103-48-0Relevant academic research and scientific papers
Odor-structure relationships using fluorine as a probe
Michel, Dominique,Schlosser, Manfred
, p. 4253 - 4260 (2000)
Eight ethers, nine esters and one ketone were submitted to a systematic structural variation by replacing a hydrogen atom in the vicinity of the oxofunction by fluorine and methyl. As long as steric factors dominate, a fluorine substituent alters the olfactory properties of the parent compound much less than a methyl substituent does. However, if it occupies a position adjacent to a carbonyl group, the halogen may more profoundly affect the odor perception, presumably as a consequence of conformational changes. (C) 2000 Elsevier Science Ltd.
Direct formation of esters and amides from carboxylic acids using diethyl chlorophosphate in pyridine
McNulty, James,Krishnamoorthy, Venkatesan,Robertson, Al
, p. 6344 - 6347 (2008)
An efficient method involving pyridine activation of the carboxylate-phosphate anhydride pathway is described resulting in a direct synthesis of esters from carboxylic acids and alcohols, as well as in the formation of useful amide and peptide derivatives. The reaction proceeds with retention of configuration with both chiral secondary alcohols and α-amino acid derivatives. Ester and amide products can be isolated directly in high yield due to the water soluble nature of the side products.
Synthesis method of p-hydroxyphenethyl alcohol
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Paragraph 0051; 0052; 0053, (2019/09/17)
The invention discloses a method for synthesizing p-hydroxyphenethyl alcohol from phenethyl alcohol as a raw material. The method comprises the steps as follows: firstly, phenethyl alcohol and acid anhydride are subjected to an esterification reaction to obtain phenethyl alcohol ester; then, phenethyl alcohol ester and acid anhydride are subjected to an electrophilic substitution reaction under the action of a catalyst and a catalyst promoter to obtain 4-acryl phenethyl alcohol ester; next, 4-acryl phenethyl alcohol ester and hydrogen peroxide are subjected to a Baeyer-Villiger oxidation reaction under the action of organic acid and an oxidation catalyst to obtain 4-acyloxy phenethyl alcohol ester; finally, the 4-acyloxy phenethyl alcohol ester is subjected to a hydrolysis reaction in alkaline water to obtain p-hydroxyphenethyl alcohol. The process for synthesizing p-hydroxyphenethyl alcohol has the advantages that raw materials are widely sourced, the yield is high, the process is concise, few three wastes are produced and industrialization is easy to realize.
Lewis Acid Catalyzed Synthesis of α-Trifluoromethyl Esters and Lactones by Electrophilic Trifluoromethylation
Katayev, Dmitry,Matou?ek, Václav,Koller, Raffael,Togni, Antonio
supporting information, p. 5898 - 5901 (2015/12/11)
An electrophilic trifluoromethylation of ketene silyl acetals (KSAs) by hypervalent iodine reagents 1 and 2 has been developed. The reaction proceeds under very mild conditions in the presence of a catalytic amount of trimethylsilyl bis(trifluoromethanesulfonyl)imide (up to 2.5 mol %) as a Lewis acid providing a direct access to a variety of secondary, tertiary, and quaternary α-trifluoromethyl esters and lactones in high yield (up to 98%).
Expanding ester biosynthesis in Escherichia coli
Rodriguez, Gabriel M,Tashiro, Yohei,Atsumi, Shota
, p. 259 - 265 (2014/04/03)
To expand the capabilities of whole-cell biocatalysis, we have engineered Escherichia coli to produce various esters. The alcohol O-acyltransferase (ATF) class of enzyme uses acyl-CoA units for ester formation. The release of free CoA upon esterification with an alcohol provides the free energy to facilitate ester formation. The diversity of CoA molecules found in nature in combination with various alcohol biosynthetic pathways allows for the biosynthesis of a multitude of esters. Small to medium volatile esters have extensive applications in the flavor, fragrance, cosmetic, solvent, paint and coating industries. The present work enables the production of these compounds by designing several ester pathways in E. coli. The engineered pathways generated acetate esters of ethyl, propyl, isobutyl, 2-methyl-1-butyl, 3-methyl-1-butyl and 2-phenylethyl alcohols. In particular, we achieved high-level production of isobutyl acetate from glucose (17.2 g l -1). This strategy was expanded to realize pathways for tetradecyl acetate and several isobutyrate esters.
Pentafluorophenylammonium triflate as a mild and new organocatalyst for acylation of alcohols, phenols, and amines under solvent-free condition
Khaksar, Samad,Zakeri, Hasan
, p. 576 - 579,4 (2020/08/31)
A simple, inexpensive, environmentally friendly and efficient route for the acylation of a number of alcohols, phenols and amines using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. PFPAT organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from the reaction mixtures.
The phosphate-carboxylate mixed-anhydride method: A mild, efficient process for ester and amide bond construction
McNulty, James,Vemula, Ramesh,Krishnamoorthy, Venkatesan,Robertson, Al
experimental part, p. 5415 - 5421 (2012/09/08)
A highly efficient carboxylate-phosphate anhydride pathway is described for the direct, economical synthesis of esters and amides from carboxylic acids and alcohols or amines. The reaction proceeds with retention of configuration with both chiral secondary alcohols and α-amino acid derivatives allowing access to useful chiral auxiliaries, ligands, and organocatalysts. Ester and amide products can be isolated directly in high yield due to the water soluble nature of the side products.
Organocatalytic chemoselective monoacylation of 1,n-linear diols
Yoshida, Keisuke,Furuta, Takumi,Kawabata, Takeo
supporting information; experimental part, p. 4888 - 4892 (2011/06/22)
Matters of length: Exclusive or predominant monoacylation of 1,n-linear diols took place in the presence of 1 when the chain length of linear diols was equal to or shorter than five carbon atoms. The chemoselectivity of acylation between 1,5-pentanediol (n=5) and 1,6-hexanediol (n=6) was 5.2, and that between 1,5-pentanediol and its monoacylate was 113. Copyright
Transesterification catalyzed by iron(III) β-diketonate species
Weng, Shiue-Shien,Ke, Chih-Shueh,Chen, Fong-Kuang,Lyu, You-Fu,Lin, Guan-Ying
supporting information; experimental part, p. 1640 - 1648 (2011/04/17)
A practical and clean protocol for transesterification catalyzed by a 5 mol % cheap, non-toxic and moisture stable Fe(acac)3 or other iron(III) β-diketonate species in solvent, such as heptane under azeotropic condition is developed. A remarkable rate enhancement was observed upon the addition of 5 mol % of an inorganic base, such as Na2CO3, which suggests that faster formation of a dimeric μ-alkoxy-bridged iron(III) species under alkaline conditions facilitates catalytic turnover. This system provides smooth transesterification over a wide range of structurally diverse esters and alcohols without disturbing functional groups. In addition, the use of iron β-diketonate complexes as catalysts is more environmentally friendly, safer, and economical than other transition-metal catalysts. Preliminary mechanistic studies indicate that the active catalyst is likely a dimeric μ-alkoxy-bridged iron(III) species, as determined by X-ray crystallography of [Fe(dbm)2(O-n-Bu)]2 derived from the alcoholysis of Fe(dbm)3 under alkaline conditions.
Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast
Kuninobu, Yoichiro,Kawata, Atsushi,Noborio, Taihei,Yamamoto, Syun-Ichi,Matsuki, Takashi,Takata, Kazumi,Takai, Kazuhiko
experimental part, p. 941 - 945 (2010/07/07)
Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.
