Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Ambiphilicity of ring-expanded N-heterocyclic carbenes† † Electronic supplementary information (ESI) available. CCDC 2291449, 2291450–2291455. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc04543a

ABSTRACT:

SUBMITTER: Vermersch F

PROVIDER: S-EPMC10915854 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

1-Azahomocubane† † Electronic supplementary information (ESI) available. CCDC 2177501. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc00001j

Project description:Highly strained cage hydrocarbons have long stood as fundamental molecules to explore the limits of chemical stability and reactivity, probe physical properties, and more recently as bioactive molecules and in materials discovery. Interestingly, the nitrogenous congeners have attracted much less attention. Previously absent from the literature, azahomocubanes, offer an opportunity to investigate the effects of a nitrogen atom when incorporated into a highly constrained polycyclic environment. Herein disclosed is the synthesis of 1-azahomocubane, accompanied by comprehensive structural characterization, physical property analysis and chemical reactivity. These data support the conclusion that nitrogen is remarkably well tolerated in a highly strained environment. 1-Azahomocubane has been prepared 56 years after the parent hydrocarbon. Introduction of a nitrogen atom into this constrained polycyclic environment resulted in minimal changes to the framework geometry, with s-character of the nitrogen lone pair increasing due to strain.

| S-EPMC10016339 | biostudies-literature

Terminal dysprosium and holmium organoimides† † Electronic supplementary information (ESI) available. CCDC 2312212–2312226. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc06584g

Project description: Not available

| S-EPMC10915843 | biostudies-literature

Synthesis and reactivity of N-heterocyclic carbene (NHC)-supported heavier nitrile ylides† † Electronic supplementary information (ESI) available. CCDC 2300364–2300367. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc06430a

Project description: Not available

| S-EPMC10866356 | biostudies-literature

Catalytic generation of ortho-quinone dimethides via donor/donor rhodium carbenes† † Electronic supplementary information (ESI) available. CCDC 2087127–2087130, 2087132–2087135, 2087415, 2145030, 2240749. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc00734k

Project description:Substrates engineered to undergo a 1,4-C–H insertion to yield benzocyclobutenes resulted in a novel elimination reaction to yield ortho-quinone dimethide (o-QDM) intermediates that undergo Diels–Alder or hetero-Diels–Alder cycloadditions. The analogous benzylic acetals or ethers avoid the C–H insertion pathway completely and, after hydride transfer, undergo a de-aromatizing elimination reaction to o-QDM at ambient temperature. The resulting dienes undergo a variety of cycloaddition reactions with high diastereo- and regio-selectivity. This is one of the few examples of catalytic generation of o-QDM without the intermediacy of a benzocyclobutene and represents one of the mildest, ambient temperature processes to access these useful intermediates. This proposed mechanism is supported by DFT calculations. Moreover, the methodology was applied to the synthesis of (±)-isolariciresinol in 41% overall yield. Substrates engineered to undergo a 1,4-C–H insertion to yield benzocyclobutenes resulted in a novel elimination reaction to yield ortho-quinone dimethide (o-QDM) products that undergo Diels–Alder or hetero-Diels–Alder cycloadditions.

| S-EPMC10266466 | biostudies-literature

Enantioselective nickel-catalyzed Mizoroki–Heck cyclizations of amide electrophiles† † Electronic supplementary information (ESI) available. CCDC 2271421. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc05797f

Project description: Not available

| S-EPMC10866352 | biostudies-literature

On pyridine chloronium cations† † Electronic supplementary information (ESI) available. CCDC 2223424, 2223431, 2223423, 2223425, 2223439 and 2223421. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2sc06757a

Project description:We present the first solid-state structural evidence of mono- and bis(pyridine)chloronium cations. The latter was synthesized from a mixture of pyridine, elemental chlorine and sodium tetrafluoroborate in propionitrile at low temperatures. The mono(pyridine) chloronium cation was realized with the less reactive pentafluoropyridine, using ClF, AsF5, and C5F5N in anhydrous HF. During the course of this study, we also investigated pyridine dichlorine adducts and found a surprising disproportionation reaction of chlorine that depended on the substitutional pattern of the pyridine. Electron richer dimethylpyridine (lutidine) derivatives favor full disproportionation into a positively and a negatively charged chlorine atom which forms a trichloride monoanion, while unsubstituted pyridine forms a 1 : 1 py·Cl2 adduct. The lutidine elephants are pulling apart a dichlorine molecule and stabilizing the corresponding chloronium cation. The remaining chloride forms a trichloride anion. Unsubstituted pyridine, however, only forms a strongly polarized dichlorine adduct.

| S-EPMC9977394 | biostudies-literature

Computation meets experiment: identification of highly efficient fibrillating peptides† † Electronic supplementary information (ESI) available: CCDC 2174444–2174447. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3ce00495c

Project description:Self-assembling peptides are of huge interest for biological, medical and nanotechnological applications. The enormous chemical variety that is available from the 20 amino acids offers potentially unlimited peptide sequences, but it is currently an issue to predict their supramolecular behavior in a reliable and cheap way. Herein we report a computational method to screen and forecast the aqueous self-assembly propensity of amyloidogenic pentapeptides. This method was found also as an interesting tool to predict peptide crystallinity, which may be of interest for the development of peptide based drugs. 8000 pentapeptides were computed though CG-MD starting from the model sequence DFNKF. Based on experimental validation, theoretical conditions (solubility and aggregation propensity) which may favor crystallization or fibrillation were identified.

| S-EPMC10424810 | biostudies-literature

A metal-free strategy to construct fluoroalkyl–olefin linkages using fluoroalkanes† † Electronic supplementary information (ESI) available. CCDC 2299679. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc05616c

Project description: Not available

| S-EPMC10829021 | biostudies-literature

Investigating the diastereoselective synthesis of a macrocycle under Curtin–Hammett control† † Electronic supplementary information (ESI) available. CCDC 2249179. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d3sc05715a

Project description: Not available

| S-EPMC11023033 | biostudies-literature

Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins† † Electronic supplementary information (ESI) available. CCDC 2207448. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2sc06497a

Project description:Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks. However, these reactions often require transition-metal catalysis, and are mainly limited to 1,2-carboamination. Herein, we report a novel radical relay 1,4-carboimination across two distinct olefins with alkyl carboxylic acid-derived bifunctional oxime esters via energy transfer catalysis. The reaction is highly chemo- and regioselective, and multiple C–C and C–N bonds were formed in a single orchestrated operation. This mild and metal-free method features a remarkably broad substrate scope with excellent tolerance of sensitive functional groups, therefore providing easy access to structurally diverse 1,4-carboiminated products. Moreover, the obtained imines could be easily converted into valuable biologically relevant free γ-amino acids. Intermolecular carboamination of olefins offers a powerful platform for the rapid construction of structurally complex amines from abundant feedstocks.

| S-EPMC9977457 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data