38112-59-3Relevant academic research and scientific papers
Active Base Hybrid Organosilica Materials based on Pyrrolidine Builder Units for Fine Chemicals Production
Llopis, Sebastián,Velty, Alexandra,Díaz, Urbano
, p. 5012 - 5024 (2021/10/19)
The catalytic activity of “pyrrolidine type” fragments included or anchored in the mesoporous silica supports or polymeric frameworks have been fully reported for enantioselective transformation. Nevertheless, low attention was focused on their catalytic abilities to perform base-catalyzed reaction. Accordingly, hybrid materials including pyrrolidine fragments in the mesoporous silica supports were prepared following different synthesis methods, such as micellar and fluoride sol-gel routes in absence of structural directing agents. Their great catalytic performance was explored for various base-catalyzed reactions to the formation of C?C bond through Knoevenagel, Claisen-Schmidt and Henry condensations under microwave irradiation. The benefits of microwave irradiation combined with suitable catalytic properties of pyrrolidine hybrid materials with strong base sites and high accessibility to active centers, allowed carrying out successfully base-catalyzed condensation reactions for the production of fine chemicals. Moreover, the hybrid catalyst exhibited high selectivity and good stability over different catalytic cycles contributing to environmental sustainability.
Synthesis of Rhamnolipid Derivatives Containing Ester Isosteres
Lowary, Todd L.,Wang, Lei
supporting information, p. 9633 - 9637 (2020/12/21)
Rhamnolipids are biosurfactants with many applications, arising from their inherent biological activity and their potential as bioremediation agents. Herein, we report the synthesis of four rhamnolipid derivatives in which the ester linkage connecting the
Solvent-free, one-pot synthesis of α,β-unsaturated esters in the presence of a C3-symmetric arsine
Wang, Changqing,Yang, Liu,Zhou, Rong,Mei, Guangquan
supporting information, p. 1074 - 1079 (2016/07/16)
An efficient synthesis of α, β-unsaturated esters is achieved via a one-pot reaction in the presence of a C3-symmetric arsine. The key advantages are the short reaction time, simple workup, mild reaction conditions, and high yields.
PDC-mediated tandem oxidative-wittig olefination
Dhumaskar, Kashinath L.,Bhat, Chinmay,Tilve, Santosh G.
supporting information, p. 1501 - 1506 (2014/05/20)
A convenient tandem oxidative-Wittig olefination of a primary alcohols to α,β-unsaturated compounds using pyridinium dichromate (PDC) is described.
Liquid chromatography/electrospray ionisation mass spectrometric tracking of 4-hydroxy-2(E)-nonenal biotransformations by mouse colon epithelial cells using [1,2-13C2]-4-hydroxy-2(E)-nonenal as stable isotope tracer
Jouanin,Baradat,Gieules,Tache,Pierre,Gueraud,Debrauwer
scheme or table, p. 2675 - 2681 (2012/03/10)
4-Hydroxy-2(E)-nonenal (HNE), a product of lipid peroxidation, has been extensively studied in several areas, including metabolism with radio-isotopes and quantification in various matrices with deuterium-labelled HNE as standard. The aim of this work was to evaluate the relevance of 13C-labelled HNE in biotransformation studies to discriminate metabolites from endogens by liquid chromatography/electrospray ionisation mass spectrometry (LC/ESI-MS). 13C-Labelled HNE was synthesised inimproved overall yield (20%), with the incorporation of two labels in the molecule. Immortalisedmouse colon epithelial cells were incubated with 2:3 molar amounts of HNE/13C-HNE in order to gain information on the detection of metabolites in complex media. Our results demonstrated that the stable isotope m/z values determined by mass spectrometry were relevant in distinguishing metabolites from endogens, and that metabolite structures could be deduced. Six conjugate metabolites and 4-hydroxy-2(E)-nonenoic acid were identified, together with an incompletely identified metabolite. Stable-isotope-labelled HNE has already been used for quantification purposes. However, this is the first report on the use of 13C-labelled HNE as a tracer for in vitro metabolism. 13C-Labelled HNE could also be of benefit for in vivo studies. Copyright
Titanocene-promoted eliminations on epoxy alcohols and epoxy esters
Fernandez-Mateos, Alfonso,Madrazo, Soledad Encinas,Teijon, Pablo Herrero,Gonzalez, Rosa Rubio
supporting information; experimental part, p. 856 - 861 (2010/04/05)
The reaction of a series of 2,3-epoxy alcohols and the corresponding formates, acetates, and benzoates promoted by Cp2TiCl has been studied. The different outcome of the reaction of epoxy derivatives has been rationalized in terms of mechanistically biased processes. After homolytic oxirane cleavage, four main types of reaction were found: dehydroxylation, decarboxylation, dehydrogenation, and deoxygenation. The reaction products varied according to the substitution pattern. The radical nature of these eliminations is demonstrated.
P[N(i-Bu)CH2CH2]3N: Nonionic Lewis base for promoting the room-temperature synthesis of α,β-unsaturated esters, fluorides, ketones, and nitriles using Wadsworth - Emmons phosphonates
Chintareddy, Venkat Reddy,Ellern, Arkady,Verkade, John G.
supporting information; experimental part, p. 7166 - 7174 (2010/12/25)
The bicyclic triaminophosphine P(RNCH2CH2) 3N (R = i-Bu, 1c) serves as an effective promoter for the room-temperature stereoselective synthesis of α,β-unsaturated esters, fluorides, and nitriles from a wide array of aromatic, aliphatic, heterocyclic, and cyclic aldehydes and ketones, using a range of Wadsworth-Emmons (WE) phosphonates. Among the analogues of 1c [R = Me (1a), i-Pr (1b), Bn (1d)], 1a and 1b performed well, although longer reaction times were involved, and 1d led to poorer yields than 1c. Functionalities such as cyano, chloro, bromo, methoxy, amino, ester, and nitro were well tolerated. We were able to isolate and characterize (by X-ray means; see above) the reactive WE intermediate species formed from 2b and 1c.
Catalytic synthesis of (E)-a,β-unsaturated esters from aldehydes and 1,1-diethoxyethylene
Manzano, Ruben,Ozores, Lidia,List, Benjamin,Job, Andreas,Rodefeld, Lars
experimental part, (2010/04/22)
A practical and high yielding synthesis of a,β-unsaturated esters from aldehydes and 1,1-diethoxyethylene was developed.
Synthesis of the lipid peroxidation product 4-hydroxy-2(E)-nonenal with 13C stable isotope incorporation
Jouanin,Sreevani,Rathahao,Gueraud,Paris
, p. 87 - 92 (2008/09/19)
The aim of this work was to synthesize 13C internal standards for the quantification of 4-hydroxy-2(E)-nonenal (HNE), a lipid peroxidation product, and of the etheno-adducts possibly formed by HNE damage to DNA nucleobases. We designed an eight-step synthesis starting from ethyl 2-bromoacetate and giving access to 4-[(tetrahydro-2H-pyran-2-yl)oxy]-2(E)- nonenal. This compound is a precursor of HNE. The scheme was then used to produce the 13C precursor [1,2-13C2]-4- [(tetrahydro-2H-pyran-2-yl)oxy]-2(E)-nonenal. [1,2-13C 2]HNE was obtained by acid deprotection. All the intermediary and final compounds were fully characterized by IR, HRMS, 1H and 13C NMR. It is the first synthesis of HNE which enables the incorporation of two 13C labels at determined positions. Copyright
A highly stereoselective TMSOTf-mediated catalytic carbocupration of alkynoates
Mueller, Amanda J.,Jennings, Michael P.
, p. 5327 - 5329 (2008/09/17)
(Chemical Equation Presented) The TMSOTf-mediated catalytic carbocupration of ynoates has been investigated. It has been shown that catalyst loadings as low as 5 mol % readily allow for high yields and diastereosetectivities for a series of aromatic Grignard reagents. In addition, we have been successful in vicinally functionalizing 1a via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.
