375-01-9Relevant articles and documents
Engineering Catalysts for Selective Ester Hydrogenation
Dub, Pavel A.,Batrice, Rami J.,Gordon, John C.,Scott, Brian L.,Minko, Yury,Schmidt, Jurgen G.,Williams, Robert F.
, p. 415 - 442 (2020/03/04)
The development of efficient catalysts and processes for synthesizing functionalized (olefinic and/or chiral) primary alcohols and fluoral hemiacetals is currently needed. These are valuable building blocks for pharmaceuticals, agrochemicals, perfumes, and so forth. From an economic standpoint, bench-stable Takasago Int. Corp.'s Ru-PNP, more commonly known as Ru-MACHO, and Gusev's Ru-SNS complexes are arguably the most appealing molecular catalysts to access primary alcohols from esters and H2 (Waser, M. et al. Org. Proc. Res. Dev. 2018, 22, 862). This work introduces economically competitive Ru-SNP(O)z complexes (z = 0, 1), which combine key structural elements of both of these catalysts. In particular, the incorporation of SNP heteroatoms into the ligand skeleton was found to be crucial for the design of a more product-selective catalyst in the synthesis of fluoral hemiacetals under kinetically controlled conditions. Based on experimental observations and computational analysis, this paper further extends the current state-of-the-art understanding of the accelerative role of KO-t-C4H9 in ester hydrogenation. It attempts to explain why a maximum turnover is seen to occur starting at 25 mol % base, in contrast to only 10 mol % with ketones as substrates.
A process for the preparation of the fluoro method
-
Paragraph 0024, (2017/06/29)
The invention relates to a method of preparing fluoroalcohol of which the structure formula is F3C(CF2)nCH2OH, wherein n is an integer of 2-8. The method includes following steps: (I) mixing fluorocarboxylic acid and isopropyl alcohol and performing a temperature-increasing reflux reaction; (II) when the reaction is finished, distilling the reaction liquid to remove generated water and isopropyl alcohol, and cooling the rest reaction liquid to room temperature; (III) pouring the reaction liquid into distillated water, regulating the pH value to 6.5-7 by an alkali liquid, allowing the reaction liquid to stand to layer the reaction liquid to obtain an organic layer; (IV) removing water from the organic layer to obtain fluorocarboxylic isopropyl ester; (V) adding the fluorocarboxylic isopropyl ester and a solvent into a high-pressure reaction kettle with addition of a hydrogenation catalyst and a co-catalyst, sealing the reaction kettle, increasing the temperature and filling hydrogen to a high pressure for performing a reaction for 20-60 h; (VI) when the reaction is finished, cooling the reaction kettle to room temperature, discharging hydrogen to obtain a reaction mixed liquid; (VII) performing rectification to the reaction mixed liquid to separate the solvent, cooling the rest liquid and pouring the rest liquid into distillated water and regulating the pH value to 6.5-7 by an acid liquid; and (VIII) allowing the mixed liquid to stand to layer the mixed liquid to obtain an organic layer, removing water from the organic layer and distilling the organic layer to obtain the corresponding fluoroalcohol.
Incorporation of a 3-(2,2,2-Trifluoroethyl)-γ-hydroxy-γ-lactam motif in the side chain of 4-aminoquinolines. Syntheses and antimalarial activities
Cornut, Damien,Lemoine, Hugues,Kanishchev, Oleksandr,Okada, Etsuji,Albrieux, Florian,Beavogui, Abdoul Habib,Bienvenu, Anne-Lise,Picot, Stéphane,Bouillon, Jean-Philippe,Médebielle, Maurice
, p. 73 - 83 (2013/02/23)
In this paper we report the synthesis and antimalarial properties of two series of fluoroalkylated γ-lactams derived from 4-aminoquinoline as potent chemotherapeutic agents for malaria treatment. These molecules obtained in several steps resulted in the identification of very potent structures with in vitro activity against Plasmodium falciparum clones of variable sensitivity (3D7 and W2) in the range of 19-50 nM with resistance indices in the range of 1.0-2.5. In addition, selected molecules (50, 51, 58, 60, 63, 70, 72, 74, 78, 81, 84, and 87) that are representative of the two series of compounds did not show cytotoxicity in vitro when tested against human umbilical vein endothelial cells up to a concentration of 100 μM. The most promising compounds (82 and 84) showed significant IC50 values close to 26 and 19 nM against the chloroquino-sensitive strain 3D7 and 49 and 42 nM against the multi-drug-resistant strain W2. Furthermore, two model compounds (50 and 70) were found to be quite stable over 48 h at pH 7.4 and 5.2. Overall, our preliminary data indicate that this class of structures contains promising candidates for further study.