Day: November 10, 2022

Song, Bichao published the artcilePd-Catalyzed Decarboxylative Olefination: Stereoselective Synthesis of Polysubstituted Butadienes and Macrocyclic P-glycoprotein Inhibitors, Application of tert-Butyl piperidin-4-ylcarbamate, the main research area is vinylethylene carbonate diazo ester palladium decarboxylative olefination catalyst; vinyloxazolidinone diazo ester palladium decarboxylative olefination catalyst; vinylbenzoxazinone diazo ester palladium decarboxylative olefination catalyst; butadiene polysubstituted stereoselective preparation.

The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alc.-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.

Journal of the American Chemical Society published new progress about Allyl amines Role: SPN (Synthetic Preparation), PREP (Preparation). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Application of tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yamada, Kanako published the artcileCombined UV-irradiation and pyrolysis-GC/MS approach for evaluating the deterioration behavior of ethylene vinyl acetate, SDS of cas: 52829-07-9, the main research area is pyrolysis UV irradiation ethylene vinyl acetate.

Ethylene vinyl acetate (EVA), commonly used to encapsulate photovoltaic (PV) modules, deteriorates on prolonged exposure to sunlight. In this work, fresh and deteriorated EVA samples prepared by UV irradiation (500 W m-2) over different periods (0-168 h) are characterized by conventional elemental anal., microscopic observations, Fourier transform IR (FT-IR) spectroscopy, and thermogravimetry. To the best of our knowledge, this is the first work to employ pyrolysis-gas chromatog./mass spectrometry (Py-GC/MS) and micro-UV irradiation combined Py-GC/MS (UV/Py-GC/MS) to investigate the deterioration behavior of EVA, using in-situ identification of gases liberated during UV irradiation, such as H2O, CO2, ketones, acetic acid, and lactones. In addition, the deterioration of the thermal stability on aging is confirmed using evolved gas anal.-mass spectrometry (EGA-MS). UV/Py-GC/MS revealed that acetaldehyde, acetone, acetic acid, γ-butyrolactone, succinic anhydride, and cyclobutanone are produced during UV irradiation In addition, Py-GC/MS identified cyclopentanone, citraconic anhydride, γ-valerolactone, and cyclobutanone from the UV deteriorated EVA samples, which suggested the presence of ketone and lactone structures in the deteriorated EVA. This work establishes the combined usage of UV irradiation and Py-GC/MS as a promising method to investigate UV deterioration behavior in greater detail. These findings may contribute to a superior understanding of the breakdown of PV modules by the deterioration of EVA, and lead to the development of UV-resistant encapsulating materials.

Polymer Degradation and Stability published new progress about Anhydrides Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), PROC (Process). 52829-07-9 belongs to class piperidines, name is Bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate, and the molecular formula is C28H52N2O4, SDS of cas: 52829-07-9.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Hayhow, Thomas G. published the artcileA Buchwald-Hartwig Protocol to Enable Rapid Linker Exploration of Cereblon E3-Ligase PROTACs**, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is isoindolyl amine preparation; aryl bromide amine Buchwald Hartwig amination palladium catalyst; PEPPSI; PROTAC; amination; cereblon; drug discovery.

A palladium-catalyzed Buchwald-Hartwig amination for lenalidomide-derived aryl bromides was optimized using high throughput experimentation (HTE) to afford isoindolyl amines I [R1 = H, Me; R2 = n-Bu, Ph, 2-MeC6H4, etc.; R1R2 = (CH2)2O(CH2)2, (CH2)2CH(CH2OH)(CH2)2, (CH2)2N(Boc)(CH2)2, etc.]. The substrate scope of the optimized conditions was evaluated for a range of alkyl- and aryl- amines and functionalised aryl bromides. The methodol. allowed access to new cereblon-based bifunctional proteolysis targeting chimeras with a reduced step count and improved yields.

Chemistry – A European Journal published new progress about Aryl bromides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Yakukhnov, Sergey A. published the artcileCatalytic Transfer Hydrodebenzylation with Low Palladium Loading, Category: piperidines, the main research area is benzyl ester palladium catalyst hydrodebenzylation; ether benzyl palladium catalyst hydrodebenzylation; amine benzyl palladium catalyst hydrodebenzylation; aryl halide palladium catalyst hydrodehalogenation.

A highly-efficient catalytic system for hydrodebenzylation is described. The cleavage of O-benzyl and N-benzyl protecting groups was performed using an uncommonly low palladium loading (0.02-0.3 mol%; TON up to 5000) in a relatively short reaction time. This approach was used for a variety of substrates including pharmaceutically important precursors, and gram-scale deprotection was demonstrated. Transfer conditions and an easy-to-make Pd/C catalyst are key features of this debenzylation scheme.

Advanced Synthesis & Catalysis published new progress about Aromatic hydrocarbons Role: SPN (Synthetic Preparation), PREP (Preparation). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Category: piperidines.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Song, Jin Woo published the artcileSynthesis of Carbamoyl Fluorides via a Selective Fluorinative Beckmann Fragmentation, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate, the main research area is carbamoyl fluoride preparation; oximinoamide fluorinative Beckmann fragmentation.

A fluorinative Beckmann fragmentation of α-oximinoamides RC(O)C(CH3)=NOH [R = bis(cyclohexylmethyl)aminyl, piperidin-1-yl, morpholin-4-yl, etc.], I (n = 0, 1, 2) and II (R1 = Me, Ph, [5-(trifluoromethyl)furan-2-yl]methyl, etc.) was devised to provide synthetically useful carbamoyl fluorides RC(O)F, C6H5CH2N(CH2(CH2)nCH2CN)C(O)F and 2-CN-C6H4-N(R1)C(O)F. High selectivity for fragmentation over a potentially competing Beckmann rearrangement was observed This protocol has a distinct mechanism and it is a different substrate scope compared with other synthetic methods. The α-oximinoamides derived from the readily available secondary amines such as piperidine, morpholine, isoindoline, etc. lactams III, or isatins IV were converted into structurally diverse carbamoyl fluorides.

Organic Letters published new progress about Beckmann rearrangement. 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Recommanded Product: tert-Butyl piperidin-4-ylcarbamate.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Guo, Junkai published the artcileSulfoxFluor-enabled deoxyazidation of alcohols with NaN3, Synthetic Route of 887425-47-0, the main research area is alc sulfoxfluor sodiumazide deoxyazidation; alkyl azide preparation.

Direct deoxyazidation of alcs. with NaN3 is a straightforward method for the synthesis of widely used alkyl azides in organic chem. A general and practical method for the preparation of alkyl azides from alcs. using NaN3 was developed. N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor) played an important role in this deoxyazidation process, which converted a broad range of alcs. into alkyl azides at room temperature The power of this deoxyazidation protocol was demonstrated by successful late-stage deoxyazidation of natural products and pharmaceutically relevant mols.

Nature Communications published new progress about Alkyl azides Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 887425-47-0 belongs to class piperidines, name is 1-(5-Bromopyrimidin-2-yl)piperidin-4-ol, and the molecular formula is C9H12BrN3O, Synthetic Route of 887425-47-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Xie, Lan published the artcileLead Optimization: Synthesis and Biological Evaluation of PBT-1 Derivatives as Novel Antitumor Agents, Application In Synthesis of 73874-95-0, the main research area is phenanthrene tylophorine preparation antitumor activity SAR.

Phenanthrene-based tylophorine-1 (PBT-1) I (R = CH2OH, NHBoc, Me, SO2Me, etc.; R1 = H, OMe; R2 = OH, OMe, OAc, prop-2-yn-1-yloxidanyl, etc.; X = CH, N) and II (R3 = H, OMe; R4 = H, OMe) was identified previously as a lead compound in an anticancer drug discovery effort based on natural Tylophora alkaloids. An expanded structural optimization using a new more efficient synthetic route provided 14 PBT-derivatives I and II. Eleven compounds displayed obvious antiproliferative activities in cellular assays (GI50 0.55-9.32μM). The most potent compounds I (R = CH2OH, R1 = H, R2 = OH, X = CH; R = NHBoc, R1 = H, R2 = OH, X = CH; R = NH2, R1 = H, R2 = OH, X = CH) (GI50 ; 1μM) contained a 7-hydroxy group on the phenanthrene B-ring in addition to a pendant piperidine E-ring with different 4-substituents. While I (R = NH2, R1 = H, R2 = OH, X = CH) with NH2 as the piperidine substituent was at least 4-fold more potent against triple-neg. breast cancer MDA-MB-231 than estrogen-responsible breast cancer MCF-7 cell growth. In further biol. evaluations, the new active compounds induced cell cycle accumulation in late S and G2/M phase without interfering with microtubule formation or cell morphol. These results on the optimization of the B- and E-rings of PBT-1 I and II should benefit the further development of novel antitumor agents.

ACS Medicinal Chemistry Letters published new progress about Alkaloids Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 73874-95-0 belongs to class piperidines, name is tert-Butyl piperidin-4-ylcarbamate, and the molecular formula is C10H20N2O2, Application In Synthesis of 73874-95-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Chen, Xiaoqi published the artcileDiscovery and characterization of a potent and selective antagonist of melanin-concentrating hormone receptor 2, Computed Properties of 137419-24-0, the main research area is MCHR 2 antagonist carbazolylmethyl spiroindanpiperidine preparation.

A series of carbazoylylmethylindanspiropiperidines were synthesized and evaluated as MCHR2 antagonists using a FLIPR assay. The pharmacokinetic properties of selected compounds have also been studied. This effort led to the discovery of potent and specific MCHR2 antagonists. Thus, I demonstrated good pharmacokinetic properties across rat, beagle dog and rhesus monkey and had a favorable selectivity profile against a number of other receptors. These MCHR2 antagonists are considered appropriate tool compounds for study of the function of MCHR2 in vivo.

Bioorganic & Medicinal Chemistry Letters published new progress about. 137419-24-0 belongs to class piperidines, name is tert-Butyl spiro[indene-1,4′-piperidine]-1′-carboxylate, and the molecular formula is C18H23NO2, Computed Properties of 137419-24-0.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

DeVita, Robert J. published the artcileIdentification and initial structure-activity relationships of a novel non-peptide quinolone GnRH receptor antagonist, Synthetic Route of 27483-92-7, the main research area is quinolone gonadotropin releasing hormone receptor antagonist.

Screening of the Merck sample collection for non-peptide compounds with binding affinity for the rat GnRH (gonadotropin releasing hormone) receptor led to the identification of the substituted quinolone (I) as a lead compound in the search for a non-peptide GnRH receptor antagonist. Substantial improvements in potency (∼300 fold) were achieved by addition of an alkyl amine at the 4-position, a 3,5-dimethylphenyl group at the 3-position and 6-nitro-7-chloro-substitution of the 1H-quinolone core.

Bioorganic & Medicinal Chemistry Letters published new progress about Structure-activity relationship (gonadotropin releasing hormone receptor-antagonist). 27483-92-7 belongs to class piperidines, name is 2-(Chloromethyl)-1-methylpiperidine hydrochloride, and the molecular formula is C7H15Cl2N, Synthetic Route of 27483-92-7.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem

Logemann, Morten published the artcileContinuous gas-phase hydroformylation of but-1-ene in a membrane reactor by supported liquid-phase (SLP) catalysis, Product Details of C28H52N2O4, the main research area is butene hydroformylation membrane reactor liquid phase catalysis.

Process intensification is a cornerstone to achieve a significant reduction in energy consumption and CO2 emissions in the chem. industry. In this context, a monolithic membrane reactor combining homogeneous catalytic gas-phase hydroformylation of but-1-ene with in situ product removal is here presented. The homogeneous supported ionic liquid-phase (SILP) catalyst consists of a Rh-biphephos complex dissolved in 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide [C2C1Im][NTf2] and immobilized on a mesoporous silicon carbide monolith. The resulting monolith is catalytically active and selective towards linear aldehyde formation, but the accumulation of aldehyde products and high boilers in the ionic liquid leads to slow catalyst deactivation. This accumulation is suppressed when bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate is used as alternative solvent, where only marginal aldehyde accumulation and aldol formation occur. A polydimethylsiloxane (PDMS) membrane coating of the monolith increases the aldehyde-alkene ratio by an enrichment factor of 2.2 in the permeate gas compared to the retentate gas from the reactor simplifying further downstream processing. The monolithic membrane reactor loaded with SILP or SLP catalysts presents a scalable, versatile platform to achieve process intensification for diverse hydroformylation reactions as well as related gas-phase reactions.

Green Chemistry published new progress about Aldehydes, hydroxy Role: IMF (Industrial Manufacture), PREP (Preparation). 52829-07-9 belongs to class piperidines, name is Bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate, and the molecular formula is C28H52N2O4, Product Details of C28H52N2O4.

Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem