1191-16-8Relevant articles and documents
Isoprene related esters, significant components of Pandanus tectorius
Vahirua-Lechat,Menut,Roig,Bessiere,Lamaty
, p. 1277 - 1279 (1996)
Isopentenyl and dimethylallyl acetates and cinnamates have been found in large amounts in an essential oil obtained from the ripe fruit of Pandanus tectorius, their identification has been confirmed by synthesis. This is the first time that these esters, apart from one, have been found in the plant kingdom and, generally speaking, that monoterpene precursors predominate in an essential oil.
A NEW PATHWAY FOR THE SYNTHESIS OF 2,2-DIMETHYL-3,3-DICHLOROCYCLOPROPANECARBOXYLIC ACID
Kryshtal, G. V.,Yanovskaya, L. A.,Volkov, Yu. P.
, p. 620 - 622 (1987)
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Paterno-Buechi reactions of allylic alcohols and acetates with aldehydes: Hydrogen-bond interaction in the excited singlet and triplet states? [2]
Griesbeck,Bondock
, p. 6191 - 6192 (2001)
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Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols
Koszelewski, Dominik,Brodzka, Anna,Madej, Arleta,Trzepizur, Damian,Ostaszewski, Ryszard
, p. 6331 - 6342 (2021/05/06)
Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.
Method for synthesizing acetate perfume
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Paragraph 0070-0073, (2021/01/15)
The invention provides a method for synthesizing acetate by alcohol esterification, which comprises the following steps: by using enol acetate as an esterification reagent, esterifying a primary alcohol, secondary alcohol or tertiary alcohol substrate at high selectivity and high yield under the action of an acidic catalyst to obtain the corresponding acetate products. The method has the main advantages that the synthesis method is novel, enol acetate is used as an esterification reagent, reaction byproducts are micromolecular acetaldehyde or acetone and the like, and the micromolecular compounds do not show acidity and are low in boiling point, so that rearrangement side reaction of an alcohol substrate cannot be caused; and the small molecule byproduct can be conveniently removed from the reaction solution, so that the esterification reaction is promoted to be completely carried out, the reaction stability is good, and the yield is high.
Scalable green approach toward fragrant acetates
Puchl'Ová, Eva,Szolcsányi, Peter
, (2020/08/07)
The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.