Tag: 100-200

Interplay Between Steric and Electronic Effects: A Joint Spectroscopy and Computational Study of Nonheme Iron(IV)-Oxo Complexes was written by Mukherjee, Gourab;Alili, Aligulu;Barman, Prasenjit;Kumar, Devesh;Sastri, Chivukula V.;de Visser, Sam P.. And the article was included in Chemistry – A European Journal in 2019.Application of 1122-71-0 This article mentions the following:

Iron is an essential element in nonheme enzymes that plays a crucial role in many vital oxidative transformations and metabolic reactions in the human body. Many of those reactions are regio- and stereospecific and it is believed that the selectivity is guided by second-coordination sphere effects in the protein. Here, results are shown of a few engineered biomimetic ligand frameworks based on the N4Py (N,N-bis(2-pyridylmethyl)-N-bis(2-pyridyl)methylamine) scaffold and the second-coordination sphere effects are studied. For the first time, selective substitutions in the ligand framework have been shown to tune the catalytic properties of the iron(IV)-oxo complexes by regulating the steric and electronic factors. In particular, a better positioning of the oxidant and substrate in the rate-determining transition state lowers the reaction barriers. Therefore, an optimum balance between steric and electronic factors mediates the ideal positioning of oxidant and substrate in the rate-determining transition state that affects the reactivity of high-valent reaction intermediates. 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. 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Application of 1122-71-0

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Novel substrates for efficient enzymatic transglycosylation by Bacillus circulans was written by Komba, Shiro;Ito, Yukishige. And the article was included in Canadian Journal of Chemistry in 2002.SDS of cas: 60463-12-9 This article mentions the following:

To develop transglycosylation for efficient preparation of N-acetyllactosamine (Galβ(1→4)GlcNAc, LacNAc), β-galactosidase mediated transglycosylation using novel substrates Bacillus Circulans was explored. To make transglycosylation entropically favorable over hydrolysis, donor (lactose or galactose) and acceptor (N-acetylglucosamine, GlcNAc) components were connected to a single mol. For that purpose, 1,2- and 1,3-benzenedimethanol and 2-hydroxy-5-nitro- and 5-hydroxy-2-nitro-benzyl alc. were screened as linkers and enzymic transglycosylation was examined under several conditions. In the case of 2-hydroxy-5-nitro-benzyl connected substrate 40, an indication of the occurrence of intramol. transglycosylation was observed, and the desired product (58) was obtained in 26% isolated yield. The same reaction in the presence of CMP sialic acid and α-(2→6)-sialyltransferase gave sialyl LacNAc 87 in one pot in 39% isolated yield. Addnl., the effect of the C-2 substituent of the acceptor component was briefly examined using substrates containing NHAlloc (72), NHTroc (73), and N₃ (74) groups. Although the occurrence of intramol. transglycosylation was not clear in these cases, disaccharides 81-83 were obtained in reasonable yields. In the experiment, the researchers used many compounds, for example, 3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9SDS of cas: 60463-12-9).

3-(Hydroxymethyl)-4-nitrophenol (cas: 60463-12-9) 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: 60463-12-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Catalytic β C-H amination via an imidate radical relay was written by Stateman, Leah M.;Wappes, Ethan A.;Nakafuku, Kohki M.;Edwards, Kara M.;Nagib, David A.. And the article was included in Chemical Science in 2019.COA of Formula: C9H9F3O This article mentions the following:

The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables β C-H amination of alcs. e.g., 4-trichloroacetamidyl cholesterol by an imidate-mediated radical relay. In contrast to the first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes (6-methyl-5-hepten-2-one, 3,7-dimethyl-2,6-octadienol), alkynes (isonicotinonitrile), alcs.(1-octanol), carbonyls (Me 2-(([(4-nitrobenzene)sulfonyl]oxy)amino)-3-phenylpropanoate) and heteroarenes (quinoline, benzofuran, benzo[b]thiophene, etc.). Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity. In the experiment, the researchers used many compounds, for example, 2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6COA of Formula: C9H9F3O).

2-(4-(Trifluoromethyl)phenyl)ethanol (cas: 2968-93-6) 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. 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.COA of Formula: C9H9F3O

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

A modular design of ruthenium catalysts with diamine and BINOL-derived phosphinite ligands that are enantiomerically-matched for the effective asymmetric transfer hydrogenation of simple ketones was written by Guo, Rongwei;Elpelt, Christian;Chen, Xuanhua;Song, Datong;Morris, Robert H.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2005.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol This article mentions the following:

A method is reported for making a potentially very wide series of ruthenium hydrido chloro complexes with diamine and readily-prepared diphosphinite ligand modules as precatalysts for the asym. transfer hydrogenation of simple ketones to give chiral alcs. in good yield and enantioselectivity. In the experiment, the researchers used many compounds, for example, (R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol).

(R)-1-(3-Chlorophenyl)ethanol (cas: 120121-01-9) 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. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Recommanded Product: (R)-1-(3-Chlorophenyl)ethanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Studies on agents with vasodilator and β-blocking activities. II was written by Seki, Toshimi;Takezaki, Takayuki;Ohuchi, Rikio;Ohuyabu, Hiroshi;Tanimoto, Yoshitaka;Yamaguchi, Takashi;Saitoh, Morinobu;Ishimori, Tsutomu;Yasuda, Kikuo. And the article was included in Chemical & Pharmaceutical Bulletin in 1995.COA of Formula: C5H13NO This article mentions the following:

Phenoxypropanolamines having a hydrazinopyridazinyl moiety I (n = integer; X = O, S; R = H, alkyl, etc.) were synthesized. Their hypotensive and β-blocking activities were evaluated after i.v. administration of the compounds to anesthetized rats. Some of them exhibited both activities. In particular, I (R = 2-chloro; n = 1; X = O) is a candidate for clin. use due to its hypotensive activity, equal to that of hydralazine, and its β-blocking activity, 2.4-fold more potent than that of propranolol. In the experiment, the researchers used many compounds, for example, 3-Amino-3-methylbutan-1-ol (cas: 42514-50-1COA of Formula: C5H13NO).

3-Amino-3-methylbutan-1-ol (cas: 42514-50-1) 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.COA of Formula: C5H13NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Stereoselective biocatalytic hydride transfer to substituted acetophenones by the yeast Metschnikowia koreensis was written by Singh, Amit;Chisti, Yusuf;Banerjee, U. C.. And the article was included in Process Biochemistry (Oxford, United Kingdom) in 2012.Product Details of 171032-87-4 This article mentions the following:

Freely suspended and variously entrapped viable cells of the yeast Metschnikowia koreensis were examined for the asym. reduction of prochiral acetophenone. A ketone substrate at 25 mM can be converted (92%) to the corresponding alc. within 3 h using freely suspended cells [46 mg/mL dry cell weight (DCW)] at pH 9 (Tris buffer, 50 mM), 25 °C, in an agitated reactor (200 rpm). The reaction displayed an excellent stereoselectivity of >99%. Supplementation of the reaction mixture with glucose (20 g/L) greatly enhanced the rate of the bioreduction reaction likely because of improved cofactor recycling in the cells. The cells could successfully reduce various acetophenones substituted with electron withdrawing groups on the Ph ring, particularly at the para-position compared to ortho- or meta-substituted acetophenones. The ketone reductase of M. koreensis showed Prelog-selectivity as the reaction exclusively yielded (S)-alcs. The thermostability and the substrate tolerance of the yeast were improved by immobilization in calcium alginate beads. Immobilization reduced the effectiveness factor only slightly. In the experiment, the researchers used many compounds, for example, (S)-1-(2-Fluorophenyl)ethanol (cas: 171032-87-4Product Details of 171032-87-4).

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Effect of polar molecular organic solvents on non-aqueous solvent extraction of rare-earth elements was written by Dewulf, Brecht;Cool, Vincent;Li, Zheng;Binnemans, Koen. And the article was included in Separation and Purification Technology in 2022.Application In Synthesis of 2,2′-Oxybis(ethan-1-ol) This article mentions the following:

The extraction and separation of five different rare-earth elements, La, Nd, Eu, Dy and Yb, from an aqueous chloride solution and from different chloride non-aqueous solutions using the solvating extractant Cyanex 923 was investigated. As previous studies had demonstrated the potential of non-aqueous solvent extraction (NASX) to refine rare earths from ethylene glycol, structural analogs of ethylene glycol (1,2-propanediol and 1,3-propanediol) and to other polar organic solvents (triethylene glycol, dimethylsulfoxide, methanol, N,N-dimethylformamide and N,N-dimethylacetamide) were studied. The extraction data were interpreted in terms of different solvent properties: dielec. constant, Gutmann donor number, mol. structure and hydrogen-bonding capabilities. Remarkable differences were observed between the extraction behavior from ethylene glycol, 1,2-propanediol and 1,3-propanediol. Therefore, these solvent systems were further studied to elucidate the speciation of the rare-earth elements by optical absorption and luminescence spectroscopy. Based on these studies, both contact-ion-pair formation and solvation strength are assumed to play an important role in the extraction of rare earths by Cyanex 923 from different polar organic solvents. The differences in extraction behavior can be exploited to fine-tune the separation of rare earths. In the experiment, the researchers used many compounds, for example, 2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6Application In Synthesis of 2,2′-Oxybis(ethan-1-ol)).

2,2′-Oxybis(ethan-1-ol) (cas: 111-46-6) 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Application In Synthesis of 2,2′-Oxybis(ethan-1-ol)

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

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

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