5695-95-4Relevant academic research and scientific papers
Base-Mediated Cascade Aldol Addition and Fragmentation Reactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling Chemodivergence via Choice of Base, Solvent, and Substituents
Ward, George,Liotta, Charles L.,Krishnamurthy, Ramanarayanan,France, Stefan
supporting information, p. 14219 - 14233 (2018/10/24)
The diester derivative of dihydroxyfumaric acid (DHF) has been used exclusively as an electrophile in organic synthesis. However, the synthetic utility of DHF's nucleophilic reactivity, contained in the ene-diol moiety, has been underexplored. Inspired by recently observed pH-dependent chemodivergent nucleophilic aldol reactions of dihydroxyfumarate (DHF2-) with glyoxylate and formaldehyde, we report herein the control and synthetic application of base-controlled chemodivergent reactions between dihydroxyfumarate and aromatic and heteroaromatic aldehydes. With hydroxide as the base in a predominantly aqueous medium, aldol addition followed by deoxalation occurs to provide various 3-aryl-2,3-dihydroxypropanoic acids. With triethylamine as the base in THF, 1-aryl-2,3-dihydroxypropanones are the products of the reaction. In order to understand the difference in reactivity between DHF, its dicarboxylate, and its dimethyl ester, we undertook computational and experimental studies that provide a rationale as to why the dihydroxyfumarate (DHF2-) is a nucleophile while the corresponding diester reacts as an electrophile.
Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations
Narasimhan, Balasubramanian,Belsare, Deepak,Pharande, Devayani,Mourya, Vishnukant,Dhake, Avinash
, p. 827 - 834 (2007/10/03)
A series of esters (Ia-k), substituted derivatives (II a-d) and amides (IIIa-q) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds If and IIc proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives Ia-k, II a-d and IIIa-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.
Reactions of Trialkylsilyl Trifluoromethanesulfonates VII. - α-Trimethylsiloxycarboxylation by Tris(trimethylsiloxy)ethene.
Oesterle, Thomas,Simchen, Gerhard
, p. 693 - 700 (2007/10/02)
In the presence of trimethylsilyl triflate (1), acetals and orthocarboxylic acid esters 3 react with tris(trimethylsiloxy)ethene 2 to yield 3-alkoxy- and 3,3-dialkoxy-2-(trimethylsiloxy)carboxylates 4.From carbonyl compounds 6 and the ketene acetal 2 2,3-
Kinetics and Mechanism of the Oxidation of Unsaturated Carboxylic Acids by Methyltributylammonium Permanganate in Methylene Chloride Solutions
Perez-Benito, Joaquin F.,Lee, Donald G.
, p. 3239 - 3243 (2007/10/02)
The product obtained when permanganate is reduced by unsaturated carboxylic acids under anhydrous conditions is manganese(III).The rate of reaction, which is subject to acid catalysis, exhibits a Hammet ρ value of 1.11 and inverse secondary isotope effects (kH/kD = 0.96-0.98) when the hydrogens on the double bond are replaced by deuterium.The involvement of a free-radical process is indicated by the formation of polymer during the oxidation of acrylic and methacrylic acids.The reaction is believed to be initiated by formation of an organometallic complex in which the double bond is a η2 ligand on manganese.Rearrangement of this complex results in the formation of a reactive manganate(V) cyclic diester, which undergoes a rapid (free-radical) reduction to manganese(III).
