111-81-9Relevant articles and documents
Comparison of reactivity in the cross metathesis of allyl acetate-derivatives with oleochemical compounds
Behr, Arno,Toepell, Stephanie
, p. 603 - 611 (2015)
The metathesis of unsaturated oleochemicals is an excellent tool for generating α,ω-difunctional substrates, which are useful intermediates for polymer synthesis. This article describes the cross metathesis of allyl acetate and cis-1,4-diacetoxy-2-butene with methyl 10-undecenoate and methyl oleate, which are oleochemical key substrates. Detailed optimizations led to high conversion rates and yields of the desired products under mild reaction conditions by using a low concentration of commercially available homogeneous ruthenium catalysts.
Synthesis and biological evaluation of 3,6-dialkylsubstituted-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles
Venepally, Vijayendar,Sirisha,Kumar, C Ganesh,Krishna, E Vamshi,Misra, Sunil,Jala, Ram Chandra Reddy
, (2018)
Abstract: A series of 3,6-dialkyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole (10) analogues were prepared through multistep synthesis and evaluated them for their antimicrobial and cytotoxic activities. Synthesis of target compounds was carried out using undecenoic acid as starting material, which is the renewable product of castor oil. The key step in the synthesis was formation of triazolo [3,4-b][1,3,4]thiadiazole using various free fatty acids in presence of POCl 3. It was observed that the undecenyl based triazolothiadiazole with butyl (6a), hexyl (6b) and lauryl (6f) derivatives exhibited promising antimicrobial activity against the tested strains. Particularly, Compound 6a exhibited the most promising activity with MIC value 3.9 μ g / mL against most of the tested strains. It also showed potent minimum bactericidal concentration activity with MIC value 7.8 μ g / mL against the tested strains. Cytotoxicity data revealed that most of the tested compounds revealed cytotoxic activity, Compounds 6b, 6d, 6f, 6g, 6h and 6i against SKOV3, 6d, 6e, 6f, 6g, 6h, 6i and 6j against MCF-7 and 6c, 6d, 6e,6g, 6h, 6i and6j against B16–F10 cell lines exhibited significant activities with IC 50 values ranged between 13.67 and 18.62 μ M. Interestingly, all the compounds were non toxic against Chinese hamster ovary cell (CHO-K1) normal cell. Graphical Abstract : A series of 3, 6-dialkyl triazolothiadiazole analogues were prepared using undecenoic acid, which is the renewable product of castor oil and evaluated them for their antimicrobial and cytotoxic activities. Few compounds showed good antimicrobial and cytotoxic activities. [Figure not available: see fulltext.].
Anchoring molecular magnets on the Si(100) surface
Condorelli, Guglielmo G.,Motta, Alessandro,Fragala, Ignazio L.,Giannazzo, Filippo,Raineri, Vito,Caneschi, Andrea,Gatteschi, Dante
, p. 4081 - 4084 (2004)
Hydrosilylation by H-terminated silicon of the double bond of methyl 10-undecenoate with formation of a robust Si-C bond is the first step in a three-step procedure (see scheme) for anchoring the single-molecule magnet (SMM) [Mn12O12(OAc)16(H2O)4] (1) on the Si(100) surface.
Designing, synthesis, and antimicrobial action of oxazoline and thiazoline derivatives of fatty acid esters
Ahmad, Anis,Ahmad, Aiman,Sudhakar, Raja,Varshney, Himani,Subbarao, Naidu,Ansari, Saba,Rauf, Abdul,Khan, Asad U.
, p. 3412 - 3431 (2017)
In this study, a novel series of oxazoline and thiazoline were designed as inhibitors of cytochrome P450 14 alpha-sterol demethylase (CYP51) from Candida albicans and peptide deformylase (PDF) of Escherichia coli. The long chain dibromo derivative of fatty acid esters on reaction with urea and thiourea gave their corresponding oxazolines and thiazolines, respectively. All the compounds were characterized by their spectral data (IR, 1H NMR, 13C NMR and MS) and tested for antibacterial and antifungal activity by disk diffusion assay and minimum inhibitory concentration by the broth microdilution method against gram-positive and gram-negative strains of bacteria as well as fungus strains. The investigation into antimicrobial screening revealed that all the compounds were found to be potent antimicrobial agents. After calculating likeness drug properties of the compounds by Prediction of Activity Spectra for Substances software, ADMET-related descriptors were computed to predict the pharmacokinetic properties for the active and bioavailable compounds by discovery studio 2.5. Molecular docking studies have been performed on PDF of E. coli and CYP 450-14DM of C. albicans to understand the mode of binding of the molecules in the active site of the receptor. Compounds (2-amino-5-(carbomethoxyoctyl)-1,3-oxazoline, 2-amino-5-(carbomethoxyoctyl)-1,3-thiazoline and 2-amino-4-pentyl-5-[(8’R)-8’ hydroxy (carbomethoxydecyl)-1,3-oxazoline) showed excellent antimicrobial activity nearly equivalent to the control compounds and compounds, 2-amino-4-octyl-5-(carbomethoxyheptyl)-1,3-oxazolin, 2-amino-4-(2’R)(2’-hydroxy octyl)-5-(carbomethoxyheptyl)-1,3-oxazoline and 2-amino-4-pentyl-5-[(8’R)-8’-hydroxy(carbomethoxy decyl)-1,3-oxazolineshowed vasodilation and antihypertensive properties. Furthermore, a computational analysis of physicochemical parameters revealed that the most of the compounds possessed drug-like attributes. Using Bioinformatics approach, we found a correlation between the observed and predicted antimicrobial activities.
Factors influencing orientations of covalently-attached and doped aromatic groups in stretched polyethylene films
Wang, Caihua,Xu, Jinqi,Weiss, Richard G.
, p. 7015 - 7025 (2003)
Linear polarizations have been measured for covalently attached and doped 9-anthryl and 1-pyrenyl groups residing in interior sites of stretched polyolefinic films. The influences of polymer crystallinity, the concentration of aromatic groups and the length of the substituents attached to doped molecules or of the tethers to polymer chains of covalently attached species on the degree of polarization have been explored. The results demonstrate the utility of comparing orientational parameters from doped and covalently attached groups in analyzing the factors responsible for stretch-induced orientation. The anthryl and pyrenyl groups prefer to reside in interfacial regions more than amorphous regions even before film stretching, and the specificity of their orientations is determined by the nature of interactions with surrounding polymer chains. The magnitudes of orientation factors are dependent on polymer crystallinity and substituent or tether length, but are independent of aromatic group concentrations as long as they are low. There are significant differences between the orientations of doped and covalently attached groups of the same type due to the inability of the latter to translocate between site types during film stretching. The results, as interpreted in the context of current theories, demonstrate the necessity of crystallite surfaces (i.e., interfacial sites), but not stretching-induced translocation, for selective orientation of aromatic groups along the axis of stretching.
ANTIINFLAMMATORY AND ANALGESIC ACTIVITY OF MONO- AND DIACETYLENIC HYDROXAMIC ACIDS
Gorodetskova, N. R.,Klebanov, B. M.,Loginova, N. A.,Radchenko, O. A.,Il'chenko, A. Ya.
, p. 740 - 743 (1990)
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Designing and synthesis of novel antimicrobial heterocyclic analogs of fatty acids
Ahmad, Aiman,Ahmad, Anis,Varshney, Himani,Rauf, Abdul,Rehan, Mohd,Subbarao, Naidu,Khan, Asad U.
, p. 887 - 900 (2013)
Novel series of long chain isoxazole derivatives were designed as inhibitors of Cytochrome P450-14DM14a-demethylase from Candida albicans and ribosomal subunit of S12 protein from Escherichia coli. The novel compounds (6-10) were synthesized through 1,3-dipolar cycloaddition of nitrile oxide to long chain alkynoic acid and alkenyl/hydroxyalkenyl esters and tested for their antimicrobial activity by disk diffusion assay and MIC by broth micro dilution method. After predicting the hidden potential and drug-likeness of compounds, ADMET-related descriptors were also calculated to predict pharmacokinetic properties. Molecular docking studies have been performed to evaluate possible mode of action of molecules in active site of receptor. Compounds (9 and 10) showed excellent antimicrobial activity nearly equivalent to the control compounds.
Kinetics of epoxidation of alkyl esters of undecylenic acid: Comparison of traditional routes vs. Ishii-Venturello chemistry
Yadav,Satoskar
, p. 397 - 407 (1997)
Epoxidation of undecylenic acid and its methyl and ethyl esters with aqueous H2O2 was carried out by using different traditional routes, ion exchange resin, and the newly developed synergistic usage of heteropoly acids and phase transfer catalysis in a biphasic system. The so-called Ishii-Venturello chemistry was employed to develop a kinetic model. Interesting selectivities are obtained.
Synthesis of fully alternating polycarbonate with low Tg from carbon dioxide and bio-based fatty acid
Zhang, Ying-Ying,Zhang, Xing-Hong,Wei, Ren-Jian,Du, Bin-Yang,Fan, Zhi-Qiang,Qi, Guo-Rong
, p. 36183 - 36188 (2014)
The selective copolymerization of CO2 and an epoxide to form fully alternating polycarbonates is a great challenge via catalysis with the zinc-cobalt(iii) double metal cyanide complex [Zn-Co(iii) DMCC]. We describe the first perfectly alternating copolymerization of CO2 with a bio-based epoxide. The resultant polycarbonate had a low Tgs of -38 to -44 °C and two end hydroxyl groups, which were then used to initiate ring-opening polymerization of l-lactide via metal-free catalysis, affording a biodegradable triblock copolymer. This study provides a new platform copolymer for making various advanced polymers with biodegradable properties. This journal is the Partner Organisations 2014.
Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes
Martínez, Javier,de la Cruz-Martínez, Felipe,Martínez de Sarasa Buchaca, Marc,Fernández-Baeza, Juan,Sánchez-Barba, Luis F.,North, Michael,Castro-Osma, José A.,Lara-Sánchez, Agustín
, p. 460 - 468 (2021/04/06)
Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.
Methyl Radical Initiated Kharasch and Related Reactions
Tappin, Nicholas D. C.,Renaud, Philippe
supporting information, p. 275 - 282 (2020/12/07)
An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).
Cobalt-Catalyzed C(sp2)-H Allylation of Biphenyl Amines with Unbiased Terminal Olefins
Baccalini, Alessio,Vergura, Stefania,Dolui, Pravas,Maiti, Siddhartha,Dutta, Subhabrata,Maity, Soham,Khan, Farheen Fatima,Lahiri, Goutam Kumar,Zanoni, Giuseppe,Maiti, Debabrata
supporting information, p. 8842 - 8846 (2019/11/11)
Unactivated olefins usually react poorly in conventional alkenylation reactions. Their introduction via C-H activation is limited to aromatic acids. Herein, we disclose a C-H functionalization protocol of aromatic amines with unactivated olefins, which shows exclusive allylic selectivity for the distal ring of the biphenyl system by exploiting a readily available cobalt(II) catalyst. The allylation proceeds smoothly involving a broad set of unbiased olefins and biaryls, giving access to the functionalization of the biphenyl scaffold.
