Tag: M.W=150-200

Li, Si-Yuan published the artcilePractical copper-catalyzed chloronitration of alkenes with TMSCl and guanidine nitrate, Quality Control of 5153-73-1, the publication is Organic Chemistry Frontiers (2020), 7(17), 2449-2455, database is CAplus.

A novel and practical chloronitration of alkenes in the presence of easily available TMSCl and guanidine nitrate was developed by using cheap copper sulfate pentahydrate as the catalyst. A variety of vic-chloronitro compounds were directly synthesized in good to excellent yields on up to 100 mmol scale under mild reaction conditions, and the resulting products could be smoothly transformed into the corresponding nitroalkenes and diverse nitro compounds bearing a vicinal nucleophilic “C”, “N” or “S” unit.

Organic Chemistry Frontiers published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Quality Control of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Chen, Yi-Hung published the artcilePreparation and Application of Solid, Salt-Stabilized Zinc Amide Enolates with Enhanced Air and Moisture Stability, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Angewandte Chemie, International Edition (2017), 56(16), 4612-4616, database is CAplus and MEDLINE.

The treatment of various N-morpholino amides with TMPZnCl·LiCl (TMP=2,2,6,6-tetramethylpiperidyl) and Mg(OPiv)₂ in THF at 25 °C provides solid zinc enolates with enhanced air and moisture stability (t_1/2 in air: 1-3 h) after solvent evaporation These enolates undergo Pd- and Cu-catalyzed cross-couplings with (hetero)aryl bromides as well as allylic and benzylic halides. The arylated N-morpholino amides were converted into various ketones by LaCl₃·2 LiCl mediated acylation with Grignard reagents. The new, solid enolates were used to prepare a potent anti-breast-cancer drug candidate in six steps and 23 % overall yield.

Angewandte Chemie, International Edition published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Recommanded Product: 2-(Chloromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Yosef, Hisham Abdallah A. published the artcileSynthesis and biological evaluation of some novel chiral carbamates and 4-imino-2- oxazolidinones derived from selected optically active cyanohydrins, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Pharma Chemica (2017), 9(16), 6-21, database is CAplus.

The reaction of tert-Bu isocyanate with the optically active cyanohydrins was accompanied with inversion of configuration giving the chiral (S)-enantiomers of the resp. carbamate derivatives On the other hand, reactions of aryl isocyanate reagents Ar-N=C=O with cyanohydrins gave the corresponding optically active 4-imino-2-oxazolidinone derivatives in the form of their S-configuration. Moreover, the same reactions were also applied for the racemic cyanohydrins to afford the corresponding carbamates and/or 4-imino-2-oxazolidinones as racemic mixtures Structures of the new products were elucidated with compatible micro anal. and spectroscopic (IR, ¹H-NMR, ¹³C-NMR and MS) measurements. The X-ray crystallog. anal. provided an efficient tool in confirming the structure and configuration of the new chiral compounds The antimicrobial activity of selected new derivatives against four bacterial species (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and two fungi (Aspergillus flavus and Candida albicans) were evaluated. Moreover, some of the new products were screened for their in-vitro antitumor activity against the human solid cancer cell lines, human carcinoma (HCT116), human hepatocellular liver carcinoma (HepG2) and human breast adenocarcinoma (MCF-7) cell lines. Generally, most of the investigated compounds were showed moderate to high activities in comparison with the standard drugs. The structure-activity relationship (SAR) was also discussed.

Pharma Chemica published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C2H5BF3K, Application of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Abu-Shanab, Fathi A. published the artcileα,α-Dioxoketene dithioacetals as starting materials for the synthesis of polysubstituted pyridines, Category: nitriles-buliding-blocks, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1994), 1449-52, database is CAplus.

Reactions of 3-acetyl-4,4-bis(methylthio)but-3-en-2-one and Me 2-acetyl-3,3-bis(methylthio)-prop-2-enoate with cyanothioacetamide, cyanoacetamide, or 2-amino-1,3,3-tricyanoprop-1-ene and base, followed by treatment with acid, give polysubstituted pyridines. Further elaboration of these products leads to bicyclic systems such as thieno[2,3-b]pyridines and pyrazolo[3,4-c]pyridine and then to tricyclic systems including pyrazolo[3,4-d]thieno[2,3-b]pyridine and dipyrazolo[3,4-b:3′,4′-d]pyridine.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about 57663-05-5. 57663-05-5 belongs to nitriles-buliding-blocks, auxiliary class Fused/Partially Saturated Cycles,Tetrahydropyrimidins, name is 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile, and the molecular formula is C8H8N2OS, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Eskandariyan, Zahra published the artcileSynthesis of thioether derivatives of quinazoline-4-one-2-thione and evaluation of their antiplatelet aggregation activity, Category: nitriles-buliding-blocks, the publication is Archives of Pharmacal Research (2014), 37(3), 332-339, database is CAplus and MEDLINE.

A series of 2-(arylmethylthio)-3-phenylquinazolin-4-one derivatives have been synthesized and their antiplatelet aggregation activities were assessed against ADP and arachidonic acid-induced platelet aggregation in human plasma. Among the tested thioethers, derivative 2, 3, 5 and 16 were the most potent compounds with satisfactory IC₅₀ for inhibition of platelet aggregation induced by ADP. Anal. of global physicochem. parameters shows some correlations between activities and mol. volume and also surface area of the studied derivatives

Archives of Pharmacal Research published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Category: nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Guerrero-Corella, Andrea published the artcile2-Hydroxybenzophenone as a Chemical Auxiliary for the Activation of Ketiminoesters for Highly Enantioselective Addition to Nitroalkenes under Bifunctional Catalysis, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Angewandte Chemie, International Edition (2018), 57(19), 5350-5354, database is CAplus and MEDLINE.

An organocatalytic system is presented for the Michael addition of monoactivated glycine ketimine ylides with a bifunctional catalyst. The ketimine bears an ortho hydroxy group, which increases the acidity of the methylene hydrogen atoms and enhances the reactivity, thus allowing the synthesis of a large variety of α,γ-diamino acid derivatives with excellent stereoselectivity.

Angewandte Chemie, International Edition published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Diosdado, Saioa published the artcileCatalytic Enantioselective Synthesis of Tertiary Thiols From 5H-Thiazol-4-ones and Nitroolefins: Bifunctional Ureidopeptide-Based Bronsted Base Catalysis, Computed Properties of 5153-73-1, the publication is Angewandte Chemie, International Edition (2013), 52(45), 11846-11851, database is CAplus and MEDLINE.

The synthesis of the target compounds was achieved using urea-peptide analogs as catalysts (Bronsted acids). A reaction of amino acids (L-valine, 3-methyl-L-valine) with (8α,9S)-6′-methoxycinchonan-9-amine (epiquinine, cinchona alkaloid derivative) provided the above-mentioned urea-peptide analogs. These catalysts were applied in a Michael reaction of thiazolone derivatives with (nitro)alkenes. A reaction of 2-mercaptobutanoic acid, 2-(mercapto)octanoic acid, α-(mercapto)benzenepropanoic acid with nitriles provided 4-thiazolol derivatives (4-thiazolone derivatives). The title compounds thus formed included a thiazolone nitroalkane derivative (I) and related substances, quinoline derivatives, naphthalene derivatives, etc.

Angewandte Chemie, International Edition published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Computed Properties of 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Izquierdo, Joseba published the artcileEnantioselective Synthesis of 5,5-Disubstituted Hydantoins by Bronsted Base/H-Bond Catalyst Assisted Michael Reactions of a Design Template, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Chemistry – A European Journal (2018), 24(28), 7217-7227, database is CAplus and MEDLINE.

A new method for the enantioselective synthesis of 5,5-disubstituted (quaternary) hydantoins, e.g., I was developed on the basis of an organocatalytic Michael reaction approach involving the use of 2-benzylthio-3,5-dihydroimidazol-4-ones as key hydantoin surrogates. The method is general with respect to the substitution pattern at the hydantoin N¹ (alkyl, aryl, acyl), N³ (aryl), and C⁵ (linear/branched alkyl, aryl) positions and affords essentially single diastereomeric products with enantioselectivities higher than 95 % ee in most cases. Among the bifunctional Bronsted base/H-bond catalysts examined, a known squaramide-tertiary amine catalyst II and a newly prepared squaramide-tertiary amine catalyst III provide the highest selectivity so far with either nitroolefins or vinyl ketones as the acceptor components. Kinetic measurements support a first-order rate dependence on both reaction partners, the donor template and the Michael acceptor, whereas competitive ¹H NMR spectroscopy experiments reveal the high ability of the template for catalyst binding.

Chemistry – A European Journal published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Chen, Weiqiang published the artcileThe Cyclohexa-2,5-dienyl Group as a Placeholder for Hydrogen: Organocatalytic Michael Addition of an Acetaldehyde Surrogate, SDS of cas: 5153-73-1, the publication is Chemistry – A European Journal (2020), 26(66), 15126-15129, database is CAplus and MEDLINE.

An aldehyde with a cyclohexa-2,5-dienyl group in the α-position is introduced as a storable surrogate of highly reactive acetaldehyde. The cyclohexa-2,5-dienyl unit is compatible with an enantioselective Michael addition to nitroalkenes promoted by a Hayashi-Jorgensen catalyst and can be removed by a boron Lewis acid mediated C-C bond cleavage. The robust two-step sequence does not require a large excess of the aldehyde component that is typically needed when directly using acetaldehyde.

Chemistry – A European Journal published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, SDS of cas: 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Kang, Dongwei published the artcileSynthesis and preliminary antiviral activities of piperidine-substituted purines against HIV and influenza A/H1N1 infections, Product Details of C8H6ClN, the publication is Chemical Biology & Drug Design (2015), 86(4), 568-577, database is CAplus and MEDLINE.

We have developed a series of N²-(1-(substituted-aryl)piperidin-4-yl)-N⁶-mesityl-9H-purine-2,6-diamine derivatives as potent antiviral agents. Preliminary biol. evaluation indicated that nearly half of them possessed remarkable HIV inhibitory potencies in cellular assays. In particular, FZJ13 appeared to be the most notable one, which displayed anti-HIV-1 activity compared to 3TC. Moreover, an unexpected finding was that FZJ05 displayed significant potency against influenza A/H1N1 (strain A/PR/8/34) in Madin-Darby canine kidney cells with EC₅₀ values much lower than those of ribavirin, amantadine, and rimantadine. The results suggest that these novel purine derivatives have the potential to be further developed as new therapeutic agents against HIV-1 or influenza virus.

Chemical Biology & Drug Design published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Product Details of C8H6ClN.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts