Tag: 200-300

Highly regioselective ring-opening of epoxides with amines: a metal- and solvent-free protocol for the synthesis of β-amino alcohols was written by Li, Dong;Wang, Jing;Yu, Shibo;Ye, Silei;Zou, Wenjie;Zhang, Hongbin;Chen, Jingbo. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Application In Synthesis of Trans-2-(benzylamino)cyclohexanol This article mentions the following:

Herein, a metal- and solvent-free acetic acid-mediated ring-opening reaction of epoxides with amines was reported. This process provided β-amino alcs. R¹CH(OH)CH(R²)N(R³R⁴) [R¹ = H, CH₂OH, Ph; R² = H, Ph; R¹R² = (CH₂)₃, (CH₂)₄; R³ = H; R⁴ = Ph, Bn, 4-MeOC₆H₄, etc.; R³R⁴ = (CH₂)₄, (CH₂)₅, (CH₂)₂O(CH₂)₂] in high yields with excellent regioselectivity. Importantly, this epoxide ring-opening protocol was used for the introduction of amines in natural products during late-stage transformations. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Application In Synthesis of Trans-2-(benzylamino)cyclohexanol).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) 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. 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 Trans-2-(benzylamino)cyclohexanol

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Direct Synthesis of Boron-Protected Alkenyl- and Alkylborons via Copper-Catalyzed Formal Hydroboration of Alkynes and Alkenes was written by Yoshida, Hiroto;Takemoto, Yuki;Takaki, Ken. And the article was included in Asian Journal of Organic Chemistry in 2014.Application of 1214264-88-6 This article mentions the following:

Formal hydroboration of internal alkynes proceeds regio- and stereoselectively by the use of a diboron reagent masked with 1,8-diaminonaphthalene (dan) in the presence of readily available [(Ph₃P)₃CuCl], leading to direct formation of diverse B-protected alkenylborons in high yield. The B(dan) moiety can also be efficiently installed into the C-C double bond of alkenes to afford the resp. alkylborons. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Application of 1214264-88-6).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) 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.Application of 1214264-88-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Studies to further investigate the inhibition of human liver microsomal CYP2C8 by the acyl-β-glucuronide of gemfibrozil was written by Jenkins, S. M.;Zvyaga, T.;Johnson, S. R.;Hurley, J.;Wagner, A.;Burrell, R.;Turley, W.;Leet, J. E.;Philip, T.;Rodrigues, A. D.. And the article was included in Drug Metabolism and Disposition in 2011.Recommanded Product: 59960-32-6 This article mentions the following:

In previous studies, gemfibrozil acyl-β-glucuronide, but not gemfibrozil, was found to be a mechanism-based inhibitor of cytochrome P 450 2C8. To better understand whether this inhibition is specific for gemfibrozil acyl-β-glucuronide or whether other glucuronide conjugates are potential substrates for inhibition of this enzyme, we evaluated several pharmaceutical compounds (as their acyl glucuronides) as direct-acting and metabolism-dependent inhibitors of CYP2C8 in human liver microsomes. Of 11 compounds that were evaluated as their acyl glucuronide conjugates, only gemfibrozil acyl-β-glucuronide exhibited mechanism-based inhibition, indicating that CYP2C8 mechanism-based inhibition is very specific to certain glucuronide conjugates. Structural analogs of gemfibrozil were synthesized, and their glucuronide conjugates were prepared to further examine the mechanism of inhibition. When the aromatic Me groups on the gemfibrozil moiety were substituted with trifluoromethyls, the resulting glucuronide conjugate was a weaker inhibitor of CYP2C8 and mechanism-based inhibition was abolished. However, the glucuronide conjugates of monomethyl gemfibrozil analogs were mechanism-based inhibitors of CYP2C8, although not as potent as gemfibrozil acyl-β-glucuronide itself. The ortho-monomethyl analog was a more potent inhibitor than the meta-monomethyl analog, indicating that CYP2C8 favors the ortho position for oxidation and potential inhibition. Mol. modeling of gemfibrozil acyl-β-glucuronide in the CYP2C8 active site is consistent with the ortho-Me position being the favored site of covalent attachment to the heme. Moreover, hydrogen bonding to four residues (Ser100, Ser103, Gln214, and Asn217) is implicated. In the experiment, the researchers used many compounds, for example, 2-(3-(Hydroxy(phenyl)methyl)phenyl)propanoic acid (cas: 59960-32-6Recommanded Product: 59960-32-6).

2-(3-(Hydroxy(phenyl)methyl)phenyl)propanoic acid (cas: 59960-32-6) 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. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Recommanded Product: 59960-32-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electrochemically generated base synthesis of thiazolidine-2-thiones was written by Medini, Hayet;Mekni, Nejib Hussein;Boujlel, Khaled. And the article was included in Journal of Sulfur Chemistry in 2015.Formula: C13H19NO This article mentions the following:

The electrolysis of secondary β-amino alcs. in the presence of carbon disulfide using an electrogenerated base (EGB) to promote the reaction of the synthesis of thiazolidine-2-thione was reported. The EGB was prepared by probase-free electrolysis of acetonitrile under galvanostatic conditions using a sacrificial magnesium anode. The reaction produced the corresponding heterocyclic thiazolidine-2-thiones in satisfactory yields. The compounds thus obtained were fully characterized by IR, ¹H, ¹³C NMR spectroscopy, HRMS and elementary anal. In the experiment, the researchers used many compounds, for example, Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6Formula: C13H19NO).

Trans-2-(benzylamino)cyclohexanol (cas: 40571-86-6) 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.Formula: C13H19NO

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

High-Throughput Assessment and Modeling of a Polymer Library Regulating Human Dental Pulp-Derived Stem Cell Behavior was written by Rasi Ghaemi, Soraya;Delalat, Bahman;Gronthos, Stan;Alexander, Morgan R.;Winkler, David A.;Hook, Andrew L.;Voelcker, Nicolas H.. And the article was included in ACS Applied Materials & Interfaces in 2018.Name: Diethyleneglycoldiacrylate This article mentions the following:

The identification of biomaterials that modulate cell responses is a crucial task for tissue engineering and cell therapy. The identification of novel materials is complicated by the immense number of synthesizable polymers and the time required for testing each material exptl. In the current study, polymeric biomaterial-cell interactions were assessed rapidly using a microarray format. The attachment, proliferation, and differentiation of human dental pulp stem cells (hDPSCs) were investigated on 141 homopolymers and 400 diverse copolymers. The copolymer of isooctyl acrylate and 2-(methacryloyloxy)ethyl acetoacetate achieved the highest attachment and proliferation of hDPSC, whereas high cell attachment and differentiation of hDPSC were observed on the copolymer of isooctyl acrylate and trimethylolpropane ethoxylate triacrylate. Computational models were generated, relating polymer properties to cellular responses. These models could accurately predict cell behavior for up to 95% of materials within a test set. The models identified several functional groups as being important for supporting specific cell responses. In particular, oxygen-containing chem. moieties, including fragments from the acrylate/acrylamide backbone of the polymers, promoted cell attachment. Small hydrocarbon fragments originating from polymer pendant groups promoted cell proliferation and differentiation. These computational models constitute a key tool to direct the discovery of novel materials within the enormous chem. space available to researchers. In the experiment, the researchers used many compounds, for example, Diethyleneglycoldiacrylate (cas: 4074-88-8Name: Diethyleneglycoldiacrylate).

Diethyleneglycoldiacrylate (cas: 4074-88-8) 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.Name: Diethyleneglycoldiacrylate

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Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Plant cell cultures of Nordic berry species: Phenolic and carotenoid profiling and biological assessments was written by Rischer, Heiko;Nohynek, Liisa;Puupponen-Pimia, Riitta;Aguiar, Joselin;Rocchetti, Gabriele;Lucini, Luigi;Camara, Jose S.;Mendanha Cruz, Thiago;Boscacci Marques, Mariza;Granato, Daniel. And the article was included in Food Chemistry in 2022.SDS of cas: 10083-24-6 This article mentions the following:

Plant cell cultures from cloudberry (CL), lingonberry (LI), stone berry (ST), arctic bramble (AB), and strawberry (SB) were studied in terms of their polyphenol and carotenoid composition, antioxidant activity, antihemolytic activity and cytotoxicity effects on cancerous cells. High-resolution mass spectrometry data showed that LI, presented the highest antioxidant activity, contained the highest contents of flavones, phenolic acids, lignans, and total carotenoids, while CL, ST and SB presented the opposite behavior. AB and SB presented the lowest FRAP and CUPRAC values, while AB and CL presented the lowest reducing power. SB presented the lowest antioxidant activity measured by single electron transfer assays and the lowest content of lignans, phenolic acids, and flavones. CL and LI decreased the viability of in vitro mammary gland adenocarcinoma while only LI decreased the viability of in vitro lung carcinoma and showed protective effects of human erythrocytes against mech. hemolysis. In the experiment, the researchers used many compounds, for example, (E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6SDS of cas: 10083-24-6).

(E)-4-(3,5-Dihydroxystyryl)benzene-1,2-diol (cas: 10083-24-6) 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.SDS of cas: 10083-24-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Visible light-activated ruthenium-catalyzed direct arylation at ambient temperature was written by Li, Xuan;Chen, Mengnan;Xie, Chuan;Zhang, Jing. And the article was included in Tetrahedron Letters in 2022.Related Products of 68716-49-4 This article mentions the following:

A visible light-activated ruthenium-catalyzed direct arylation of aryl C-H bonds 1-R-2-R¹-3-R²-4-R³C₆H₂ (R = 5-methyl-1H-pyrazol-1-yl, isoquinolin-1-yl, 1H-indazol-1-yl, etc.; R¹ = H, OMe, Me, F; R² = H, Me, Ph, CF₃, C(O)Me, C(O)OMe; R¹ R² = -CH=CH-CH=CH-; R³ = H, Me, OMe, CF₃, Cl, C(O)OMe; R² R³ = -CH=CH-CH=CH-) with aryl (pseudo)halides R⁴X (R⁴ = Ph, 2H-1,3-benzodioxol-5-yl, naphthalen-2-yl, etc.; X = I, Cl, Br, OTf), which operates at ambient temperature with broad substrate scopes and excellent compatibility of functionalities was presented. The key to success of this strategy is the efficient generation of active catalytic species via photo-induced ligand dissociation The choices of the bases and solvents also have significant influence on the catalytic efficiency. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Related Products of 68716-49-4).

2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. The most common reactions of alcohols can be classified as oxidation, dehydration, substitution, esterification, and reactions of alkoxides.Related Products of 68716-49-4

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Asymmetric metal free β-boration of α,β-unsaturated imines assisted by (S)-MeBoPhoz was written by La Cascia, Enrico;Sanz, Xavier;Bo, Carles;Whiting, Andrew;Fernandez, Elena. And the article was included in Organic & Biomolecular Chemistry in 2015.Related Products of 1214264-88-6 This article mentions the following:

The adduct [MeO → Bpin-Bpin]^– efficiently mediates the β-boration of α,β-unsaturated imines formed in situ. The use of chiral phosphines as additives, and in particular the chiral phosphine (S)-MeBoPhoz (I), enables the catalytic asym. reaction to proceed with higher enantioselectivity than the analog Cu(I) mediated reaction. Reaction of PhCH:CHC(O)CH₃/mol. sieves/THF with benzhydrylamine at room temperature followed by addition of bis(pinacolato)diboron/NaO^tBu (9 mol%)/I under Ar at 70° to give 3-(benzylamino)-1-phenylbutan-1-ol in 59% isolated yield. In the experiment, the researchers used many compounds, for example, 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6Related Products of 1214264-88-6).

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine (cas: 1214264-88-6) 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.Related Products of 1214264-88-6

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chemo- and Stereoselective Synthesis of Fluorinated Amino Alcohols through One-pot Reactions using Alcohol Dehydrogenases and Amine Transaminases was written by Gonzalez-Martinez, Daniel;Gotor, Vicente;Gotor-Fernandez, Vicente. And the article was included in Advanced Synthesis & Catalysis in 2020.SDS of cas: 49669-14-9 This article mentions the following:

A series of amino alcs. have been prepared in a chemo-, diastereo- and enantioselective fashion starting from the corresponding (het)aryl diketones, avoiding tedious chem. protection and deprotection steps. Different alc. dehydrogenases have been able to selectively reduce the more reactive trifluoroacetyl groups under optimized conditions, while amine transaminases catalyzed the biotransamination of the less hindered acetyl groups. Based on the different reactivity of the acetyl and trifluoroacetyl groups, the design of sequential and concurrent cascades was investigated. The proper selection of the enzymes permits the synthesis of amino alc. stereoisomers in high to excellent yields (86->99% conversion) and remarkable stereocontrol (up to >99% de and >99% ee) using an aqueous medium and mild reaction conditions. In the experiment, the researchers used many compounds, for example, 2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine (cas: 49669-14-9SDS of cas: 49669-14-9).

2-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridine (cas: 49669-14-9) 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. 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: 49669-14-9

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Redox-neutral ortho-C-H amination of pinacol arylborates via palladium(II)/norbornene catalysis for aniline synthesis was written by Chen, Shuqing;Wang, Peng;Cheng, Hong-Gang;Yang, Chihui;Zhou, Qianghui. And the article was included in Chemical Science in 2019.Computed Properties of C12H16BBrO2 This article mentions the following:

A palladium(II)/norbornene cooperative catalysis enabled redox-neutral ortho-C-H amination of pinacol aryl- or heteroarylborates for the synthesis of structurally diverse anilines was reported. The method was scalable, robust (tolerance of air and moisture), phosphine ligand-free and compatible with a wide range of functionalities. These practical features made this reaction amenable for industry. A plethora of synthetically very useful halogenated anilines which often cannot be prepared via other transition-metal-catalyzed aminations were readily produced using this method. Particularly, the orthogonal reactivity between pinacol arylborates and aryl iodides was demonstrated. Preliminary deuterium-labeling studies revealed a redox-neutral ipso-protonation mechanism of this process, which will surely inspire the future development of this field. Overall, the exceptionally broad scope (47 examples) and reliability of this procedure, together with the wide availability of pinacol arylborates made this chem. a valuable addition to the existing methods for aniline synthesis. In the experiment, the researchers used many compounds, for example, 2-(4-Bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 68716-49-4Computed Properties of C12H16BBrO2).

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. 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 C12H16BBrO2

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts