic and heteroaromatic carboxylic acid derivatives to alcohol promoted by trityl resin under presence of copper sulphate and sodium borohydride catalytic system was written by Kalola, Anirudhdha G.;Prasad, Pratibha;Patel, Manish P.. And the article was included in Heterocyclic Letters in 2022.Computed Properties of C7H6Cl2O This article mentions the following:

An efficient, eco-friendly, mild protocol for the acid-alc. transformation is developed. Varied aliphatic, aromatic and heteroaromatic carboxylic acid derivatives RC(O)OH [R = n-heptadecan-1-yl, 1-naphthyl, furan-2-yl, etc.] loaded on to the 2-chloro trityl chloride resin under perseverance of DIPEA base followed by subsequent reduction into corresponding alcs. ROH using CuSO₄-NaBH₄ catalytic system have been achieved in excellent yield with easy product isolation technique. Facile recycling of the recovered resin is also associated to this methodol. In the experiment, the researchers used many compounds, for example, (2,4-Dichlorophenyl)methanol (cas: 1777-82-8Computed Properties of C7H6Cl2O).

(2,4-Dichlorophenyl)methanol (cas: 1777-82-8) 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. 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.Computed Properties of C7H6Cl2O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts