5024-21-5Relevant articles and documents
Efficient Palladium-Catalyzed Carbonylation of 1,3-Dienes: Selective Synthesis of Adipates and Other Aliphatic Diesters
Yang, Ji,Liu, Jiawang,Ge, Yao,Huang, Weiheng,Ferretti, Francesco,Neumann, Helfried,Jiao, Haijun,Franke, Robert,Jackstell, Ralf,Beller, Matthias
supporting information, p. 9527 - 9533 (2021/03/08)
The dicarbonylation of 1,3-butadiene to adipic acid derivatives offers the potential for a more cost-efficient and environmentally benign industrial process. However, the complex reaction network of regioisomeric carbonylation and isomerization pathways, make a selective and direct transformation particularly difficult. Here, we report surprising solvent effects on this palladium-catalysed process in the presence of 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, which allow adipate diester formation from 1,3-butadiene, carbon monoxide, and methanol with 97 % selectivity and 100 % atom-economy under scalable conditions. Under optimal conditions a variety of di- and triesters from 1,2- and 1,3-dienes can be obtained in good to excellent yields.
Discovery and Pharmacological Studies of 4-Hydroxyphenyl-Derived Phosphonium Salts Active in a Mouse Model of Visceral Leishmaniasis
Manzano, José Ignacio,Cueto-Díaz, Eduardo J.,Olías-Molero, Ana Isabel,Perea, Ana,Herraiz, Tomás,Torrado, Juan J.,Alunda, José María,Gamarro, Francisco,Dardonville, Christophe
, p. 10664 - 10675 (2019/12/04)
We report the discovery of new 4-hydroxyphenyl phosphonium salt derivatives active in the submicromolar range (EC50 from 0.04 to 0.28 μM, SI > 10) against the protozoan parasite Leishmania donovani. The pharmacokinetics and in vivo oral efficacy of compound 1 [(16-(2,4-dihydroxyphenyl)-16-oxohexadecyl)triphenylphosphonium bromide] in a mouse model of visceral leishmaniasis were established. Compound 1 reduced the parasite load in spleen (98.9%) and liver (95.3%) of infected mice after an oral dosage of four daily doses of 1.5 mg/kg. Mode of action studies showed that compound 1 diffuses across the plasma membrane, as designed, and targets the mitochondrion of Leishmania parasites. Disruption of the energetic metabolism, with a decrease of intracellular ATP levels as well as mitochondrial depolarization together with a significant reactive oxygen species production, contributes to the leishmanicidal effect of 1. Importantly, this compound was equally effective against antimonials and miltefosine-resistant clinical isolates of Leishmania infantum, indicating its potential as antileishmanial lead.
Metal/bromide autoxidation of triglycerides for the preparation of FAMES to improve the cold-flow characteristics of biodiesel
Phung, Peter,Rowlands, William N.,Thiyakesan, Appadurai,Benndorf, Paul,Masters, Anthony F.,Maschmeyer, Thomas
, p. 162 - 168 (2014/07/07)
Triglyceride autoxidation using a homogeneous Co/Mn/Zr/bromide catalyst in acetic acid (93%) of low grade tallow, canola oil or soy bean oil in a batch reactor at 150 °C for 2 h, produced lower molecular weight products relative to the fatty acids of the starting triglycerides. For the autoxidation of tallow the main products after esterification were monoesters Me(CH 2)mC(O)OMe (m = 5-12) and diesters MeOC(O)(CH 2)nC(O)OMe, (n = 7-12). Oxidation of the saturated fatty acids in triglycerides was confirmed and modelled using methyl palmitate. Post-treatment esterification of tallow autoxidation products to produce biodiesel (BD) esters resulted in improved cold temperature properties by a mean of 13.0 °C, i.e. a mean cloud point (CP) 1.0 °C (cf. unmodified tallow biodiesel: CP 14 °C).
Improved Syntheses of Benzyl Hydraphile Synthetic Cation-Conducting Channels
Curvey, Nichole S.,Luderer, Sarah E.,Walker, John K.,Gokel, George W.
, p. 2771 - 2779 (2015/02/19)
The tris(macrocycle)s that function in bilayer membranes as ion channels have recently shown versatile new applications such as antibiotic synergists and as agents for direct injection chemotherapy. This report records the development of new and versatile approaches to these molecules that produce significantly better overall yields for a group of previously reported hydraphiles having spacer chains ranging from octylene to hexadecylene.
Cycloalkane-based thermomorphic systems for organic electrochemistry: An application to Kolbe-coupling
Okada, Yohei,Kamimura, Kazuya,Chiba, Kazuhiro
supporting information; experimental part, p. 5857 - 5862 (2012/09/08)
The discovery that cycloalkanes can form thermomorphic systems with typical polar organic solvents has led to the development of less-polar electrolyte solutions. Their mixing and separation can be regulated reversibly at a moderate temperature range. The phase switching temperature can be controlled by changing the solvent compositions. While biphasic conditions are maintained below the phase switching temperature, conductive monophasic conditions as less-polar electrolyte solutions are obtained above the phase switching temperature. After the electrochemical transformations, biphasic conditions are reconstructed below the phase switching temperature, facilitating the separation of cycloalkane where hydrophobic products or designed hydrophobic platforms are selectively partitioned. Several polar organic solvents, including acetonitrile, methanol, and pyridine, can be used in this system according to the requirement of the reactions.
General synthesis and aggregation behaviour of a series of single-chain 1,ω-Bis(phosphocholines)
Drescher, Simon,Meister, Annette,Blume, Alfred,Karlsson, Goeran,Almgren, Mats,Dobner, Bodo
, p. 5300 - 5307 (2008/02/11)
The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).
On the search of new I2-IBS aliphatic ligands: Bis-guanidino carbonyl derivatives
Corcoran, Jonathan,Rodriguez, Fernando,Rozas, Isabel,Meana, J. Javier,Callado, Luis F.
, p. 6009 - 6012 (2008/09/16)
Continuing with our search of aliphatic dicationic derivatives as I2-IBS ligands and looking at Amiloride, a known ligand of I2-IBS, we have incorporated the guanidinocarbonyl moiety into our aliphatic compounds with the intention of improving the binding to I2-IBS. Thus, we present the different approaches to the preparation and pharmacological evaluation (in human brain tissue) as I2-IBS ligands of a new series of aliphatic derivatives incorporating the guanidinocarbonyl group and with different chain length (n = 8-12, and 14 methylene groups).
Dispiro-1,2,4-trioxolanes by Ozonolysis of Cycloalkylidenecycloalkanes on Polyethylene
Griesbaum, Karl,Krieger-Beck, Petra,Beck, Johannes
, p. 391 - 396 (2007/10/02)
Ozonolyses of symmetrical (1b-d) and of unsymmetrical cycloalkylidenecycloalkanes (8a, b) afforded the dispiro-1,2,4-trioxolanes 4b-d and 9a, b, respectively.Their thermal decompositions gave mixtures of the cyclic ketones (3) and lactones (6).Photolysis afforded in addition to 3 and 6 the cyclic anhydrides 13, which are isomeric with the corresponding disoiro-1,2,4-trioxolanes.
Syntheses d'amidoesters par reaction de Kolbe
Abderrahman, Ben Moufida,Laurent, Eliane,Marquet, Bernard
, p. 571 - 578 (2007/10/02)
The synthesis of amidoesters has been investigated by anodic cooxidation of diacid hemiesters CO2H-CH2-Z-CO2CH3 -CH2-> and amidoacids R1-N(Y)-(CH2)2-CO2H .The scope of this reaction was examined in detail.This synthetic pathway provided very a simple access to a wide range of amidoesters R1-N(Y)-(CH2)3-Z-CO2CH3 by varying Z and R1 as well as n value.
Bifunctional compounds from reaction of alkoxy hydroperoxides with metal salts
Cardinale,Laan,Van Der Steen,Ward
, p. 6051 - 6054 (2007/10/02)
Alkoxy hydroperoxides, obtained by ozonizing olefins in alcoholic solution, were treated with ferrous sulfate. C-C bond scission and radical formation was followed by dimerization of the radicals formed. Ozonides reacted similarly. Acyclic and cyclic olefins, including a cyclic enol ether, gave rise to a range of α,ω-disubstituted products in modest yields. By using ferric chloride, ω-chloro esters were obtained from the alkoxy hydroperoxides derived from olefinic esters.
