61415-12-1Relevant academic research and scientific papers
Lipophilic NHC assisted one-pot synthesis of syncarpamide analogues in aqueous medium
Suresh, Pavithira,Selva Ganesan, Subramaniapillai
supporting information, p. 6257 - 6261 (2019/04/25)
Lipophilic NHC catalysis in aqueous medium was reported for the synthesis of biologically relevant (a)symmetrically substituted and unsymmetrically substituted syncarpamide analogues. All the reported reactions were performed in the absence of any expensive metal salts or additives. A diverse array of syncarpamide analogues was obtained in good yields. Lipophilic NHC catalysis was also extended to chemoselective transesterification reactions.
Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates
Menezes, Jose C.J.M.D.S.,Kamat, Shrivallabh P.,Cavaleiro, Jose A.S.,Gaspar, Alexandra,Garrido, Jorge,Borges, Fernanda
experimental part, p. 773 - 777 (2011/03/19)
Long chain alkyl hydroxycinnamates (8-21) were synthesized from the corresponding half esters of malonic acid (5-7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated usin
Synthesis and DNA polymerase α and β inhibitory activity of alkyl p-coumarates and related compounds
Nishimura, Katsumi,Takenaka, Yukiko,Kishi, Manami,Tanahashi, Takao,Yoshida, Hiromi,Okuda, Chiaki,Mizushina, Yoshiyuki
experimental part, p. 476 - 480 (2009/12/28)
trans- and cis-Icosyl, docosyl, and tetracosyl p-coumarates, constituents of Artemisia annua L., and their structurally-related compounds were synthesized and evaluated for inhibitory activity on DNA polymerases α and β. Among 30 compounds synthesized, oc
Nucleophilic acyl substitutions of esters with protic nucleophiles mediated by amphoteric, oxotitanium, and vanadyl species
Chen, Chien-Tien,Kuo, Jen-Huang,Ku, Cheng-Hsiu,Weng, Shiue-Shien,Liu, Cheng-Yuan
, p. 1328 - 1339 (2007/10/03)
(Chemical Equation Presented) A diverse array of oxometallic species were examined as catalysts in nucleophilic acyl substitution (NAS) reactions of methyl (or ethyl) esters with protic nucleophiles. Among them, oxotitanium acetylacetonate (TiO(acac)2) and vanadyl chloride (VOCl 2-(THF)x) served as the most efficient and water-tolerant catalysts. Transesterifications of methyl and/or ethyl esters with functionalized (including acid- or base-sensitive) 1° and 2° alcohols can be carried out chemoselectively in refluxed toluene or xylene in a 1:1 substrate stoichiometry using 1 mol % catalyst loading. The resultant products were furnished in 85-100% yields by simple aqueous workup to remove water-soluble catalysts. The new NAS protocol is also amenable to amines and thiols in 74-91% yields, albeit with higher loading (2.5 equiv) of protic nucleophiles. Representative examples of commercial interests such as Padimate O and antioxidant additives for plastics were also examined to demonstrate their practical applications. A 1:1 adduct between TiO(acac)2 and a given 1-octadecanol was identified as (C18H37O) 2Ti(acac)2 and was responsible for its subsequent NAS of methyl esters.
Liquid-Crystalline Solvents as Mechanistic Probes. 20. Crystalline and Smectic B Solvent Control over the Selectivity of Photodimerization of n-Alkyl Cinnamates
Ramesh, Varadaray,Weiss, Richard G.
, p. 2535 - 2539 (2007/10/02)
The photodimerizations of n-octadecyl, n-hexadecyl, and n-tetradecyl esters of trans-cinnamic acid have been investigated in the crystalline, smectic B, and isotropic phases of n-butyl stearate.A strong preference for head-to-tail dimerization is found in the ordered solvent phases.Dipole-dipole-induced interactions between cinnamates and solvent-mediated solute alignments are the factors that combine to control the regioselectivity of photodimerization.The ability of cinnamate esters to be incorporated into the ordered solvent phases is extremely dependent upon the length of the n-alkyl solute chains.However, ease of incorporation has little influence upon regioselectivity.
