120677-74-9Relevant academic research and scientific papers
Improved method for preparing (Z, E)-12-tetradecene-1-alcohol acetate
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Paragraph 0034-0036; 0045-0047; 0056-0058, (2021/03/31)
The invention provides an improved method for preparing (Z, E)-12-tetradecene 1-alcohol acetate, which innovatively introduces a three-solvent system into a solvent system in wittig reaction, increases the solubility of the reagent in the reaction system, lowers the overall freezing point of the solvent, avoids the agglomeration phenomenon at lower temperature in the reaction process under dual actions, and unsmooth reaction stirring and generation of a large number of impurities are avoided, so that the post-treatment difficulty is increased; glacial acetic acid is used for terminating the reaction and replacing previous water-containing dilute acid, condensation of residual aldehydes in the raw materials is controlled, generation of a large number of impurities is avoided, and once a condensation product generates p-triphenylphosphine oxide and a main product enol which are high in solubility and cannot be separated, the aftertreatment difficulty can be greatly enhanced, and the product extraction loss is large; and meanwhile, the reaction can be carried out in a homogeneous state at about 0 DEG C, so that the conversion is thorough, the yield is greatly improved, the post-treatment is simple, the byproduct triphenoxyphosphine is separated out in a granular form, and a large amount of muddy wastes and other solid wastes are avoided.
Linking 7-Nitrobenzo-2-oxa-1,3-diazole (NBD) to Triphenylphosphonium Yields Mitochondria-Targeted Protonophore and Antibacterial Agent
Iaubasarova,Khailova,Nazarov,Rokitskaya,Silachev,Danilina,Plotnikov,Denisov,Kirsanov,Korshunova,Kotova,Zorov,Antonenko
, p. 1578 - 1590 (2020/12/30)
Abstract: Appending lipophilic cations to small molecules has been widely used to produce mitochondria-targeted compounds with specific activities. In this work, we obtained a series of derivatives of the well-known fluorescent dye 7-nitrobenzo-2-oxa-1,3-
Synthesis method for sex pheromone of ostriniafurnacalis
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Paragraph 0071; 0080; 0082; 0083; 0092; 0094; 0095; 0104, (2020/05/19)
The invention discloses a synthesis method for a sex pheromone of ostriniafurnacalis, namely a (Z, E)-12-tetradecen-1-ol acetate compound. The synthesis method comprises the following steps: firstly,performing a reaction on 1, 12-dibromododecane and triphenylphosphine to produce omega-bromododecyltriphenylphosphonium bromide, then performing a reaction on the omega-bromododecyltriphenylphosphonium bromide and aldehyde under the action of organic alkali sodium dimethyl sulfoxide to produce Z-main type omega-bromotetradecene, then hydrolyzing by alkali metal hydroxide to obtain Z-main type (Z,E)-12-tetradecen-1-ol, performing an acetylation reaction on the (Z, E)-12-tetradecen-1-ol and acetic anhydride to obtain Z-main type(Z, E)-12-tetradecen-1-ol acetate, and performing an isomer conversion reaction on the Z-main type(Z, E)-12-tetradecen-1-ol acetate and a sodium nitrite and nitric acid solution to obtain E-main type(Z, E)-12-tetradecen-1-ol acetate. With the synthesis method, few side reactions occur in the synthesis process and the product purity is high.
Synthesis and biological characterization of new aminophosphonates for mitochondrial pH determination by 31P NMR spectroscopy
Culcasi, Marcel,Casano, Gilles,Lucchesi, Céline,Mercier, Anne,Clément, Jean-Louis,Pique, Valérie,Michelet, Laure,Krieger-Liszkay, Anja,Robin, Maxime,Pietri, Sylvia
, p. 2487 - 2499 (2013/05/22)
A series of mitochondria targeted α-aminophosphonates combining a diethoxyphosphoryl group and an alkyl chain-connected triphenylphosphonium bromide tail were designed and synthesized, and their pH-sensitive 31P NMR properties and biological activities in vitro and in vivo were evaluated. The results showed a number of these mito-aminophosphonates exhibiting pKa values fitting the mitochondrial pH range, short relaxation, and chemical shift parameters compatible with sensitive 31P NMR detection, and low cytotoxicity on green algae and murine fibroblasts cell cultures. Of these, two selected compounds demonstrated to distribute at NMR detectable levels within the cytosolic and mitochondrial sites following their perfusion to isolated rat livers, with no detrimental effects on cell energetics and aerobic respiration. This study provided a new molecular scaffold for further development of in situ spectroscopic real-time monitoring of mitochondrion/cytosol pH gradients.
