103-41-3Relevant articles and documents
Synthesis of benzyl esters using 2-benzyloxy-1-methylpyridinium triflate
Tummatorn, Jumreang,Albiniak, Philip A.,Dudley, Gregory B.
, p. 8962 - 8964 (2007)
(Chemical Equation Presented) Triethylamine (Et3N) mediates esterification reactions between the title reagent (1) and carboxylic acids. Alcohols, phenols, amides, and other sensitive functionality are not affected; a dual role for Et3N as a promoter and a scavenger is postulated. Benzyl esters are obtained from substrates including amino acid and sugar derivatives.
METAL-CATALYZED SYNTHESIS OF CARBOXYLIC ESTERS UTILIZING (E)-PHENYL 2-PYRIDYL KETONE O-ACYLOXIMES (PPAO)
Miyasaka, Tadayo,Ishizu, Hidehiro,Sawada, Akihiro,Fujimoto, Akiko,Noguchi, Shunsaku
, p. 871 - 874 (1986)
(E)-Phenyl 2-pyridyl ketone O-acyloximes (PPAO) could be highly activated by metal ions such as Fe(3+), Cu(2+), and Zn(2+), and the most effective catalyst for the synthesis of carboxylic esters was found to be Zn(2+).Furthermore, sterically hindered carboxylic esters were easily obtained utilizing PPAOs and alcoholates in high yields.
A simple one-pot organometallic formylation/trapping sequence using N-formylcarbazole
Dixon, Darren J.,Lucas, Amanda C.
, p. 1092 - 1094 (2004)
Treatment of a range of sp3-, sp2- and sp-nucleophiles with N-formyl carbazole leads to the formation of the metastable anionic carbazole carbinols. In the presence of a second nucleophilic reagent such as phosphonoacetate or an organolithium, these collapse on warming to the aldehyde which is trapped in situ to afford the α,β-unsaturated esters or secondary carbinols respectively.
Protonation of homoenolate equivalents generated by N-heterocyclic carbenes
Maki, Brooks E.,Chan, Audrey,Scheidt, Karl A.
, p. 1306 - 1315 (2008)
Homoenolate equivalents are generated by Lewis basic N-heterocyclic carbene catalysts and then protonated to generate efficiently saturated esters from unsaturated aldehydes. This reactivity is extended to the generation of β-acylvinyl anions from alkynyl aldehydes. The asymmetric protonation of a homoenolate equivalent generated from a β,β-disubstituted aldehyde can be accomplished with a chiral N-heterocyclic carbene. Georg Thieme Verlag Stuttgart.
N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions
Grasa, Gabriela A.,Kissling, Rebecca M.,Nolan, Steven P.
, p. 3583 - 3586 (2002)
(graph presented) Imidazol-2-ylidenes, a family of N-heterocyclic carbones (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl-or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.
N-Methylpyrrolidin-2-one-Promoted Formation of Functional Esters through C–O Bond Cleavage
Liu, Jianming,Wang, Yanyan,Yue, Yuanyuan,Liu, Na,Zhang, Jian,Zhao, Shufang,Tang, Qinghu,Zhuo, Kelei
, p. 2641 - 2647 (2017)
Trifluoromethanesulfonic acid catalyzed C–O bond cleavage leading to the preparation of functional esters in the presence of N-methylpyrrolidin-2-one (NMP) was accomplished. Various substrates were well tolerated, and a gram-scale experiment was successfully realized. DFT calculations indicated that NMP plays a decisive role in accelerating nucleophilic attack of the functional acid to generate the functional esters in chlorobenzene.
Development and Applications of Transesterification Reactions Catalyzed by N-Heterocyclic Olefins
Blümel, Marcus,Noy, Janina-Miriam,Enders, Dieter,Stenzel, Martina H.,Nguyen, Thanh V.
, p. 2208 - 2211 (2016)
A novel method to utilize N-heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocycic carbenes, as organocatalysts to promote transesterification reactions has been developed. Because of their strong Br?nsted/Lewis basicity, NHOs can enhance the nucleophilicity of alcohols for their acylation reactions with carboxylic esters. This transformation can be employed in industrially relevant processes such as the production of biodiesel, the depolymerization of polyethylene terephthalate (PET) from plastic bottles for recycling purposes, and the ring-opening polymerization of cyclic esters to form biodegradable polymers such as polylactide (PLA) and polycaprolactone (PCL).
Synthetic Methods and Reactions; 97. Sulfuryl Chloride Fluoride-Mediated Esterification of Carboxylic Acids with Alcohols
Olah, George A.,Narang, Subhash C.,Garcia-Luna, Armando
, p. 790 - 791 (1981)
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An Exceedingly Efficient and Chemoselective Esterification with Activated Alcohols Using AlCl3/NaI/CH3CN System
Karade,Shirodkar,Potrekar,Karade
, p. 391 - 396 (2004)
A combination of hard Lewis acid AlCl3 and a soft nucleophile NaI in acetonitrile has been used as an efficient system for the selective esterification reaction between aromatic carboxylic acid and alcohol.
Acaricidal activity of tonka bean extracts. Synthesis and structure-activity relationships of bioactive derivatives
Gleye, Christophe,Lewin, Guy,Laurens, Alain,Jullian, Jean-Christophe,Loiseau, Philippe,Bories, Christian,Hocquemiller, Reynald
, p. 690 - 692 (2003)
The acaricidal effects of tonka bean, Dipterix odorata, extracts were investigated on Dermatophagoides pteronyssinus, the European house dust mite, and compared with benzyl benzoate as a standard acaricidal compound. A cyclohexane extract was the most effective, with an EC50 = 0.075 g/m2 after a 24 h period, as compared with benzyl benzoate (0.025 g/m2). Bioassay-guided fractionation of this extract led to the isolation of coumarin (1). Pharmacomodulation of this compound led us to test 20 analogues (2-21), which were either synthesized or purchased.
Water-tolerant and reusable catalysts for direct ester condensation between equimolar amounts of carboxylic acids and alcohols
Nakayama, Masaya,Sato, Atsushi,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 1275 - 1279 (2004)
ZrOCl2 · 8 H2O and HfOCl2 · 8 H2O are highly effective, water-tolerant, and reusable homogeneous catalysts for direct ester condensation be-tween equimolar amounts of carboxylic acids and alcohols. Notably, zirconium(IV) salts such as ZrOCl2 · 8 H2O and Zr(OAc)x(OH)y are potential green catalysts due to their low toxicity, commercial availability at low cost, ease of handling, high catalytic activity, and reusability.
Iodine-catalyzed synthesis of β-uramino crotonic esters as well as oxidative esterification of carboxylic acids in choline chloride/urea: a desirable alternative to organic solvents
Moayyed, Mohammadesmaeil,Saberi, Dariush
, p. 445 - 455 (2021)
Abstract: Iodine-mediated selective synthesis of β-uramino crotonic esters was achieved via the reaction of β-dicarbonyls and urea at room temperature. Choline chloride/urea mixture, as an eco-friendly, cheap, non-toxic, and recyclable deep eutectic solvent (DES), was employed as sustainable media as well as reagent at the same time in these transformations. Some derivatives of β-uramino crotonic esters were synthesized with good to high yields without a tedious work-up. The process could be done to synthesize the above-mentioned compounds in gram scale. Moreover, oxidative cross-esterification of carboxylic acids with alkyl benzenes was carried out in the above-mentioned DES by the employment of tetrabutylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant at 80?°C. DES/TBAI system was reused up to five consecutive times. Graphic abstract: Iodine-catalyzed C–N and C–O bond formation in choline chloride/urea as a green solvent under the mild reaction conditions. Providing the clean procedure toward synthesis of β-uramino crotonic esters and benzylic esters.[Figure not available: see fulltext.].
Application of acidic ionic liquid to catalyze reaction of cinnamic acid and benzyl alcohol to prepare benzyl cinnamate and method for preparing benzyl cinnamate
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Paragraph 0039-0062, (2021/09/22)
The invention provides an application of an acidic ionic liquid to catalyze the reaction of cinnamic acid and benzyl alcohol to prepare benzyl cinnamate and a method for preparing benzyl cinnamate, and belongs to the technical field of chemical synthesis. The method provided by the invention comprises the following steps of cinnamic acid. The benzyl alcohol and the acidic ionic liquid are mixed to carry out esterification reaction to obtain benzyl cinnamate. By using the acidic ionic liquid as the catalyst, the esterification reaction of cinnamic acid and benzyl alcohol can be effectively catalyzed, the acidic ionic liquid toxicity belongs to low toxic substances, and the pollution to the environment is reduced. Compared with concentrated sulfuric acid, the acidic ionic liquid can greatly reduce the corrosion to equipment. The results show that the yield of benzyl cinnamate provided by the invention is 56.3 ±2.5% - 92.1 ±2.6%.
4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
Gavara, Laurent,Legru, Alice,Verdirosa, Federica,Sevaille, Laurent,Nauton, Lionel,Corsica, Giuseppina,Mercuri, Paola Sandra,Sannio, Filomena,Feller, Georges,Coulon, Rémi,De Luca, Filomena,Cerboni, Giulia,Tanfoni, Silvia,Chelini, Giulia,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois
supporting information, (2021/06/15)
In Gram-negative bacteria, the major mechanism of resistance to β-lactam antibiotics is the production of one or several β-lactamases (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs in an original fashion, and we previously reported its promising potential to yield broad-spectrum inhibitors. However, up to now only moderate antibiotic potentiation could be observed in microbiological assays and further exploration was needed to improve outer membrane penetration. Here, we synthesized and characterized a series of compounds possessing a diversely functionalized alkyl chain at the 4-position of the heterocycle. We found that the presence of a carboxylic group at the extremity of an alkyl chain yielded potent inhibitors of VIM-type enzymes with Ki values in the μM to sub-μM range, and that this alkyl chain had to be longer or equal to a propyl chain. This result confirmed the importance of a carboxylic function on the 4-substituent of 1,2,4-triazole-3-thione heterocycle. As observed in previous series, active compounds also preferentially contained phenyl, 2-hydroxy-5-methoxyphenyl, naphth-2-yl or m-biphenyl at position 5. However, none efficiently inhibited NDM-1 or IMP-1. Microbiological study on VIM-2-producing E. coli strains and on VIM-1/VIM-4-producing multidrug-resistant K. pneumoniae clinical isolates gave promising results, suggesting that the 1,2,4-triazole-3-thione scaffold worth continuing exploration to further improve penetration. Finally, docking experiments were performed to study the binding mode of alkanoic analogues in the active site of VIM-2.