81580-50-9Relevant academic research and scientific papers
A novel synthesis of polysubstituted naphthalenes
Kiselyov
, p. 5321 - 5326 (2001)
The reaction of (2-trifluoromethyl)phenyl acetic acid derivatives with anions derived from aromatic acetonitriles furnishes polysubstituted naphthalenes in good yields (30-68%). A solid-phase version of this reaction is reported as well. The transformation is proposed to proceed via the intermediate formation of the quinone methide intermediate.
Thermal Stability and Explosive Hazard Assessment of Diazo Compounds and Diazo Transfer Reagents
Green, Sebastian P.,Wheelhouse, Katherine M.,Payne, Andrew D.,Hallett, Jason P.,Miller, Philip W.,Bull, James A.
supporting information, p. 67 - 84 (2020/01/31)
Despite their wide use in academia as metal-carbene precursors, diazo compounds are often avoided in industry owing to concerns over their instability, exothermic decomposition, and potential explosive behavior. The stability of sulfonyl azides and other diazo transfer reagents is relatively well understood, but there is little reliable data available for diazo compounds. This work first collates available sensitivity and thermal analysis data for diazo transfer reagents and diazo compounds to act as an accessible reference resource. Thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and accelerating rate calorimetry (ARC) data for the model donor/acceptor diazo compound ethyl (phenyl)diazoacetate are presented. We also present a rigorous DSC dataset with 43 other diazo compounds, enabling direct comparison to other energetic materials to provide a clear reference work to the academic and industrial chemistry communities. Interestingly, there is a wide range of onset temperatures (Tonset) for this series of compounds, which varied between 75 and 160 °C. The thermal stability variation depends on the electronic effect of substituents and the amount of charge delocalization. A statistical model is demonstrated to predict the thermal stability of differently substituted phenyl diazoacetates. A maximum recommended process temperature (TD24) to avoid decomposition is estimated for selected diazo compounds. The average enthalpy of decomposition (?"HD) for diazo compounds without other energetic functional groups is-102 kJ mol-1. Several diazo transfer reagents are analyzed using the same DSC protocol and found to have higher thermal stability, which is in general agreement with the reported values. For sulfonyl azide reagents, an average ?"HD of-201 kJ mol-1 is observed. High-quality thermal data from ARC experiments shows the initiation of decomposition for ethyl (phenyl)diazoacetate to be 60 °C, compared to that of 100 °C for the common diazo transfer reagent p-acetamidobenzenesulfonyl azide (p-ABSA). The Yoshida correlation is applied to DSC data for each diazo compound to provide an indication of both their impact sensitivity (IS) and explosivity. As a neat substance, none of the diazo compounds tested are predicted to be explosive, but many (particularly donor/acceptor diazo compounds) are predicted to be impact-sensitive. It is therefore recommended that manipulation, agitation, and other processing of neat diazo compounds are conducted with due care to avoid impacts, particularly in large quantities. The full dataset is presented to inform chemists of the nature and magnitude of hazards when using diazo compounds and diazo transfer reagents. Given the demonstrated potential for rapid heat generation and gas evolution, adequate temperature control and cautious addition of reagents that begin a reaction are strongly recommended when conducting reactions with diazo compounds.
Chemoenzymatic synthesis and antileukemic activity of novel C9- and C14-functionalized parthenolide analogs
Tyagi, Vikas,Alwaseem, Hanan,O'Dwyer, Kristen M.,Ponder, Jessica,Li, Qi Ying,Jordan, Craig T.,Fasan, Rudi
, p. 3876 - 3886 (2016/08/04)
Parthenolide is a naturally occurring terpene with promising anticancer properties, particularly in the context of acute myeloid leukemia (AML). Optimization of this natural product has been challenged by limited opportunities for the late-stage functionalization of this molecule without affecting the pharmacologically important α-methylene-γ-lactone moiety. Here, we report the further development and application of a chemoenzymatic strategy to afford a series of new analogs of parthenolide functionalized at the aliphatic positions C9 and C14. Several of these compounds were determined to be able to kill leukemia cells and patient-derived primary AML specimens with improved activity compared to parthenolide, exhibiting LC50values in the low micromolar range. These studies demonstrate that different O–H functionalization chemistries can be applied to elaborate the parthenolide scaffold and that modifications at the C9 or C14 position can effectively enhance the antileukemic properties of this natural product. The C9-functionalized analogs 22a and 25b were identified as the most interesting compounds in terms of antileukemic potency and selectivity toward AML versus healthy blood cells.
Role of ortho -substituents on rhodium-catalyzed asymmetric synthesis of β-lactones by intramolecular C-H insertions of aryldiazoacetates
Fu, Liangbing,Wang, Hengbin,Davies, Huw M.L.
supporting information, p. 3036 - 3039 (2014/06/23)
A rhodium-catalyzed asymmetric synthesis of β-lactones via intramolecular C-H insertion into the ester group of aryldiazoacetates has been developed. The β-lactones were synthesized in high yields and with high levels of diastereo- and enantioselectivity.
MULTIPLE KINASE PATHWAY INHIBITORS
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Page/Page column 267-269; 281, (2014/04/17)
Kinase with inhibitory activity against kinases disposed in multiple signaling pathways and their therapeutic uses.
Electrochemistry of Ethyl α-Bromo-α-fluoro(phenyl)acetate and some Ethyl α-Bromo(trifluoromethylphenyl)acetates and Electrochemical Synthesis of the Corresponding Diastereoisomeric Diethyl Succinates.
Mattiello, Leonardo,Rampazzo, Liliana,Sotgiu, Giovanni
, p. 2732 - 2754 (2007/10/02)
Ethyl α-bromoesters (1)-(5) (ABr) were prepared through NBS bromination of (6)-(10) (AH) respectively.Controlled potential electrolysis of (1)-(5), dissolved in dry dimethylformamide (DMF) containing Et4NClO4 (0.1 M) allows the corresponding succinates (1
