Month: October 2022

Abe, Takumi; Noda, Kenta; Sawada, Daisuke published the artcile< Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions>, HPLC of Formula: 21667-62-9 , the main research area is indolylacetamide preparation; ammonium hemiaminal acetonitrile alkylation oxygen transfer reaction.

Authors introduce readily available ammonium hemiaminals as O-transfer reagents and com. available acetonitriles as a primary amide enolate precursor. The combination serves as an amide enolate equivalent, thereby providing one-pot access to α-substituted indolylacetamides I (EWG = COOMe, SO2Me, C(O)Ph, etc.; R1 = H, Ph). A broad substrate scope and good functional group tolerance as well as gram-scale synthesis make this protocol highly attractive. Mechanistic experiments suggest that the cyano group is trapped by a hydroxy group of hemiaminals en route to the desired primary amides under metal-free conditions.

Chemical Communications (Cambridge, United Kingdom) published new progress about Acetamides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, HPLC of Formula: 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Utimoto, Kiitiro; Wakabayashi, Yukio; Horiie, Takafumi; Inoue, Masaharu; Shishiyama, Yuho; Obayashi, Michio; Nozaki, Hitosi published the artcile< Cyanotrimethylsilane as a versatile reagent for introducing cyanide functionality>, Computed Properties of 6136-93-2, the main research area is cyanotrimethylsilane cyanation hydrocyanation; ketone cyanotrimethylsilane; acetal cyanotrimethylsilane; ortho ester cyanotrimethylsilane; sugar cyanotrimethylsilane; nitrile.

Me3SiCN adds to some α,β-unsaturated ketones in a conjugate manner under the catalytic action of Lewis acids such as Et3Al, AlCl3, and SnCl2. Hydrolysis of the products gives β-cyano ketones which are identical to the hydrocyanated products of the starting enones. Me3SiCN reacts with acetals and ortho esters under the catalytic action of SnCl2 or BF3·OEt2 affording 2-alkoxy- and 2,2-dialkoxyalkanenitriles. Application of the reaction to O-protected β-D-ribofuranoses gives selectively β-D-ribofuranosyl cyanide in excellent yield.

Tetrahedron published new progress about Acetals Role: RCT (Reactant), RACT (Reactant or Reagent). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Computed Properties of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Stambouli, Abdelhamid; Hamedi-Sangsari, Farid; Amouroux, Roger; Chastrette, Francine; Blanc, Alain; Mattioda, Georges published the artcile< 2,2-Dialkoxyethanals, bifunctional synthons with two carbons: preparation by acetalization of glyoxal and some synthetic applications>, COA of Formula: C6H11NO2, the main research area is ethanol dialkoxy preparation reaction; acetaldehyde dialkoxy preparation reaction; glyoxal monoacetalization alc.

Treatment of 40% aqueous OHCCHO or its solid trimer with a large excess of ROH (R = Me, Et, Pr, Me2CH, Bu, Me2CHCH2, cyclohexyl, allyl) in the presence of a sulfonic acid resin or Zr(SO4)2 followed by NaHCO3 gave 50-70% (RO)2CHCHO (I; same R) and only 10-20% (RO)2CHCH(OR)2. I (R = Et) was transformed into a variety of derivatives

Bulletin de la Societe Chimique de France published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, COA of Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Elmaaty, Tarek Abou; Sofan, Mamdouh; Kosbar, Tamer; Elsisi, Hanan; Negm, Ilham published the artcile< Green Approach to Dye PET and Nylon 6 Fabrics with Novel Pyrazole Disperse Dyes under Supercritical Carbon Dioxide and Its Aqueous Analogue>, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is polyethylene terephthalate nylon fabric pyrazole disperse dye; supercritical carbon dioxide green chem color property.

The development of a water-free dyeing process for synthetic fabrics is of great importance for the textile industry due to environmental and economic reasons. In this study, a series of novel 3-(3-chlorophenyl)-l-phenyl-4-(diazenyl derivatives)-lH-pyrazol-5-amine dyes were specifically synthesized for use with supercritical carbon dioxide. The new dyes were characterized by MS, IR, and NMR spectral data, and the results were found to be in good agreement with the proposed structures. The new dye stuffs were applied to dye polyester and nylon 6 fabrics under supercritical carbon dioxide and aqueous media. The color uptake expressed through the color strength (K/S) was assessed, and the values obtained showed that the dyeing of polyester and nylon 6 fabrics using the scCO2 method was significantly better than that using the aqueous method. The fastness properties of all the dyed fabrics were evaluated and exhibited excellent results. Raman micro spectroscopy indicated conclusively that the dye absorbance took place through all layers of the fabrics. Elimination of water and its costly processing can now be achieved in the dyeing of synthetic fabrics.

Fibers and Polymers published new progress about Anionic dispersants (Dispex). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Recommanded Product: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wang, Le; Wang, Gary T.; Wang, Xilu; Tong, Yunsong; Sullivan, Gerry; Park, David; Leonard, Nicholas M.; Li, Qun; Cohen, Jerry; Gu, Wen-Zhen; Zhang, Haiying; Bauch, Joy L.; Jakob, Clarissa G.; Hutchins, Charles W.; Stoll, Vincent S.; Marsh, Kennan; Rosenberg, Saul H.; Sham, Hing L.; Lin, Nan-Horng published the artcile< Design, Synthesis, and Biological Activity of 4-[(4-Cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles as Potent and Selective Farnesyltransferase(FTase) Inhibitors>, Recommanded Product: Methyl 5-cyano-2-methylbenzoate, the main research area is farnesylation Ras protein cyano aryl benzyloxy methylimidazolylmethyl benzonitrile preparation; benzamide cyano cyanophenyl methylimidazolylmethoxymethyl preparation farnesyltransferase inhibitor; farnesyltransferase inhibitor cyano aryl benzyloxy methylimidazolylmethyl benzonitrile preparation; pharmacophore farnesyltransferase inhibitor cyano aryl benzyloxy methylimidazolylmethyl benzonitrile preparation; crystal structure cyanophenyl methylimidazolylmethoxymethyl biphenylcarbonitrile farnesyltransferase complex preparation; mol structure cyanophenyl methylimidazolylmethoxymethyl biphenylcarbonitrile farnesyltransferase complex preparation.

A novel series of 4-[(4-cyano-2-arylbenzyloxy)-(3-methyl-3H-imidazol-4-yl)methyl]benzonitriles have been synthesized as selective farnesyltransferase inhibitors using a structure-based design. X-ray cocrystal structures of compound 6-[[(1R)-(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl]-3′-methoxy[1,1′-biphenyl]-3-carbonitrile-FTase-HFP and A313326-FTase-HFP confirmed our initial design. The decreased interaction between the aryl groups and Ser 48 in GGTase-I binding site could be one possible reason to explain the improved selectivity for this new series of FTase inhibitors. Medicinal chem. efforts led to the discovery of 3-cyano-6-[[(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl]-N-phenylbenzamide (I) with potent cellular activity (EC50 = 3.5 nM) and outstanding pharmacokinetic profiles in dog (96% bioavailable, 18.4 h oral t1/2, and 0.19 L/(h·kg) plasma clearance).

Journal of Medicinal Chemistry published new progress about Crystal structure. 103261-68-3 belongs to class nitriles-buliding-blocks, and the molecular formula is C10H9NO2, Recommanded Product: Methyl 5-cyano-2-methylbenzoate.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhou, Chao; Diao, Pinhui; Li, Xiaoji; Ge, Yanqin; Guo, Cheng published the artcile< Facile photochemical synthesis of α-ketoamides and quinoxalines from amines and benzoylacetonitrile under mild conditions>, Computed Properties of 21667-62-9, the main research area is acyl acetonitrile amine photochem oxidative coupling reaction; ketoamide preparation; phenylenediamine acyl acetonitrile photochem cyclocondensation reaction; arylquinoxaline carbonitrile preparation.

A selective protocol for the synthesis of either α-ketoamides or quinoxaline derivatives under the same reaction conditions was achieved simply by varying substitution number of amino-groups. The method features metal-free, room temperature and broad substrate scope as well as no extra oxidant. This process applied to various substituent groups and provided products in moderate to good yield. Finally, a rational mechanism was proposed.

Chinese Chemical Letters published new progress about Amides, oxo Role: SPN (Synthetic Preparation), PREP (Preparation). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Computed Properties of 21667-62-9.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Gore, Babasaheb Sopan; Kuo, Chiao-Ying; Garkhedkar, Amol Milind; Chang, Yu-Lun; Wang, Jeh-Jeng published the artcile< Metal-Free Solvent/Base-Switchable Divergent Synthesis of Multisubstituted Dihydrofurans>, Name: 3-(3-Chlorophenyl)-3-oxopropanenitrile, the main research area is ketonitrile cyclization; dihydropyran preparation.

A general protocol for the synthesis of multisubstituted 2,3-dihydrofuran-2-carbonitriles and 4,5-dihydrofuran-3-carbonitriles was demonstrated under a metal-free regime with the same oxidant, TBHP. By simply switching the reaction solvent and base, the reaction proceeds via two pathways. An unexpected -CN group migration rearrangement and hydroxylation have occurred in nonpolar and polar solvents, resp., under the reported conditions. Furthermore, the source of the hydroxyl group and hydrogen in the reaction is indirectly confirmed with isotope labeling studies.

Organic Letters published new progress about Crystal structure. 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Name: 3-(3-Chlorophenyl)-3-oxopropanenitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mass, Olga; Lindsey, Jonathan S. published the artcile< A trans-AB-Bacteriochlorin Building Block>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is bacteriochlorin preparation dihydrodipyrrin self condensation bromination.

Synthetic bacteriochlorins are of interest for fundamental studies in photochem. because of their strong absorption in the near-IR spectral region and close similarity with natural bacteriochlorophylls. A de novo route to 5-methoxybacteriochlorins entails self-condensation of a dihydrodipyrrin-acetal, which in turn is prepared from a 2-(2-nitroethyl)pyrrole species and an α,β-unsaturated ketone-acetal (e.g., 1,1-dimethoxy-4-methylpent-3-en-2-one). Here, four new results are reported concerning the synthesis of substituted bacteriochlorins. First, a new, scalable route to 1,1-dimethoxy-4-methylpent-3-en-2-one removes a significant previous impediment to the overall route. Second, the new route was employed to gain access to new α,β-unsaturated ketones and corresponding dihydrodipyrrins bearing alternative substituents in place of the dimethoxy unit. Third, a dihydrodipyrrin bearing a 1,3-dioxolan-2-yl moiety afforded the bacteriochlorin (30% yield) containing a 2-hydroxyethoxy substituent at the 5-position. Fourth, subsequent bromination proceeded regioselectively at the 15-position to give a trans-(5,15)-AB-bacteriochlorin building block I. The linear 5,15-substitution pattern is attractive for a number of mol. designs. The results taken together afford deeper understanding of the scope and limitations of the de novo route and also advance the capabilities for tailoring synthetic bacteriochlorins.

Journal of Organic Chemistry published new progress about Autocondensation reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Wurz, Gerald; Hofer, Otmar; Greger, Harald published the artcile< Structure and synthesis of phenaglydon, a new quinolone derived phenanthridine alkaloid from Glycosmis cyanocarpa>, Safety of 2-Chloro-4-methylbenzonitrile, the main research area is phenaglydon phenanthridine alkaloid Glycosmis structure; schinifoline Glycosmis.

A novel quinolone derived alkaloid of the phenanthridine type, phenaglydon (I), has been isolated from the lipophilic leaf extract of Glycosmis cyanocarpa (Rutaceae) together with schinifoline (II), a prenylated 2-quinolinone characterized by a diene grouping in the side chain. Both structures have been elucidated on spectroscopic evidence. In the case of phenaglydon the proposed structure has addnl. been confirmed by synthesis. The co-occurrence of these alkaloids suggests close biogenetic connections between the two compounds

Natural Product Letters published new progress about Glycosmis cyanocarpa. 21423-84-7 belongs to class nitriles-buliding-blocks, and the molecular formula is C8H6ClN, Safety of 2-Chloro-4-methylbenzonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Erickson, John G.; Montgomery, W. H.; Rorso, Ole published the artcile< Dialkoxyalkanenitriles. III. Hydrogenation to α-amino acetals>, COA of Formula: C6H11NO2, the main research area is .

The appropriate 2,2-dialkoxyalkanenitrile, solvent, and Raney Ni (and NH3 if used) pressured in an autoclave with stirring with about 100 atm. H, the mixture heated until H absorption was observed, held at this temperature, cooled when the H absorption ceased, centrifuged, and distilled gave the corresponding amino acetals. (MeO)2CHCN (I) (0.50 mol) in 80 cc. dioxane hydrogenated in the presence of 1.0 mol NH3 at 75-90° and 130 atm. yielded 38% H2NCH2CH(OMe)2 (II), b768 139.5°, f.p. below -78°, d25 0.9676, nD25 1.4144. A similar run in 80 cc. methylal at 75-80° and 135 atm. yielded 56% II; in 80 cc. cyclohexane at 80-90° and 87 atm. the yield was 67%. (EtO)2CHCN (III) (0.39 mol) in 80 cc. EtOH and 0.7 mol NH3 gave at 75-125° and 197 atm. 10% H2NCH2CH(OEt)2 (IV), b769 163°, f.p. below -78°, d25 0.9108, nD25 1.4142. A similar run in 75 cc. methylal with 0.8 mol NH3 at 75-80° and 197 atm. gave 85% IV. III (1.16 mol) and 2.3 mol NH3 in 240 cc. cyclohexane gave at 75-90° and 100 atm. 87% IV; a similar run in 275 cc. cyclohexane without NH3 at 75-80° and 100 atm. gave 67% IV and 13% HN[CH2CH(OEt)2]2, b1 86°, f.p. -30°, d25 0.9419, nD25 1.4250. (BuO)2CHCN (0.27 mol) and 0.5 mol NH3 in 85 cc. cyclohexane gave at 75-80° and 87 atm. 67% H2NCH2CH(OBu)2, b17 118°, b2 78° f.p. below -78°, d25 0.8835, nD25 1.4274. (MeO)2C(CN)Me (0.83 mol) and 3.0 mol NH3 in 300 cc. cyclohexane gave at 75-115° and 122 atm. 88% H2NCH2C(OMe)2Me, b751 146°, f.p. -70°, d25 0.9620, nD25 1.4220. (EtO)2C(CN)Ph (0.35 mol) and 1.5 mol NH3 in 40 cc. cyclohexane yielded at 100-50° and 163 atm. 71% H2NCH2C(OEt)2Ph, b0.5 68°, sets at -40° to a hard glass, d25 1.0050, nD25 1.4950.

Journal of the American Chemical Society published new progress about Acetals. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, COA of Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts