Tag: M.W=150-200

Ma, Xufeng published the artcileMixed Alkyl/Aryl Diphos Ligands for Iron-Catalyzed Negishi and Kumada Cross Coupling Towards the Synthesis of Diarylmethane, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is ChemCatChem (2021), 13(24), 5134-5140, database is CAplus.

Mixed alkyl/aryl diphos ligands have been prepared and their application in iron-catalyzed cross coupling of benzylic chlorides with diaryl zinc (Negishi) or aryl Grignard reagents (Kumada) towards the synthesis of diarylmethane has been evaluated. The iron-diphos catalytic system exhibited the enhanced activity and selectivity in the two coupling reactions. The electron-rich mixed PPh₂/PCy₂ ligands outperformed their sym. PPh₂ congeners, and led to decreased homocoupling byproduct formation. It indicates that the electronic effect of the ligands plays an important role in the catalytic performance. The Fe catalyst bearing an electron-rich PCy₂ substituent and a sterically demanding tert-Bu on ethene backbone exhibited the best catalytic performance and good functional group tolerance in the two cross coupling reactions.

ChemCatChem 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

Cao, Xu published the artcileSynthesis and anticonvulsant activity evaluation of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]thiazin-1-ones in various murine experimental seizure models, Recommanded Product: 2-(Chloromethyl)benzonitrile, the publication is Medicinal Chemistry Research (2014), 23(4), 1829-1838, database is CAplus.

A novel series of 7-alkoxy-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]-thiazin-1-ones have been synthesized and tested for their anticonvulsant activity using the maximal electroshock (MES) method. The majority of the compounds prepared were effective in the MES screens at a dose level of 100 mg/kg. Of the compounds tested, the most promising was 7-[(4-fluorobenzyl)oxy]-2,4-dihydro-1H-[1,2,4]-triazolo[4,3-d][1,4]-benzothiazin-1-one (I), which showed an ED₅₀ value of 9.2 mg/kg in the MES test in mice. Furthermore, the compound exhibited a PI value of 15.4 which was superior to the standard drug carbamazepine (PI value of 6.4). As well as demonstrating the anti-MES efficacy of compound I, its potency against seizures induced by pentylenetetrazole, 3-mercaptopropionic acid, and bicuculline were also established, with the results suggesting that several different mechanisms of action might be involved in its anticonvulsant activity, including the inhibition of voltage-gated ion channels and the modulation of GABAergic activity.

Medicinal Chemistry 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, Recommanded Product: 2-(Chloromethyl)benzonitrile.

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

Liang, Zheng-Ming published the artcile1α,2α-Epoxy-3β-hydroxy oleanolic acid derivatives regulation of the metabolism, haemolysis and β-lactamase gene expression in vitro and their structure-microbicidal activity relationship, COA of Formula: C8H6ClN, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(16), 3870-3875, database is CAplus and MEDLINE.

Oleanolic acid (OA), one of the major pentacyclic triterpenes abundantly present in nature, is a promising compound with various biol. activities, including anti-inflammatory, anti-ulcer, hepatoprotective, antidiabetic, fungicidal and antiparasitic properties. Therefore, a series of derivatives of 1α,2α-epoxy-3β-hydroxyoleanolic acid derivatives were designed and synthesized, and their antibacterial activities were investigated in vitro. Based on these results, the compounds with antibacterial activity were screened by RT-PCR to determine whether they can regulate the expression of genes related to metabolism, hemolysis, and β-lactamase in vitro, and the structure-microbicidal activity relationship of each compound was analyzed. Our study shows that some of the modifications in the synthetic compounds, such as the introduction of an ortho-cyano-substituted benzyl group and a short chain alkyl ester at the 28-carboxyl, as well as the introduction of an acetyl group at the 3-hydroxyl group of ring A, could enhance antibacterial activity. This provides basic evidence for the optimization of 1α,2α-epoxy-3β-hydroxyoleanolic acid derivatives The antibacterial mechanism of the active OA derivatives appears to involve the regulation of expression of metabolism-associated genes in Escherichia coli, hemolysis-associated genes in Bacillus subtilis, metabolism-related genes in Klebsiella pneumonia and β-lactamase-associated genes in Acinetobacter baumannii. Some OA derivatives were bactericidal to three of the strains and appeared to regulate gene expression associated with metabolism, hemolysis, and β-lactamase in vitro. These newly designed OA derivatives possess unique antibacterial activities and may be potentially useful for prophylactic or therapeutic intervention of bacterial infections.

Bioorganic & Medicinal Chemistry Letters 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, COA of Formula: C8H6ClN.

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

Zhang, Xiao published the artcileDesign, Synthesis, and Synergistic Activity of Eight-Membered Oxabridge Neonicotinoid Analogues, Category: nitriles-buliding-blocks, the publication is Journal of Agricultural and Food Chemistry (2021), 69(10), 3005-3014, database is CAplus and MEDLINE.

Insecticide synergists are sought-after due to their potential in improving the pesticide control efficacy with a reduced dose of an active ingredient. We previously reported that a cis-configuration neonicotinoid (IPPA08) exhibited specific synergistic activity toward neonicotinoid insecticides. In this study, we synthesized a series of structural analogs of IPPA08 by converting the pyridyl moiety of IPPA08 into Ph groups, via facile double-Mannich condensation reactions between nitromethylene compounds and glutaraldehyde. All of the oxabridged neonicotinoid compounds were found to increase the toxicity of imidacloprid against Aphis craccivora. Notably, compound (I) at 0.75 mg/L lowered the LC₅₀ value of imidacloprid against A. craccivora by 6.54-fold, while a 3.50-fold reduction of the LC₅₀ value was observed for IPPA08. The results of bee toxicity test showed that compound I display selectivity in its effects on imidacloprid toxicity against the honey bee (Apis mellifera L.). In summary, replacing the pyridyl ring with a Ph ring was a viable approach to obtain a novel synergist with oxabridged moiety for neonicotinoid insecticides.

Journal of Agricultural and Food Chemistry 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 C2H4ClNO, Category: nitriles-buliding-blocks.

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

Wu, Lulu published the artcileSynthesis of Optically Active 2H-Thiopyrano[2,3-b]quinolines with Three Contiguous Stereocenters via an Organocatalytic Asymmetric Tandem Michael-Henry Reaction, SDS of cas: 5153-73-1, the publication is Advanced Synthesis & Catalysis (2013), 355(6), 1053-1057, database is CAplus.

Optically active 2H-thiopyrano[2,3-b]quinolines with three contiguous stereocenters were synthesized via a chiral bifunctional squaramide-catalyzed tandem thia-Michael-Henry reaction between 2-mercaptoquinoline-3-carboxaldehydes and nitroolefins. The reactions proceeded in high yields to give the title compounds, e.g., I, with high levels of diastereo- and enantioselectivity (up to >99/1 dr and >99% ee, resp.).

Advanced Synthesis & Catalysis 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 C7H8BClO2, SDS of cas: 5153-73-1.

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

Singh, Shivendra published the artcileRapid access of 2,3,4-trisubstituted-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole derivatives via one-pot three component catalytic reaction, Synthetic Route of 5153-73-1, the publication is Tetrahedron Letters (2012), 53(45), 6087-6090, database is CAplus.

A simple, green, and efficient one-pot three component strategy for the synthesis of 2-aryl-3-nitro-4-hydroxy-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoles I [R = Boc, EtO₂C; R¹ = Ph, 4-MeC₆H₄, 2-ClC₆H₄, etc.; R² = H, Me] has been achieved by the combination of N-protected-2-chloro-3-formylindoles, sodium hydrosulfide with β-nitrostyrenes R¹CH:C(R²)NO₂ at room temperature in ethanol using DABCO as a catalyst. Furthermore, high enantio- and diastereoselectives’ syntheses of title compounds have been achieved for the first time using cupreidine (5 mol %) as catalyst, providing good to excellent yields.

Tetrahedron Letters 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 C10H15ClO3S, Synthetic Route of 5153-73-1.

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

Fisher, D. E. published the artcileFate of Banvel T, ioxynil, Tordon, and trifluralin in the dairy cow, Computed Properties of 3336-34-3, the publication is Journal of Dairy Science (1965), 48(12), 1711-15, database is CAplus.

The metabolic fate of 5 ppm. of 4 orally administered herbicides was determined by gas chromatography on neutron activation analysis of total I in the feces, urine, rumen contents, and milk of dairy cows. No residues of Banvel T (2-methoxy-3,5,6-trichlorobenzoic acid), ioxynil (3,5-diiodo-4-hydroxybenzonitrile), or trifluralin (α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine) were found in the milk. Banvel T and Tordon (4-amino-3,5,6-trichloropicolinic acid) were eliminated unchanged in the urine. No ioxynil or a possible metabolite, 3,5-diiodo-4-hydroxybenzoic acid, was found in the milk, urine, or feces by gas chromatography, but neutron activation analysis of total I indicated that substantial amounts of ioxynil and a metabolite, possibly 3-iodo-4-hydroxybenzonitrile, were present. Trifluralin completely disappeared during 24 hrs. in an artificial rumen, possibly due to nitro reduction

Journal of Dairy Science published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Computed Properties of 3336-34-3.

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

Szczesniak, Piotr published the artcileAsymmetric Synthesis of Cyclic Nitrones via Organocatalytic Michael Addition of Aldehydes to Nitroolefins and Subsequent Reductive Cyclization., HPLC of Formula: 5153-73-1, the publication is ChemistrySelect (2017), 2(9), 2670-2676, database is CAplus.

A direct approach to the synthesis of optically active five-membered cyclic nitrones I [R¹ = H, Me, OBn, etc., R² = H, Et, Ph, etc.; R¹R² = (CH₂)₄, (CH₂)₅; R³ = Ph, 2-naphthyl, 2-thienyl, etc.] was described. The presented strategy was based on organocatalytic Michael addition of aldehydes to trans-nitroalkenes to afford γ-nitroaldehydes II and subsequent reductive cyclization to form 4-substituted-3-(aryl)-3,4-dihydro-2H-pyrrole-1-oxides I. The developed methodol. was successfully applied to the asym. synthesis of Methdilazine.

ChemistrySelect 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 C8H17Br, HPLC of Formula: 5153-73-1.

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

Ooi, Takashi published the artcileZr(OtBu)₄ as a new promoter for the Meerwein-Ponndorf-Verley alkynylation and cyanation of aldehydes, Product Details of C8H6ClNO, the publication is Synlett (2000), 69-70, database is CAplus.

Zr(OCMe₃)₄ can serve as an effective promoter for the Meerwein-Ponndorf-Verley alkynylation of aldehydes, and it was found to be particularly attractive in the Meerwein-Ponndorf-Verley cyanation.

Synlett 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 C8H6ClNO, Product Details of C8H6ClNO.

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

Feng, Huan-Xi published the artcileAn Efficient One-Pot Approach to the Construction of Chiral Nitrogen-Containing Heterocycles under Mild Conditions, Related Products of nitriles-buliding-blocks, the publication is Organic Letters (2015), 17(15), 3794-3797, database is CAplus and MEDLINE.

A new, general, and practical procedure for the highly enantioselective synthesis of functionalized nitrogen-containing heterocycles, e.g., I, has been developed. The simple cyclic hemiaminals were directly catalyzed for the first time as nucleophiles in an enamine-based asym. conjugate addition reaction. The practical approach recycles the catalyst and solvent which make it possible for large-scale and diversity-oriented chem. production

Organic Letters 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, Related Products of nitriles-buliding-blocks.

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