74213-58-4

Upstream product

• 163010-72-8 N-benzoyl-(S)-phenylglycinal 
• 56613-80-0 D-2-phenylglycinol 
• 98-88-4 benzoyl chloride 
• 2935-35-5 (S)-2-phenylglycine 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 81912-50-7 (S)-benzoylamino-phenyl-acetic acid methyl ester 
• 875-74-1 (R)-phenylglycine 
• 100-44-7 benzyl chloride 
• 1575722-54-1 (R)-N-(2-((4-methoxybenzyl)oxy)-1-phenylethyl)benzamide 
• 65-85-0 benzoic acid 
• 20989-17-7 Phenylglycinol 
• 60-12-8 2-phenylethanol 
• 26630-25-1 N-phenoxybenzimidic acid chloride 
• 2085-31-6 2-diazo-1,3-diphenylpropane-1,3-dione 

Downstream Products

• 155242-42-5 2,4-diphenyl-Δ²-oxazoline 
• 180999-33-1 N-(1-phenyl-2-phenylsulfanyl-ethyl)-benzamide 
• 132273-98-4 (2S,4R)-N-benzyl-2-methyl-4-phenyl-1,3-oxazolidine 
• 132273-88-2 (2R,4R)-N-benzyl-2-methyl-4-phenyl-1,3-oxazolidine 
• 140170-63-4 (2R,4R)-3-benzyl-2-ethyl-4-phenyloxazolidine 
• 141548-84-7 (2R,4R)-3-benzyl-4-phenyl-3-propyloxazolidine 
• 171561-72-1 (2R,4R)-N,2-dibenzyl-4-phenyl-1,3-oxazolidine 
• 177362-28-6 (R)-3-benzyl-4-phenyloxazolidine 
• 1153474-59-9 (E)-1-ethoxycarbonyl-2,2,2-trifluoroethylidene (1R)-2-benzoyloxy-1-phenylethylamine 
• 1575722-54-1 (R)-N-(2-((4-methoxybenzyl)oxy)-1-phenylethyl)benzamide 

Relevant academic research and scientific papers

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

Insights into the antiproliferative mechanism of (C^N)-chelated half-sandwich iridium complexes

Transition metal-based anticancer compounds, as an alternative to platinum derivatives, are raising scientific interest as they may present distinct although poorly understood mechanisms of action. We used a structure-activity relationship-based methodology to investigate the chemical and biological features of a series of ten (C^N)-chelated half-sandwich iridiumIII complexes of the general formula [IrCp?(phox)Cl], where (phox) is a 2-phenyloxazoline ligand forming a 5-membered metallacycle. This series of compounds undergoes a fast exchange of their chlorido ligand once solubilised in DMSO. They were cytotoxic to HeLa cells with IC50 values in the micromolar range and induced a rapid activation of caspase-3, an apoptosis marker. In vitro, the oxidative power of all the complexes towards NADH was highlighted but only the complexes bearing substituents on the oxazoline ring were able to produce H2O2 at the micromolar range. However, we demonstrated using a powerful HyPer protein redox sensor-based flow cytometry assay that most complexes rapidly raised intracellular levels of H2O2. Hence, this study shows that oxidative stress can partly explain the cytotoxicity of these complexes on the HeLa cell line and gives a first entry to their mechanism of action. This journal is

Enantioselective radical C–H amination for the synthesis of β-amino alcohols

Asymmetric, radical C–H functionalizations are rare but powerful tools for solving modern synthetic challenges. Specifically, the enantio- and regioselective C–H amination of alcohols to access medicinally valuable chiral β-amino alcohols remains elusive. To solve this challenge, a radical relay chaperone strategy was designed, wherein an alcohol was transiently converted to an imidate radical that underwent intramolecular H-atom transfer (HAT). This regioselective HAT was also rendered enantioselective by harnessing energy transfer catalysis to mediate selective radical generation and interception by a chiral copper catalyst. The successful development of this multi-catalytic, asymmetric, radical C–H amination enabled broad access to chiral β-amino alcohols from a variety of alcohols containing alkyl, allyl, benzyl and propargyl C–H bonds. Mechanistic experiments revealed that triplet energy sensitization of a Cu-bound radical precursor facilitates catalyst-mediated HAT stereoselectivity, enabling the synthesis of several important classes of chiral β-amines by enantioselective, radical C–H amination. [Figure not available: see fulltext.]

Method for preparing amide compound from 2-diazo-1, 3-dicarbonyl compound as acylating agent

The invention provides a method for preparing an amide compound from a 2-diazo-1, 3-dicarbonyl compound as an acylating agent under non-metallic catalysis and neutral conditions. The method uses 2-diazo-1, 3-dicarbonyl compound as a raw material and carries out different benzoyl protection on different amino compounds so that a series of amide compounds are prepared. The method is carried out under neutral conditions, prevents the limitation of reaction substrates under conventional alkaline conditions, and has mild reaction conditions, high reaction efficiency and a simple operation method. The method provides a new and convenient method for preparation of amide compounds and protection of amino groups and can be used in the fields of chemical medicine, biology and materials.

Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers

Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance.

Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles

Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated

Cycloadditions of aromatic azomethine imines with 1,1-cyclopropane Diesters

The cycloaddition of aromatic azomethine imines to 1,1-cyclopropane diesters was achieved using Ni(CIO4)2 as catalyst. The methodology gives access to unique tricyclic dihydroquinoline derivatives with dr up to 6.6:1. A nonconcerted

Combining Magnetic Resonance Spectroscopies, Mass Spectrometry, and Molecular Dynamics: Investigation of Chiral Recognition by 2,6-di-O-Methyl-β-cyclodextrin

EPR spectroscopy has been employed to investigate the formation of complexes between heptakis-(2,6-O-dimethyl)-β-cyclodextrin (DM-β-CD) and different enantiomeric pairs of chiral nitroxides of general structure PhCH2N(O·)CH(R)R′. Accurate equilibrium measurements of the concentrations of free and included radicals afforded the binding constant values for these nitroxides. The relationship between the stereochemistry of the DM-β-CD complexes and the thermodynamics of complexation was elucidated by correlating EPR data with 1H-1H NOE measurements carried out on the complexes between DM-β-CD and the structurally related amine precursors of nitroxides. NOE data suggested that inclusion of the stereogenic center in the DM-β-CD cavity occurs only when the R substituent linked to the chiral carbon contains an aromatic ring. For these types of complexes, molecular dynamics simulation indicated that the depth of penetration of the stereogenic center into the cyclodextrin cavity is determined by the nature of the second substituent (R′) at the asymmetric carbon and is responsible for the observed chiral selectivity. Analysis of mass spectra showed that, for the presently investigated amines, electrostatic external adducts of CDs with protonated amines are detected by ESI-MS.

Highly potent inhibitors of TNF-α production. Part I: Discovery of new chemical leads and their structure-activity relationships

Discovery of new chemical leads of inhibitors for TNF-α production starting from the chemical modification of 1 is reported. Further biological studies of 1 to disclose the site of its action strongly suggested that 1 inhibits LPS-induced TNF-α expression

Chiral β-amino sulfoxides. Synthesis, configurational assignment and conformational analysis based on X-ray, CD, 1H NMR and theoretical calculations

Enantiomerically pure u and l β-amino sulfoxides have been easily obtained from the respective homochiral α-amino alcohols. The absolute configuration at the created stereogenic centre was assigned by CD spectra and by X-ray analysis. Conformational analysis of the title compounds was carried out using quantum chemical energy-geometry optimization. Thus established conformational behavior explained the strongly configuration dependent NMR spectral patterns observed for the u and l diastereomers.