Day: October 12, 2022

Amani, Javad; Molander, Gary A. published the artcile< Direct Conversion of Carboxylic Acids to Alkyl Ketones>, Reference of 180181-05-9, the main research area is ketone preparation photoredox synergistic catalytic coupling carboxylic acid alkyltrifluoroborate; synergistic photoredox nickel catalytic coupling carboxylic acid alkyltrifluoroborate.

An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carboxylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.

Organic Letters published new progress about Carboxylic acids Role: RCT (Reactant), RACT (Reactant or Reagent) (activated). 180181-05-9 belongs to class piperidines, and the molecular formula is C22H23NO4, Reference of 180181-05-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Takahashi, Torizo; Kariyone, Kazuo published the artcile< Studies on insecticides. V. Synthesis of 2-piperidone derivatives>, Formula: C7H11NO3, the main research area is .

Distillation of 3-methyl-2(1H)-pyridone after hydrogenation gave two fractions: 3-methyl-2-piperidone, b8 128-31°, and 1,3-dimethylpiperidine (I); picrate m. 105°. NaNO2 (6.5 g.) in 30 ml. H2O added dropwise to 8.0 g. 2-amino-4-ethylpyridine in 120 ml. 10% HCl, the mixture stirred 0.5 hr., refluxed 3 hrs., and evaporated to dryness in vacuo, the residue dissolved in H2O, and the solution neutralized, extracted with CHCl3, dried, and concentrated in vacuo gave 5.5 g. 4-ethyl-2(1H)-pyridone (II). A solution containing 9.0 g. isonicotinic acid 1-oxide in 50 ml. MeOH and 1 g. H2SO4 refluxed 5 hrs., concentrated, diluted with 20 ml. H2O, neutralized, extracted with CHCl3, dried, and evaporated to dryness gave Me isonicotinate 1-oxide (III), m. 121° (acetone); picrate derivative m. 107° (EtOH). Hydrogenation of II and III yielded 4-ethyl-2-piperidone and Me 2-oxoisonipecotate, resp. Acetylation of 4-ethylpyridine 1-oxide gave 4-(1-hydroxyethyl)pyridine, m. 63°. III refluxed with Ac2O and concentrated in vacuo, the residue dissolved in H2O, and the solution neutralized and extracted with CHCl3 gave a 4-carbomethoxy-2(1H)-pyridone, m. 210° (acetone).

Chem. & Pharm. Bull. (Tokyo) published new progress about Insecticides. 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Formula: C7H11NO3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Deng, Yuqing; Peng, Jianzhao; Xiong, Feng; Song, Yinan; Zhou, Yu; Zhang, Jianfu; Lam, Fong Sang; Xie, Chao; Shen, Wenyin; Huang, Yiran; Meng, Ling; Li, Xiaoyu published the artcile< Selection of DNA-Encoded Dynamic Chemical Libraries for Direct Inhibitor Discovery>, Computed Properties of 180181-05-9, the main research area is DNA dynamics library inhibitor discovery; DNA; DNA-encoded dynamic libraries; drug discovery; dynamic combinatorial libraries; high-throughput screening.

Dynamic combinatorial libraries (DCLs) is a powerful tool for ligand discovery in biomedical research; however, the application of DCLs has been hampered by their low diversity. Recently, the concept of DNA encoding has been employed in DCLs to create DNA-encoded dynamic libraries (DEDLs); however, all current DEDLs are limited to fragment identification, and a challenging process of fragment linking is required after selection. The authors report an anchor-directed DEDL approach that can identify full ligand structures from large-scale DEDLs. This method is also able to convert unbiased libraries into focused ones targeting specific protein classes. The authors demonstrated this method by selecting DEDLs against five proteins, and novel inhibitors were identified for all targets. Notably, several selective BD1/BD2 inhibitors were identified from the selections against bromodomain 4 (BRD4), an important anti-cancer drug target. This work may provide a broadly applicable method for inhibitor discovery.

Angewandte Chemie, International Edition published new progress about Antitumor agents. 180181-05-9 belongs to class piperidines, and the molecular formula is C22H23NO4, Computed Properties of 180181-05-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Nakajima, Noriyuki; Saito, Miho; Ubukata, Makoto published the artcile< Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates>, Category: piperidines, the main research area is amide dehydration DMSO oxalyl chloride triethylamine nitrile preparation; imidate perfluoro preparation amide dehydration; methoxybenzyl perfluoro imidate alc protection.

Various types of primary amides were treated with an activated DMSO species, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoro imidates via volatile perfluoro nitriles from perfluoro amides. Fifteen benzyl-type perfluoro imidates were prepared in 70-90% yield as more stable imidates than the trichloro analog. MPM- and DMPM-perfluoro imidates can be used to protect alcs. in place of the trichloroacetimidate with excellent chem. properties and in comparable yields.

Tetrahedron published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Category: piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Badir, Shorouk O.; Lipp, Alexander; Krumb, Matthias; Cabrera-Afonso, Maria Jesus; Kammer, Lisa Marie; Wu, Victoria E.; Huang, Minxue; Csakai, Adam; Marcaurelle, Lisa A.; Molander, Gary A. published the artcile< Photoredox-mediated hydroalkylation and hydroarylation of functionalized olefins for DNA-encoded library synthesis>, Computed Properties of 180181-05-9, the main research area is phthalimide ester DNA conjugated trifluoromethyl alkene photoredox catalyst trifluoromethylation; DNA encoded trifluoromethylalkyl aryl amide preparation; alkene DNA conjugated aryl iodide photoredox catalyst reductive alkylation; alkylaryl DNA encoded amide preparation.

DNA-encoded library (DEL) technol. features a time- and cost-effective interrogation format for the discovery of therapeutic candidates in the pharmaceutical industry. To develop DEL platforms, the implementation of water-compatible transformations that facilitate the incorporation of multifunctional building blocks (BBs) with high C(sp3) carbon counts is integral for success. In this report, a decarboxylative-based hydroalkylation of DNA-conjugated trifluoromethyl-substituted alkenes enabled by single-electron transfer (SET) and subsequent hydrogen atom termination through electron donor-acceptor (EDA) complex activation was detailed. In a further photoredox-catalyzed hydroarylation protocol, the coupling of functionalized, electronically unbiased olefins was achieved under air and within minutes of blue light irradiation through the intermediacy of reactive (hetero)aryl radical species with full retention of the DNA tag integrity. Notably, these processes operate under mild reaction conditions, furnishing complex structural scaffolds with a high d. of pendant functional groups.

Chemical Science published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 180181-05-9 belongs to class piperidines, and the molecular formula is C22H23NO4, Computed Properties of 180181-05-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Nakajima, Noriyuki; Ubukata, Makoto published the artcile< Preparation of nitriles from primary amides under Swern oxidation conditions>, Related Products of 91419-53-3, the main research area is Swern oxidation carboxamide; nitrile preparation.

In order to establish a mild conversion method of primary amides to nitriles, various types of carboxamides were treated under Swern oxidation conditions, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain desired nitriles in 75-96% yields.

Tetrahedron Letters published new progress about Amides Role: RCT (Reactant), RACT (Reactant or Reagent). 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Related Products of 91419-53-3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Liu, Richard Y.; Bae, Minwoo; Buchwald, Stephen L. published the artcile< Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes>, Application of C11H18N2O2, the main research area is copper catalyst dehydration primary amide hydrosilane; nitrile preparation.

Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. A copper-hydride(CuH)-catalyzed process is reported that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups and can be performed using a simple ligand, inexpensive siloxanes and low catalyst loading.

Journal of the American Chemical Society published new progress about Amides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Application of C11H18N2O2.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Gross, Kathleen M. Bertini; Beak, Peter published the artcile< Complex-Induced Proximity Effects: The Effect of Varying Directing-Group Orientation on Carbamate-Directed Lithiation Reactions>, Recommanded Product: 1-Boc-2-Piperidineacetic acid, the main research area is proximity effect complex induced; carbamate directed lithiation.

A series of selected bicyclic carbamates in which the range of accessible angles and distances between the carbonyl group and the proton removed in an α-lithiation reaction are structurally defined have been investigated. Oxazolidinones I (n = 1, 2; R = i-Pr, t-Bu) undergo stereoselective lithiation-substitution reactions to provide cis-II as the major diastereomers. Two series of competition experiments show that the conformationally restricted carbamates undergo lithiation via complexes more efficiently than Boc amines (e.g., N-Boc-pyrrolidine, N-Boc-piperidine). These results along with semiempirical calculations suggest that a small dihedral angle and a calculated distance of 2.78 Å between the carbamate carbonyl oxygen and the proton to be removed are favorable for a carbamate-directed lithiation. A series of tin-lithium exchange experiments indicate that the configurational stability of a carbamate-stabilized organolithium species may be enhanced by restrictive geometry.

Journal of the American Chemical Society published new progress about Chelation (and configurational stability of carbanion intermediate). 149518-50-3 belongs to class piperidines, and the molecular formula is C12H21NO4, Recommanded Product: 1-Boc-2-Piperidineacetic acid.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yu, Tao; Tagat, Jayaram R.; Kerekes, Angela D.; Doll, Ronald J.; Zhang, Yonglian; Xiao, Yushi; Esposite, Sara; Belanger, David B.; Curran, Patrick J.; Mandal, Amit K.; Siddiqui, M. Arshad; Shih, Neng-Yang; Basso, Andrea D.; Liu, Ming; Gray, Kimberly; Tevar, Seema; Jones, Jennifer; Lee, Suining; Liang, Lianzhu; Ponery, Samad; Smith, Elizabeth B.; Hruza, Alan; Voigt, Johannes; Ramanathan, Lata; Prosise, Winifred; Hu, Mengwei published the artcile< Discovery of a Potent, Injectable Inhibitor of Aurora Kinases Based on the Imidazo-[1,2-a]-Pyrazine Core>, Category: piperidines, the main research area is imidazopyrazine pyrazolyl isothiazolylamino derivative preparation aurora kinase inhibition activity; pyrazolyl isothiazolylamino imidazopyrazine solubility antitumor activity; Aurora kinase inhibitors; SCH 1473759; aqueous solubility; cell potency; imidazo-[1,2-a]-pyrazine; tumor xenograft model.

The imidazo-[1,2-a]-pyrazine I is a dual inhibitor of Aurora kinases A and B with modest cell potency (IC50 = 250 nM) and low solubility (5 μM). Lead optimization guided by the binding mode led to the acyclic amino alc. II (SCH 1473759), which is a picomolar inhibitor of Aurora kinases (TdF Kd Aur A = 0.02 nM and Aur B = 0.03 nM) with improved cell potency (phos-HH3 inhibition IC50 = 25 nM) and intrinsic aqueous solubility (11.4 mM). It also demonstrated efficacy and target engagement in human tumor xenograft mouse models.

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 91419-53-3 belongs to class piperidines, and the molecular formula is C11H18N2O2, Category: piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Yilin; Du, Jianbo; Zuo, Zhiwei published the artcile< Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis>, Application of C7H11NO3, the main research area is hydrazine regioselective preparation photochem; ketone DIAD photochem carbon bond cleavage cerium catalyst.

A general catalytic manifold for selective C-C bond scission of ketones via exploitation of ligand-to-metal charge transfer (LMCT) excitation mode was reported. Through a cooperative utilization of Lewis acid catalysis and LMCT catalysis, the C-C bond of ketones could be selectively and effectively cleaved, enabling installation of different functionalities at each carbon of cleaved C-C bond through a sequential and orthogonal manner. This reaction manifold served as a photocatalytic alternative to Norrish type I reaction with combination of visible light and inexpensive cerium salts. Under operationally simple conditions, a wide range of acyclic and cyclic ketones, from simple strained cyclobutanones to complex androsterone with less strained cyclopentanone moiety, could be successfully transformed into versatile chem. building blocks.

Chem published new progress about Bond cleavage catalysts (C-C, regioselective). 25504-47-6 belongs to class piperidines, and the molecular formula is C7H11NO3, Application of C7H11NO3.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem