Tag: M.W=150-200

Liu, Bei-Bei published the artcileAqueous Reaction of Alcohols, Organohalides, and Odorless Sodium Thiosulfate under Transition-Metal-Free Conditions: Synthesis of Unsymmetrical Aryl Sulfides via Dual C-S Bond Formation, Synthetic Route of 612-13-5, the publication is Journal of Organic Chemistry (2017), 82(19), 10174-10180, database is CAplus and MEDLINE.

A transition-metal-free process for the synthesis of unsym. aryl sulfides via dual C-S bond formation by a one-pot three-component reaction of alcs., organohalides, and odorless sodium thiosulfate in water was developed. In addition, the aryl sulfides could also be prepared by the reaction of the corresponding alcs. and Bunte salts under the identical conditions. This protocol provides a green and efficient manner for the construction of various unsym. aryl sulfides.

Journal of Organic 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 C8H6ClN, Synthetic Route of 612-13-5.

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

Zuck, Donald A. published the artcileStabilization of vitamin B₁₂. II. α-Hydroxy nitriles, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Journal of Pharmaceutical Sciences (1963), 63-6, database is CAplus.

α-Hydroxy nitriles and esters of mandelonitrile were effective stabilizers of I except under conditions of prolonged exposure to ultraviolet light when decomposition was more rapid than in the controls.

Journal of Pharmaceutical Sciences 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 C10H11NO4, Recommanded Product: 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Khanna, Avinash published the artcileDesign, Synthesis, and Pharmacological Evaluation of Second Generation EZH2 Inhibitors with Long Residence Time, HPLC of Formula: 57663-05-5, the publication is ACS Medicinal Chemistry Letters (2020), 11(6), 1205-1212, database is CAplus and MEDLINE.

Histone methyltransferase EZH2, which is the catalytic subunit of the PRC2 complex, catalyzes the methylation of histone H3K27-a transcriptionally repressive post-translational modification (PTM). EZH2 is commonly mutated in hematol. malignancies and frequently overexpressed in solid tumors, where its expression level often correlates with poor prognosis. First generation EZH2 inhibitors are beginning to show clin. benefit, and we believe that a second generation EZH2 inhibitor could further build upon this foundation to fully realize the therapeutic potential of EZH2 inhibition. During our medicinal chem. campaign, we identified 4-thiomethyl pyridone as a key modification that led to significantly increased potency and prolonged residence time. Leveraging this finding, we optimized a series of EZH2 inhibitors, with enhanced antitumor activity and improved physiochem. properties, which have the potential to expand the clin. use of EZH2 inhibition.

ACS Medicinal Chemistry Letters 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, HPLC of Formula: 57663-05-5.

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

Carpenter, K. published the artcileHerbicidal activity of halogenohydroxybenzonitriles, SDS of cas: 3336-34-3, the publication is Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent (1964), 29(3), 644-54, database is CAplus.

The activities of analogs of ioxynil (4-hydroxy-3,5-diiodobenzonitrile) (I) were compared in greenhouse experiments I applied in amounts of 0.25 kg./ha. to the leaves of seedlings, kills weed spp. belonging to the Compositae, Cruciferae, Chenopodiaceae, Polygonaceae, and Caryophyllaceae families. Replacement of one or both of the iodine atoms in I by Cl or Br influences the herbicidal spectrum, but not the general level of herbicidal activity as determined in the greenhouse. However, the number of halogens introduced and their positions in the nucleus are both critical, since the peak of activity occurs with dihalogenation in the 3- and 5-positions. Conversion of the CN group into either a CONH₂ or COOH group and changes in the position of the OH group are all detrimental to activity. Acetylation of the OH group results in no loss of activity, but methylation causes some reduction in the herbicidal activity.

Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent 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, SDS of cas: 3336-34-3.

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

Carpenter, K. published the artcileHerbicidal activity of halo hydroxybenzonitriles, Name: 2,6-Dichloro-3-hydroxybenzonitrile, the publication is Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent (1964), 29(3), 644-54, database is CAplus.

The activity of 37 specified analogs of the new herbicide ioxynil (4-hydroxy-3,5-diiodobenzonitrile) are compared in greenhouse screening experiments Ioxynil, applied to the leaves of seedlings, kills weed species belonging to the Compositae, Cruciferae, Chenopodiaceae, Polygonaceae, and Caryophyllaceae families. Replacement of one or both of the I atoms in ioxynil by Cl or Br influences the herbicidal spectrum but not the general level of herbicidal activity. However, the number of halogens introduced and their positions in the nucleus are both critical, since the peak of activity occurs with dihalogenation in the 3 and 5 positions. Conversion of the nitrile group into either the amide or carboxyl group and changes in the position of the hydroxyl group are all detrimental to activity. Acetylation of the hydroxyl group results in no loss of activity, but methylation causes some reduction of the herbicidal activity.

Mededelingen van de Landbouwhogeschool en de Opzoekingsstations van de Staat te Gent 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, Name: 2,6-Dichloro-3-hydroxybenzonitrile.

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

Barbier, Vincent published the artcileMorita-Baylis-Hillman Reactions with Nitroalkenes: A Case Study, Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is European Journal of Organic Chemistry (2015), 2015(17), 3679-3688, database is CAplus.

The use of a highly reactive super-DMAP catalyst in Morita-Baylis-Hillman (MBH) reactions of nitroalkenes with Et glyoxylate, which result in excellent conversions and short reaction times with, importantly, very low catalyst loading is reported. An extensive study of this particular reaction is presented, which examines all mechanistic and exptl. details. Several critical points were hence uncovered that include the correlation between reaction efficiency and Lewis basicity of the catalyst; the double role played by the promoter, primarily as a nucleophilic activator towards the nitroalkene, and as a Bronsted base that triggers glyoxylate depolymerization More generally, the limitations in the choice of electrophiles that can engage efficiently in MBH-type transformations are rationalized by the competition between a productive pathway and a nitroalkene polymerization process. Other aspects of this transformation, used as a case study, are presented in the light of phys. organic chem.

European Journal of Organic Chemistry 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, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Jaiswal, Pradeep Kumar published the artcileStereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael-Henry reaction: an easy access to four contiguous chiral centers, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is RSC Advances (2013), 3(27), 10644-10649, database is CAplus.

For the first time, a very simple, efficient, mild, catalytic and one-step procedure for the synthesis of a series of densely functionalized 1-methoxycarbonyl-2-aryl-3-nitro-4-hydroxy-1,2,3,4-tetrahydro-9H-carbazole derivatives was achieved by a domino Michael reaction-Henry reaction (tandem reaction) of Me 3-formyl-1H-indole-2-acetic acid esters and β-nitrostyrene derivatives using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. Furthermore, high enantioselectivity (92% enantiomeric excess) and diastereoselectivity (≤12:1 dr) were observed with a chiral organocatalyst and thus, the synthesis of the target compounds was achieved in excellent yield using 9-(benzyl)cupreidine (10 mol%) as catalyst. The title compounds thus formed included a tetrahydro(hydroxy)(nitro)(phenyl)carbazolecarboxylic acid ester derivative (I) and related substances.

RSC Advances 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, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Jaiswal, Pradeep Kumar published the artcileAn organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water, Formula: C9H6N2O2, the publication is Organic & Biomolecular Chemistry (2013), 11(48), 8410-8418, database is CAplus and MEDLINE.

A simple, mild, green, catalytic and general procedure for the direct synthesis of highly functionalized 1-methoxycarbonyl-2-aryl/alkyl-3-nitro-9H-carbazoles was achieved in water medium via a one-pot domino Michael-Henry/aromatization reaction of Me 2-(3-formyl-1H-indol-2-yl)acetates with aryl/alky-substituted β-nitroolefins under air using DABCO (30 mol%) as an organocatalyst. In addition, the bench scale synthesis can be performed without using toxic organic solvents and a biol. important new fused carbazole was prepared

Organic & Biomolecular Chemistry 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, Formula: C9H6N2O2.

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

Zhang, Sheng published the artcilePalladium-Catalyzed sp²-sp³ Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes, Category: nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (2017), 82(11), 5974-5980, database is CAplus and MEDLINE.

Palladium-catalyzed remote sp²-sp³ coupling reaction of chloromethylarenes with allyltrimethoxysilane is described in this work. The allylation reaction regioselectively occurred on the para-positions of 1-(chloromethyl)naphthalenes and benzyl chlorides to form new C(sp²)-C(sp³) bonds. The reaction proceeds smoothly under mild conditions to produce allyl arenes in moderate to excellent yields.

Journal of Organic 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 C7H5Cl2NO, Category: nitriles-buliding-blocks.

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

Zhang, Zhi-Jun published the artcileCharacterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids, Formula: C8H6ClNO, the publication is Applied Microbiology and Biotechnology (2018), 102(14), 6047-6056, database is CAplus and MEDLINE.

A nitrilase from Hoeflea phototrophica DFL-43 (HpN) demonstrating excellent catalytic activity towards benzoylacetonitrile was identified from a nitrilase tool-box, which was developed previously in our laboratory for (R)-o-chloromandelic acid synthesis from o-chloromandelonitrile. The HpN was overexpressed in Escherichia coli BL21 (DE3), purified to homogeneity by nickel column affinity chromatog., and its biochem. properties were studied. The HpN was very stable at 30-40°C, and highly active over a wide range of pH values (pH 6.0-10.0). In addition, the HpN could tolerate against several hydrophilic organic solvents. Steady-state kinetics indicated that HpN was highly active towards benzoylacetonitrile, giving a K_M of 4.2 mM and a k_cat of 170 s^-1, the latter of which is ca. fivefold higher than the highest record reported so far. A cascade reaction for the synthesis of optically pure (S)-β-phenylalanine from benzoylacetonitrile was developed by coupling HpN with an ω-transaminase from Polaromonas sp. JS666 in toluene-water biphasic reaction system using β-alanine as an amino donor. Various (S)-β-amino acids could be produced from benzoylacetonitrile derivatives with moderate to high conversions (73-99%) and excellent enantioselectivity (> 99% ee). These results are significantly advantageous over previous studies, indicating a great potential of this cascade reaction for the practical synthesis of (S)-β-phenylalanine in the future.

Applied Microbiology and Biotechnology 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 C14H26O2, Formula: C8H6ClNO.

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