Month: February 2023

Indium(III)-Catalyzed Synthesis of Primary Carbamates and N-Substituted Ureas was written by Jain, Isha;Malik, Payal. And the article was included in Synlett in 2022.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol This article mentions the following:

An indium triflate-catalyzed synthesis of primary carbamates RXC(O)NH₂ [R = i-Bu, Bn, Ph, etc.; X= O, N] from alcs. and urea as an ecofriendly carbonyl source was developed. Various linear, branched, and cyclic alcs. were converted into the corresponding carbamates in good to excellent yields. This method also provided access to N-substituted ureas by carbamoylation of amines. All the products were obtained by simple filtration or crystallization, without the need for chromatog. purification Mechanistic investigations suggested that the carbamoylation reaction proceeded through activation of urea by O-coordination with indium, followed by nucleophilic attack by the alc. or amine on the carbonyl center of urea. The inexpensive and easily available starting materials and catalyst, the short reaction times, and the ease of product isolation highlighted the inherent practicality of the developed method. 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. 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.Application In Synthesis of (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Structure-Activity Relationship Explorations and Discovery of a Potent Antagonist for the Free Fatty Acid Receptor 2 was written by Hoejgaard Hansen, Anders;Christensen, Henriette B.;Pandey, Sunil K.;Sergeev, Eugenia;Valentini, Alice;Dunlop, Julia;Dedeo, Domonkos;Fratta, Simone;Hudson, Brian D.;Milligan, Graeme;Ulven, Trond;Rexen Ulven, Elisabeth. And the article was included in ChemMedChem in 2021.Recommanded Product: 2968-93-6 This article mentions the following:

Free fatty acid receptor 2 (FFA2) is a sensor for short-chain fatty acids that has been identified as an interesting potential drug target for treatment of metabolic and inflammatory diseases. Although several ligand series are known for the receptor, there is still a need for improved compounds One of the most potent and frequently used antagonists is the amide-substituted phenylbutanoic acid known as CATPB (1). We here report the structure-activity relationship exploration of this compound, leading to the identification of homologues with increased potency. The preferred compound 37 (TUG-1958) was found, besides improved potency, to have high solubility and favorable pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6Recommanded Product: 2968-93-6).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) belongs to alcohols. The oxygen atom of the strongly polarized O鈥旽 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. 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.Recommanded Product: 2968-93-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

[Lewis acid]⁺[Co(CO)₄]^– complexes: A versatile class of catalysts for carbonylative ring expansion of epoxides and aziridines was written by Mahadevan, Viswanath;Getzler, Yutan D. Y. L.;Coates, Geoffrey W.. And the article was included in Angewandte Chemie, International Edition in 2002.Quality Control of Trans-2-(benzylamino)cyclohexanol This article mentions the following:

Efficient carbonyl insertion into C-O and C-N bonds using [Lewis acid]-⁺[Co(CO)₄]^– complexes [Cp₂Ti(thf)₂][Co(CO)₄] 1 and [(salph)Al(thf)₂][Co(CO)₄] 2 [salph = N,N’-bis(3,5-di-tert-butylsalicylidene)phenylenediamine] gives regio- and stereoselective carbonylation of a variety of epoxides and aziridines to yield 尾-lactones and 尾-lactams, resp. Both transformations are proposed to occur by the same mechanism, yielding products with inversion of configuration at the site of CO insertion. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Quality Control of Trans-2-(benzylamino)cyclohexanol).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Quality Control of Trans-2-(benzylamino)cyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase SmADH2 via an environmentally friendly TBCR system was written by Yang, Zeyu;Fu, Hengwei;Ye, Wenjie;Xie, Youyu;Liu, Qinghai;Wang, Hualei;Wei, Dongzhi. And the article was included in Catalysis Science & Technology in 2020.Quality Control of (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

Alc. dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asym. synthesis of chiral alcs.; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the byproduct, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technol. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, volume/volume) concentration Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the byproduct acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcs. are synthesized at a high substrate loading (>150 g L^-1) without adding external coenzymes. Among these, about 780 g L^-1 (6 M) Et acetoacetate is completely converted into Et (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L^-1 d^-1 space-time yield. Mol. dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcs. on an industrial scale. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Quality Control of (R)-1-(3-Chlorophenyl)ethanol).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Quality Control of (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

High toughness of blood compatible polymer and 3D printing was written by Asai, Fumio;Nagoya, Chembio. And the article was included in Kobunshi in 2022.Quality Control of Diethyleneglycoldiacrylate This article mentions the following:

In Japan today, the era of 100-yr life expectancy is fast approaching as the average life expectancy of the Japanese people increases year by year. Realization of new therapeutic techniques in the medical field is indispensable for the formation of a healthy and long-lived society, and research and development of medical polymer materials that can meet unmet medical needs is important. Against this background, in this study, we combined different materials, i.e., polymers and Japanese inorganic particles, to create medical polymer with self-adhesive properties for the realization of small-diameter artificial blood vessels. In the experiment, the researchers used many compounds, for example, Diethyleneglycoldiacrylate (cas: 4074-88-8Quality Control of Diethyleneglycoldiacrylate).

Diethyleneglycoldiacrylate (cas: 4074-88-8) 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.Quality Control of Diethyleneglycoldiacrylate

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A base promoted multigram synthesis of aminoisoxazoles: valuable building blocks for drug discovery and peptidomimetics was written by Chalyk, Bohdan A.;Kandaurova, Inna Y.;Hrebeniuk, Kateryna V.;Manoilenko, Olga V.;Kulik, Irene B.;Iminov, Rustam T.;Kubyshkin, Vladimir;Tverdokhlebov, Anton V.;Ablialimov, Osman K.;Mykhailiuk, Pavel K.. And the article was included in RSC Advances in 2016.Name: 1-Boc-Azetidine-3-yl-methanol This article mentions the following:

A practical multigram metal free synthesis of isoxazole-containing building blocks from com. available amino acids was elaborated. The key reaction was a regioselective [3+2]-cycloaddition of in-situ generated nitrile oxides with alkynes/enamines. The obtained building blocks were used in the preparation of bioactive compounds and peptidomimetics. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Name: 1-Boc-Azetidine-3-yl-methanol).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Name: 1-Boc-Azetidine-3-yl-methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Design and synthesis of cyanamides as potent and selective N-acylethanolamine acid amidase inhibitors was written by Malamas, Michael S.;Farah, Shrouq I.;Lamani, Manjunath;Pelekoudas, Dimitrios N.;Perry, Nicholas Thomas;Rajarshi, Girija;Miyabe, Christina Yume;Chandrashekhar, Honrao;West, Jay;Pavlopoulos, Spiro;Makriyannis, Alexandros. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Synthetic Route of C9H17NO3 This article mentions the following:

N-acylethanolamine acid amidase (NAAA) inhibition represents an exciting novel approach to treat inflammation and pain. NAAA is a cysteine amidase which preferentially hydrolyzes the endogenous biolipids palmitoylethanolamide (PEA) and oleoylethanolamide (OEA). PEA is an endogenous agonist of the nuclear peroxisome proliferator-activated receptor-伪 (PPAR-伪), which is a key regulator of inflammation and pain. Thus, blocking the degradation of PEA with NAAA inhibitors results in augmentation of the PEA/PPAR-伪 signaling pathway and regulation of inflammatory and pain processes. We have prepared a new series of NAAA inhibitors exploring the azetidine-nitrile (cyanamide) pharmacophore that led to the discovery of highly potent and selective compounds Key analogs demonstrated single-digit nanomolar potency for hNAAA and showed >100-fold selectivity against serine hydrolases FAAH, MGL and ABHD6, and cysteine protease cathepsin K. Addnl., we have identified potent and selective dual NAAA-FAAH inhibitors to investigate a potential synergism between two distinct anti-inflammatory mol. pathways, the PEA/PPAR-伪 anti-inflammatory signaling pathway,^1-4 and the cannabinoid receptors CB1 and CB2 pathways which are known for their antiinflammatory and antinociceptive properties.^5-8 Our ligand design strategy followed a traditional structure-activity relationship (SAR) approach and was supported by mol. modeling studies of reported X-ray structures of hNAAA. Several inhibitors were evaluated in stability assays and demonstrated very good plasma stability (t_1/2 > 2 h; human and rodents). The disclosed cyanamides represent promising new pharmacol. tools to investigate the potential role of NAAA inhibitors and dual NAAA-FAAH inhibitors as therapeutic agents for the treatment of inflammation and pain. In the experiment, the researchers used many compounds, for example, 1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3Synthetic Route of C9H17NO3).

1-Boc-Azetidine-3-yl-methanol (cas: 142253-56-3) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. 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.Synthetic Route of C9H17NO3

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Polymer-Network Toughening and Highly Sensitive Mechanochromism via a Dynamic Covalent Mechanophore and a Multinetwork Strategy was written by Watabe, Takuma;Aoki, Daisuke;Otsuka, Hideyuki. And the article was included in Macromolecules (Washington, DC, United States) in 2022.Application In Synthesis of ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate) This article mentions the following:

Multinetwork (MN) elastomers exhibit outstanding mech. properties that arise from the sacrificial first network (FN). Here, we report the mech. and mechanochromic properties of an MN elastomer with a difluorenylsuccinonitrile (DFSN) moiety incorporated into the crosslinking points of its FN. DFSN is a mechanochromophore that affords stable, pink radical intermediates upon exposure to mech. stimuli. We distinctly demonstrated that the replacement of a conventional cross-linker by a weaker cross-linker does have a direct effect on the stress-strain behavior of elastomers to improve fracture toughness. The toughening mechanism of the DFSN-containing MN elastomers was revealed through a highly sensitive and quant. anal. of the mech. activated stable radicals by ESR spectroscopy. We also clarified that the MN strategy is an effective technique to achieve high activation of the mechanophores at a lower threshold strain. 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: 109-17-1Application In Synthesis 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. A strong base can deprotonate an alcohol to yield an alkoxide ion (R鈥昈鈭?. 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.Application In Synthesis of ((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethane-2,1-diyl) bis(2-methylacrylate)

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Preparation of a new chiral stationary phase based on (2S,3S)-O,O’-bis-(10-undecenoyl)-N,N’-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butanediol and its application for the liquid chromatographic resolution of enantiomers was written by Hyun, Myung Ho;Boo, Chang Jin;Choi, Hee Jung;Kim, Yun Kyoung;Kang, Bu Sung;Ha, Hyun Ju;Choi, Min Ki;Tan, Guanghui. And the article was included in Bulletin of the Korean Chemical Society in 2006.Quality Control of (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol This article mentions the following:

A new liquid chromatog. chiral stationary phase based on (2S,3S)-O,O’-bis-(10-undecenoyl)-N,N’-bis-(3,5-dinitrobenzoyl)-2,3-diamino-1,4-butanediol was prepared starting from (2R,3R)-1,4-bis(benzyloxy)-2,3-butanediol. The new chiral stationary phase was applied to the resolution of racemic anilide derivatives of N-acetyl-伪-amino acids, 1,1′-bi-2-naphthol and 3,3′-diaryl-1,1′-bi-2-naphthols. It was also applied to the resolution of some chiral drugs including bendroflumethiazide, naproxen and alminoprofen. In every case, the chiral recognition efficiency of the new CSP was quite excellent. In the experiment, the researchers used many compounds, for example, (S)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol (cas: 863659-89-6Quality Control 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. 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)-[2,3′:1′,1”:3”,2”’-Quaternaphthalene]-2′,2”-diol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Industrially viable process for reduction of esters to alcohols with sodium borohydride under buffer and aqueous alcoholic conditions was written by Chavakula, Ramadas;Rao, M. Narayana;Babu, B. Gopi;Kumar, K. Praveen;Rao, Ch. Srinivasa. And the article was included in Journal of the Indian Chemical Society in 2014.Application In Synthesis of (5-Methylpyridin-3-yl)methanol This article mentions the following:

A simple and convenient procedure for the synthesis of alcs. from esters by reduction method using sodium borohydride in the presence of dipotassium hydrogen orthophosphate under aqueous alc. conditions is described. This method uses inexpensive, safe and environmentally friendly reducing agent. In the experiment, the researchers used many compounds, for example, (5-Methylpyridin-3-yl)methanol (cas: 102074-19-1Application In Synthesis of (5-Methylpyridin-3-yl)methanol).

(5-Methylpyridin-3-yl)methanol (cas: 102074-19-1) 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.Application In Synthesis of (5-Methylpyridin-3-yl)methanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts