614-44-8Relevant academic research and scientific papers
Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant
Targel, Tom,Ramesh, Palakuri,Portnoy, Moshe
supporting information, p. 3017 - 3021 (2018/06/27)
Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.
Reactions of peroxide products of ozonolysis of allyl ethers/esters in the AcOH-CH2Cl2 system on treatment with semicarbazide hydrochloride
Raskil'dina, Gulnara Z.,Legostaeva, Yuliya V.,Garifullina, Liliya R.,Sultanova, Rimma M.,Ishmuratov, Gumer Y.,Zlotskii, Simon S.
, p. 652 - 656 (2017/01/13)
Background: A one-pot method for the preparation of the corresponding alkoxy acetic acids by low-temperature ozonolysis of allyl ethers/esters followed by treatment with semicarbazide hydrochloride has been suggested. The reaction occurs via formation of acetoxyhydroperoxide, subsequent reduction of which depends on the process temperature and the nature of the starting substrate. Objective: The article is aimed at the development of one-pot method for obtaining practically important alkoxy acetic acids, because the ozonolytic cleavage of a ?=? double bond is the key step in full syntheses of many biologically active compounds. Methods: We used a low temperature ozonolysis of functionally substituted olefins in the system acetic acid-methylene dichloride followed by reduction of semicarbazide hydrochloride. To create a method we have used available allyl ethers/esters as starting materials. Results: We investigated reaction of the peroxide products of ozonolysis of monoallyl ethers, ester and diallyl ethers in an AcOH/CH2Cl2 mixture on treatment with semicarbazide hydrochloride at various temperatures. We have discovered that the selectivity of reduction of acetoxyhydroperoxide formed at the first stage depends both on the process temperature and on the nature of the starting substrate. A decrease in temperature favors acid hydrolysis and formation of a carboxylic acid. Conclusion: We have proposed a simple and highly efficient one-pot method for the preparation alkoxy acetic acids without isolation of intermediate peroxides.
IMIDAZO(1,2-a)PYRIDINE DERIVATIVE
-
Page 128, (2010/02/09)
A compound reprsented by the following formula (I), its salts or nsolvates thereof capable of specifically or selectively expressig an antifungal activity in a broad spectrum based on the novel mechanism thereof of 1,6-β-glucan synthesis inhibition, and an antifungal agent containing any of them.
Inhibition of peptidylglycine α-amidating monooxygenase by exploitation of factors affecting the stability and ease of formation of glycyl radicals
Barratt, Brendon J. W.,Easton, Christopher J.,Henry, David J.,Li, Iris H. W.,Radom, Leo,Simpson, Jamie S.
, p. 13306 - 13311 (2007/10/03)
Peptidylglycine α-amidating monooxygenase catalyzes the biosynthesis of peptide hormones through radical cleavage of the C-terminal glycine residues of the corresponding prohormones. We have correlated ab initio calculations of radical stabilization energies and studies of free radical brominations with the extent of catalysis displayed by peptidylglycine α-amidating monooxygenase, to identify classes of inhibitors of the enzyme. In particular we find that, in closely related systems, the substitution of glycolate for glycine reduces the calculated radical stabilization energy by 34.7 kJ mol -1, decreases the rate of bromination with N-bromosuccinimide at reflux in carbon tetrachloride by a factor of at least 2000, and stops catalysis by the monooxygenase, while maintaining binding to the enzyme.
The Effect of pH Control on the Selective Ruthenium-Catalyzed Oxidation of Ethers and Alcohols with Sodium Hypochlorite
Gonsalvi, Luca,Arends, Isabel W. C. E.,Moilanen, Pasi,Sheldon, Roger A.
, p. 1321 - 1328 (2007/10/03)
Highly selective oxidations of ethers to esters or lactones and of secondary alcohols to ketones were achieved using catalytic amounts of various Ru precursors and the theoretical amount of NaOCl. Reactions were carried out in biphasic solvent mixtures at constant pH 9-9.5 via either feed-on-demand addition of HCl and NaOH or in the presence of NaHCO3/Na 2CO3 buffer. The catalyst could be easily recycled for at least 4 times with only minor loss in selectivity. Products were generally recovered by simple phase separation and evaporation of the organic solvent. The effects of catalyst precursor, additives and pH control method are also described.
Prodrug derivatives of carboxylic acid drugs
-
, (2008/06/13)
Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.
Glycolate ester peracid precursors
-
, (2008/06/13)
The invention provides novel bleaching compositions comprising peracid precursors with the general structure STR1 with R, R', R" and L as defined in the specification. Novel peracids and precursors are also herein disclosed. These peracid precursors provide new, proficient and cost-effective compounds for fabric bleaching.
Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion, and physicochemical properties.
Nielsen,Bundgaard
, p. 285 - 298 (2007/10/02)
Benzoic acid esters of various substituted 2-hydroxyacetamides (glycolamides) were found to be hydrolyzed extremely rapidly in human plasma solutions, the half-lives of hydrolysis being less than 5 s in 50% plasma solutions for some N,N-disubstituted glycolamide esters. The rapid rate of hydrolysis could be largely attributed to cholinesterase (also called pseudocholinesterase) present in plasma. From a study of a variety of substituted glycolamide esters and structurally related esters, the most prominent structural requirement needed for a rapid rate of hydrolysis was found to be the glycolamide ester structure combined with the presence of two substituents on the amide nitrogen atom. A structural similarity of such esters with benzoylcholine, a good substrate for cholinesterase, was put forward. Esters of N,N-disubstituted glycolamides are suggested to be a useful biolabile prodrug type for several carboxylic acid agents. The esters combine a high susceptibility to undergo enzymatic hydrolysis in plasma with a high stability in aqueous solution. Furthermore, as demonstrated with the benzoic acid model esters, it is feasible to obtain ester derivatives with almost any desired water solubility or lipophilicity with retainment of marked lability to enzymatic hydrolysis.
Anodic Oxidation of O-Benzoylated α-Hydroxyacetic Acids Concerning the Structure of the Cationic Intermediate
Thomas, H. Guenter,Kessel, Stephan,Mueller, Edwin
, p. 2173 - 2177 (2007/10/02)
Anodic oxidation of (benzoyloxy)acetic acid (1b) at graphite electrodes in methanol leads to the substitution product methoxymethyl benzoate (3) as well as the fragmentation product methyl benzoate (4) recovering all labeled oxygen in the carbonyl groups.This result proves that the 1,3-dioxetanylium ion 2' is not involving in the non-Kolbe electrolysis of O-benzoylated α-hydroxyacetic acids.The cationic intermediate 2 is of open-chain structure.
SENSITIZED PHOTOOXIDATION OF 2,5-FURANYLDIMETHYL DIBENZOATE
Kuo, Yueh-Hsiung,Shieh, Chir-Jeng
, p. 1271 - 1274 (2007/10/02)
Sensitized photooxidation of 2,5-furanyldimethyl dibenzoate was carried out in acetonitrile and methanol respectively.Two products 3 and 6 were obtained via O,O-diradical intermediate 15 which was discovered from ozonide for the first time.
