Category: 5153-70-8

Shim, Jae Ho; Hong, Yeonsun; Kim, Ji Hae; Kim, Hyeon Soo; Ha, Deok-Chan published the artcile< Organocatalytic Asymmetric Michael Addition in Aqueous Media by a Hydrogen-Bonding Catalyst and Application for Inhibitors of GABAB Receptor>, SDS of cas: 5153-70-8, the main research area is organocatalytic asym Michael addition hydrogen bonding catalyst GABAB receptor.

Catalysts based on (R, R)-1,2-diphenylethylenediamine are, as chiral organic catalysts, applied to the asym. Michael addition to α, β-unsaturated nitroalkenes under neutral conditions. The role of an aqueous medium for organic catalytic activity can be reversed concerning hydrophilic-hydrophobic function depending on the reaction conditions. In this study, to provide an environmentally friendly system, the thiourea-based catalyst substituted with 3,5-(CF3)2-Ph was used in water solvents. The hydrophobic effect of the substituent provided fast reaction, high chem. yield, and mirror-image selectivity. This reaction allowed the preparation of GABAB agonists in an optically pure manner. Addnl., GABA (γ-aminobutyric acid) analogs such as baclofen and phenibut were synthesized as R-type S-type with high optical purity.

Catalysts published new progress about Asymmetry. 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, SDS of cas: 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Moreira, Natalia M.; Martelli, Lorena S. R.; de Julio, Kiyara I. R.; Zukerman-Schpector, Julio; Opatz, Till; Correa, Arlene G. published the artcile< Copper-Catalyzed One-Pot Synthesis of 3-(N-Heteroarenyl)acrylonitriles through Radical Conjugated Addition of β-Nitrostyrene to Methylazaarenes>, Electric Literature of 5153-70-8, the main research area is heteroarenylacrylonitrile preparation copper catalyst conjugated beta addition nitrostyrene methylazaarene.

A simple procedure for the copper-catalyzed synthesis of 3-(N-heteroaryl)acrylonitriles was developed. Using a combination of Lewis and Bronsted acids, this one-pot procedure undergoes via a radical conjugated addition and dehydration processes, without isolation of any intermediate, affording the acrylonitriles. This diastereoselective approach gave a broad scope of quinazoline derivatives (22 examples) with moderate to good yields and good functional-group tolerance and could be extended to other N-heterocycles such as quinolines and isoquinolines. Based on control experiments, a mechanistic proposal for this new transformation is also presented.

European Journal of Organic Chemistry published new progress about Addition reaction. 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Electric Literature of 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Genc, Hayriye Nevin; Ozgun, Ummu; Sirit, Abdulkadir published the artcile< Design, synthesis and application of chiral tetraoxacalix[2]arene[2]triazine-based organocatalysts in asymmetric Michael addition reactions>, Application In Synthesis of 5153-70-8, the main research area is aryl dimethyl nitrobutanal preparation enantioselective; isobutyraldehyde nitrostyrene Michael oxacalixarene triazine organocatalyst; Michael addition; asymmetric synthesis; organocatalysis; stereoselectivity; tetraoxacalix[2]arene[2]triazine.

A novel type of (R,S)/(S,R)-oxacalix[2]arene[2]triazine-based organocatalysts I for asym. Michael reactions is reported for the first time. Chiral subunits were attached to the heteroatom-bridged calixarom. platform by a reaction of (R)- and (S)-1-aminotetraline with tetraoxacalix[2]arene[2]triazine in both enantiomeric forms. To evaluate the catalytic efficiency of the novel organocatalysts , isobutyraldehyde reacted with various substituted and unsubstituted aromatic trans-β-nitrostyrenes (E)-RCH=CHNO2 (R = Ph, 2-bromophenyl, furan-2-yl, etc.) in THF (THF), leading to Michael adducts (S)-HC(O)C(CH3)2CH(R)CH2NO2 in excellent yields and enantioselectivites (up to 97% yield and 99% ee).

Chirality published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Application In Synthesis of 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Zhang, Kun; Jelier, Benson; Passera, Alessandro; Jeschke, Gunnar; Katayev, Dmitry published the artcile< Synthetic Diversity from a Versatile and Radical Nitrating Reagent>, Product Details of C8H6ClNO2, the main research area is nitroalkene preparation diastereoselective regioselective chemoselective; alkene nitrosuccinimide nitration ruthenium photocatalyst; nitrohydrin preparation regioselective chemoselective; ketone alkene nitrosuccinimide nitration ruthenium photocatalyst; isoxazoline preparation regioselective chemoselective; nitrosuccinimide ketone alkene dipolar cycloaddition ruthenium photocatalyst; isoxazole preparation regioselective chemoselective; alkyne nitrosuccinimide ketone dipolar cycloaddition ruthenium photocatalyst; C−H nitration; alkenes; photoredox; radicals; reaction mechanisms.

A new methodol. was described for the activation of N-nitrosuccimide for the direct synthesis of β-nitroalkenes, β-nitrohydrins, β-nitroethers, isoxazolines I [R = Me, cyclopropyl; R1 = n-heptyl, Bn, CH2OPh; R2 = H, R1R2 = (CH2)4, (CH2)9, (CH2)10C(O)(CH2)3; R3 = H, Me] and isoxazoles II [R4 = CO2Et, CH2CH2Br, cyclohexyl, etc.]. Detailed mechanistic studies strongly suggested that a mesolytic N-N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, ESR spectroscopy, direct evidence of a nitryl radical in solution by nitrone spin-trapping was observed To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C-H partners to prepare isoxazolines I and isoxazoles II was presented. This approach allowed for the formation of an in situ nitrile oxide from a ketone partner, the presence of which was detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeded in a single-operational step using a mild, regioselective and general protocol with broad chemoselectivity.

Chemistry – A European Journal published new progress about 1,3-Dipolar cycloaddition catalysts (regioselective). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Product Details of C8H6ClNO2.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Giorgianni, Giuliana; Nori, Valeria; Baschieri, Andrea; Palombi, Laura; Carlone, Armando published the artcile< Organocatalyzed Michael addition to nitroalkenes via masked acetaldehyde>, Reference of 5153-70-8, the main research area is nitroaldehyde preparation enantioselective; acetaldehyde nitroalkene Michael addition organocatalyst.

A novel and safe reaction protocol for the enantioselective enamine-catalyzed addition of acetaldehyde to nitroalkenes R1CH=CHNO2 (R1 = Bu, 4-chloropheny, 2-phenylethyl, etc.) is presented; this protocol makes use of a safe acetaldehyde precursor to access important intermediates R/S-R1CH(CH2C(O)H)CH2NO2 to Active Pharmaceutical Ingredients (APIs), and allows the use of fewer equivalent of acetaldehyde and lower catalyst loadings. The reaction developed proved to be suitable to be performed on gram-scale and to produce key intermediates, such as (R)-5-methyl-3-(nitromethyl)hexanal for the synthesis of pharmacol. active compounds such as pregabalin.

Catalysts published new progress about Aldehydes Role: SPN (Synthetic Preparation), PREP (Preparation) (nitro). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Reference of 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Carmona, Maria; Rodriguez, Ricardo; Passarelli, Vincenzo; Carmona, Daniel published the artcile< Mechanism of the Alkylation of Indoles with Nitrostyrenes Catalyzed by Chiral-at-Metal Complexes>, Electric Literature of 5153-70-8, the main research area is alkylation indole nitrostyrene catalyzed chiral phosphinobenzyl pyridylmethyl amine rhodium; mol structure calculation phosphinobenzyl pyridylmethyl amine rhodium nitrostyrene complex.

Chiral-at-metal rhodium(III) complexes of the formula [Rh(κ4C,N,N’,P-L)A(Solv)][SbF6]n (Solv = A = MeCN, n = 2 (1); Solv = H2O, A = MeCN, n = 2 (2); Solv = MeCN, A = Cl, n = 1 (3); Solv = H2O, A = Cl, n = 1 (4)) catalyze the Friedel-Crafts reaction of trans-β-nitrostyrene and N-methyl-2-methylindole. Complex 4 reacts with trans-β-nitrostyrene, affording [RhCl(κ4C,N,N’,P-L)(trans-β-nitrostyrene)]+ (5). In the presence of N-methyl-2-methylindole, complex 5 reversibly gives a mixture of aci-nitro complexes 6 in high diastereoselectivity which, in turn, evolve to the FC adducts through 1,3-prototropy mediated by a water mol. On the basis of exptl. NMR studies and DFT calculations, a detailed mechanistic pathway for the alkylation reaction is proposed, including an explanation of the origin of the measured enantiomeric ratio.

Organometallics published new progress about Alkylation. 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Electric Literature of 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Aksenov, Alexander V.; Aksenov, Dmitrii A.; Arutiunov, Nikolai A.; Aksenov, Nicolai A.; Aleksandrova, Elena V.; Zhao, Zhenze; Du, Liqin; Kornienko, Alexander; Rubin, Michael published the artcile< Synthesis of Spiro[indole-3,5'-isoxazoles] with Anticancer Activity via a Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles>, Application In Synthesis of 5153-70-8, the main research area is spiroindoleisoxazole preparation anticancer formal spirocyclization nitroalkene indole.

An acid-assisted [4 + 1]-cycloaddition of indoles with nitrostyrenes affords 4’H-spiro[indole-3,5′-isoxazoles] in a diastereomerically pure form. Several of these spirocyclic mols. exhibit promising anticancer activity by reducing viability and inducing differentiation of neuroblastoma cells.

Journal of Organic Chemistry published new progress about Alkenes, nitro Role: RCT (Reactant), RACT (Reactant or Reagent). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Application In Synthesis of 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Ishitani, Haruro; Kanai, Kan; Yoo, Woo-Jin; Yoshida, Tomoko; Kobayashi, Shu published the artcile< A Nickel-Diamine/Mesoporous Silica Composite as a Heterogeneous Chiral Catalyst for Asymmetric 1,4-Addition Reactions>, SDS of cas: 5153-70-8, the main research area is nitroalkylmalonate enantioselective preparation; supported nickel diamine complex preparation recyclable catalyst enantioselective addition; enantioselective addition malonate nitroalkene supported nickel diamine catalyst; nitromethane enantioselective addition alkylidenemalonate supported nickel diamine catalyst; asymmetric 1,4-addition; asymmetric catalysis; flow synthesis; heterogeneous catalysis; mesoporous materials.

A nonracemic nickel diamine complex supported on the mesoporous silica MCM-41 was prepared from NiI2, (R,R)-BnNHCHPhCHPhNHBn, and MCM-41 was prepared as a recyclable catalyst for the enantioselective addition of di-Me malonate to nitroalkenes and for the enantioselective addition of nitromethane to alkylidenemalonates in the presence of morpholine. MCM-41 enhanced the reactivity and improved the stability of the included nickel diamine complex.

Angewandte Chemie, International Edition published new progress about 1,3-Dicarbonyl compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, SDS of cas: 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Rani, Dixita; Bhargava, Meha; Agarwal, Jyoti published the artcile< Asymmetric Michael Addition of Unactivated Ketones with β-Nitrostyrenes Mediated by Bifunctional L-Prolinamide Organocatalysts>, Quality Control of 5153-70-8, the main research area is nitrostyrene ketone orgnocatalyst diastereoselective Michael addition; nitrophenylethyl ketone preparation.

The catalytic activity of two types of L-prolinamide organocatalysts was investigated for asym. Michael addition reaction of cyclic/acyclic ketones with β-nitrostyrens. L-Prolinamides bearing amino groups as efficient catalyst as well as selectivity was found to be dependent upon the position of amine group to the amide bond. Organocatalyst having -NH2 group ortho to amide bond provided the best results. Substrate scope was also studied by performing the reaction of various β-nitrostyrenes with ketones to afforded the corresponding Michael adducts in excellent yields with very high diastereoselectivities and enantioselectivities in almost all cases.

ChemistrySelect published new progress about Alkenes, nitro Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, Quality Control of 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Akutsu, Hiroshi; Ito, Mifuyu; Kawada, Masahiro; Nakashima, Kosuke; Hirashima, Shin-ichi; Miura, Tsuyoshi published the artcile< Organocatalytic asymmetric conjugate addition of substituted 5-benzylfurfurals to nitroalkenes based on stereocontrol of trienamine>, HPLC of Formula: 5153-70-8, the main research area is nitroalkene benzylfurfural organocatalyst enantioselective diastereoselective regioselective alkylation; furan derivative preparation.

Asym. ε-alkylation reaction of substituted 5-benzylfurfural derivatives to nitroalkenes by controlling the stereochem. of the trienamine intermediate resulted in corresponding ε-regioselective addition products, e.g., I, in high yields, diastereoselectivities, and enantioselectivities.

Tetrahedron Letters published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 5153-70-8 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H6ClNO2, HPLC of Formula: 5153-70-8.

Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics