4567-98-0Relevant 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.
Two-way homologation of aliphatic aldehydes: Both one-carbon shortening and lengthening via the same intermediate
Yoo, Jae Won,Seo, Youngran,Park, Jong Beom,Kim, Young Gyu
, (2020/01/13)
Aliphatic aldehydes can be homologated to both one-carbon shorter and one-carbon longer homologous carbonyl compounds through the 2–4 steps of reactions via the same intermediates, β,γ-unsaturated α-nitrosulfones, prepared from the proline-catalyzed sequential reactions of several aliphatic aldehydes with phenylsulfonylnitromethane. While the oxidative cleavage of the key intermediates gave one-carbon less homologous carbonyl compounds, the reduction of the same key intermediates followed by an oxidation produced one-carbon more homologous carbonyl compounds.
Lipoteichoic acid anchor triggers Mincle to drive protective immunity against invasive group A Streptococcus infection
Imai, Takashi,Matsumura, Takayuki,Mayer-Lambertz, Sabine,Wells, Christine A.,Ishikawa, Eri,Butcher, Suzanne K.,Barnett, Timothy C.,Walker, Mark J.,Imamura, Akihiro,Ishida, Hideharu,Ikebe, Tadayoshi,Miyamoto, Tomofumi,Ato, Manabu,Ohga, Shouichi,Lepenies, Bernd,Van Sorge, Nina M.,Yamasaki, Sho
, p. E10662 - E10671 (2018/11/20)
Group A Streptococcus (GAS) is a Gram-positive bacterial pathogen that causes a range of diseases, including fatal invasive infections. However, the mechanisms by which the innate immune system recognizes GAS are not well understood. We herein report that the C-type lectin receptor macrophage inducible C-type lectin (Mincle) recognizes GAS and initiates antibacterial immunity. Gene expression analysis of myeloid cells upon GAS stimulation revealed the contribution of the caspase recruitment domain-containing protein 9 (CARD9) pathway to the antibacterial responses. Among receptors signaling through CARD9, Mincle induced the production of inflammatory cytokines, inducible nitric oxide synthase, and reactive oxygen species upon recognition of the anchor of lipoteichoic acid, monoglucosyldiacylglycerol (MGDG), produced by GAS. Upon GAS infection, Mincle-deficient mice exhibited impaired production of proinflammatory cytokines, severe bacteremia, and rapid lethality. GAS also possesses another Mincle ligand, diglucosyldiacylglycerol; however, this glycolipid interfered with MGDG-induced activation. These results indicate that Mincle plays a central role in protective immunity against acute GAS infection.
Synthetic method of 1,9-diaminononane
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Paragraph 0056; 0058; 0059, (2018/11/22)
The invention provides a synthetic method of 1,9-diaminononane. The method comprises the following steps: firstly, carrying out condensation reaction on undecanoic acid and transforming the undecanoicacid into a derivative of the undecanoic acid; then carrying out ammoniation to generate undecendiamide, and then carrying out Hofmann rearrangement reaction to generate a target product 1,9-diaminononane. The method disclosed by the invention has the advantages that raw materials are inexpensive and easily obtained and have a sufficient supply, and high-temperature and high-pressure reaction conditions are not involved, and a production process has more security. Compared with an abroad production technology, the synthetic method disclosed by the invention has the advantages of less side reaction, high purity of the product, less reaction steps and low requirement on equipment. Compared with a production process reported by domestic companies, the synthetic method has the advantages of less three wastes, and meanwhile, hydrogenation reaction is not involved, and the synthetic method has higher reaction security.
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).
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).
Identification and quantification of aerosol polar oxygenated compounds bearing carboxylic or hydroxyl groups. 1. Method development
Jaoui,Kleindienst,Lewandowski,Edney
, p. 4765 - 4778 (2007/10/03)
In this study, a new analytical technique was developed for the identification and quantification of multifunctional compounds containing simultaneously at least one hydroxyl or one carboxylic group, or both. This technique is based on derivatizing first the carboxylic group(s) of the multifunctional compound using an alcohol (e.g., methanol, 1-butanol) in the presence of a relatively strong Lewis acid (BF3) as a catalyst. This esterification reaction quicldy and quantitatively converts carboxylic acids to their ester forms. The second step is based on silylation of the ester compounds using bis(trimethylsilyl) trifluoroacetamide (BSTFA) as the derivatizing agent. For compounds bearing ketone groups in addition to carboxylic and hydroxyl groups, a third step was used based on PFBHA derivatization of the carbonyls. Different parameters including temperature, reaction time, and effect due to artifacts were optimized. A GC/MS in EI and in methane-CI mode was used for the analysis of these compounds. The new approach was tested on a number of multifunctional compounds. The interpretation of their EI (70 eV) and CI mass spectra shows that critical information is gained leading to unambiguous identification of unknown compounds. For example, when derivatized only with BF3-methanol, their mass spectra comprise primary ions at m/z M .+ + 1, M.+ + 29, and M.- - 31 for compounds bearing only carboxylic groups and M.- + 1, M.+ + 29, M.+ - 31, and M+. - 17 for those bearing hydroxyl and carboxylic groups. However, when a second derivatization (BSTFA) was used, compounds bearing hydroxyl and carboxylic groups simultaneously show, in addition to the ions observed before, ions at m/z M.+ + 73, M .+ - 15, M.+ - 59, M.+ - 75, M.+ - 89, and 73. To the best of our knowledge, this technique describes systematically for the first time a method for identifying multifunctional oxygenated compounds containing simultaneously one or more hydroxyl and carboxylic acid groups.
α-nitrocycloalkanones as a source of α,ω,-dicarboxylic acid dimethyl esters
Ballini, Roberto,Bosica, Giovanna
, p. 16131 - 16138 (2007/10/03)
α,ω-Dicarboxylic acid dimethyl esters arc easily obtained by ring cleavage of α-nitrocycloalkanones. Thus, reaction of the latter compounds with three equivalents of potassium persulfate, in methanol and in presence of sulfuric acid at 80 °C, provides α,ω-dicarboxylic acid dimethyl esters in high yields. Long-chain, and alkylated α,ω-dicarboxylic acid dimethyl esters can be also efficiently obtained.
Dinuclear metal complexes with saturated and unsaturated hydrocarbon bridges
Lindner, Ekkehard,Leibfritz, Thomas,Fawzi, Riad,Steimann, Manfred
, p. 167 - 175 (2007/10/03)
The reaction of the bis(triflates) [Y-(CH2)m-Y] [Y = F3CSO3, m = 4, 6-9, 12, 14, 16 (1a-h)] with the carbonyl metalates M′[M(CO)5] (M′ = Na, K; M = Mn, Re) affords the alkanediyl bridged metal complexes [(OC)5M-(CH2)m-M(CO)5] [m = 6-9, 12, 14, 16; M = Mn (2b-h) and m = 4, 6-9, 12, 14, 16; M = Re (3a-h)]. Starting with K[Mn(CO)5] and the bis(triflates) 1d and 1e the diesters [H3CO(O)C(CH2)mC(O)OCH3] [m = 8, 9 (4d,e)] are obtained in a one-pot reaction. The unsaturated hydrocarbon bridged rhenium complexes trans-[Re]-(CH2)2-CH=CH-(CH2)2-[Re] (6), cis-[Re]-(CH2)3-CH=CH-(CH2)3-[Re] (8), and [Re]-(CH2)p-CH2-C≡C-CH2-(CH2)p-[Re] {[Re] = Re(CO)5, p = 1, 3 (11, 12)} are formed by reaction of the bis(triflates) trans-Y-(CH2)2-CH=CH-(CH2)2-Y (5), cis-Y-(CH2)3-CH=CH-(CH2)3-Y (7), and Y-(CH2)p-CH2-C≡C-CH2-(CH2)p-Y [Y = F3CSO3, p = 1, 3 (9, 10)] with Na[Re(CO)5] in THF. The structure of 8 was determined by an X-ray structural analysis. Crystal data for 8: space group P21/n with a = 12.501(2), b = 6.592(2), c = 26.875(5)A, β = 93.28(2)°, V = 2211.0(9)A3, Z = 4. The structure was refined to R = 0.039, wR = 0.090.
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.
