115-95-7Relevant academic research and scientific papers
Acylation of linalool in the presence of polymeric pyrrolidinopyridines
Alieva,Truhmanova,Plate
, p. 1226 - 1229 (1996)
The effect of a number of factors on the efficiency of polymers containing immobilized pyrrolidinopyridine groups as polymeric activating reagents for the acylation of weakly reactive sterically hindered alcohols was studied. The conditions of the acylation of linalool with acetic anhydride in the presence of polymeric pyrrolidinopyridines were selected in such a way that the activity of polymeric systems under study was close to that of their low-molecular-weight analog, pyrrolidinopyridine (in a homogeneous medium).
Total partial synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3- acetoxyocta-1,7-diene and (3S, 6S)-(-)-3,7-dimethylocta-1,7-diene-3,6-diol from geraniol
Liu, Zuosheng,Lan, Jiong,Li, Yulin,Xing, Yacheng,Cen, Wen
, p. 324 - 325 (1999)
The synthesis of (3S, 6S)-(+)-3,7-dimethyl-6-hydroxy-3-acetoxyocta-1,7- diene and (3S, 6S)-(-)3,7-dimethylocta-1,7-diene-3,6-diol via the rearrangement of the chiral 2,3-epoxy alcohol, with the system Ph3P, pyridine, I2 and H2O, is described.
Synthesis of dimeric terpenoyl glycoside side chains from cytotoxic saponins
Reicheneder, Sabine,Unverzagt, Carlo
, p. 4353 - 4357 (2004)
A bottleneck in the synthesis of the model compound 1, which bears a dimeric terpenoyl glycoside side chain from cytotoxic saponins, was overcome by the stepwise construction of the terpene part by regioselective acylation of the sugar with a functionalized phosphonate followed by a Horner-Wadsworth-Emmons olefination.
Enantioselective monoterpene alcohol acetylation in Origanum, Mentha and Salvia species
Larkov, Olga,Zaks, Alon,Bar, Einat,Lewinsohn, Efraim,Dudai, Nativ,Mayer, Alfred M.,Ravid, Uzi
, p. 2565 - 2571 (2008)
Selected plants within the Origanum, Mentha and Salvia genera, that contain significant amounts of chiral volatile alcohols and their related acetates, exhibit remarkable enantioselectivity of alcohol acetyl transferase (AAT) activity and particularly can discriminate between linalool enantiomers. Origanum dayi AAT produced almost enantiomerically pure (R)-linalyl acetate by enzymatic acetylation of racemic linalool, whereas the closely related O. majorana AAT produced a mixture of (R)- and (S)-linalyl acetate with a ratio of 6:4. Vmax of O. dayi acetylation activity was 30-fold higher for (R)-linalool, whereas in O. majorana no such differences were found.
Method for synthesizing acetate perfume
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Paragraph 0054-0056, (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.
Preparing method and application of aminopyridine derivative
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Paragraph 0072-0093; 0096; 0097-0100, (2019/07/16)
The invention provides an aminopyridine derivative and a preparing method and application thereof. The structural formula of the aminopyridine derivative is shown in the description, wherein R represents substitute groups and is selected from one or more of alkyl groups of C1-C20, phenyl groups, naphthyls, methoxy groups, benzyloxy groups, fluorine, chlorine, bromine, trifluoromethyl, methoxycarbonyl groups. The preparing method comprises the steps of conducting benzylation on 4-aminopyridine and benzylic halides under action of an alkaline reagent. The aminopyridine derivative is used for catalyzing esterification reaction, and is especially suitable for catalyzing acetic acid esterification reaction with alcohol as the substrate; the reaction speed is high, the yield is high, and the reaction effect and the reaction speed are almost equal to those of 4-dimethylamino pyridine. The aminopyridine derivative has large molecular weight and a high boiling point and accordingly can be separated from primary products and auxiliary products through distillation or rectification and can be reused cyclically ten times or more, the cost of the catalyst is greatly reduced, and the aminopyridine derivative has good industrial application prospects.
Proton-gradient-transfer acid complexes and their catalytic performance for the synthesis of geranyl acetate
Chen, Yongle,Ding, Shiya,Zheng, Wentao,Zhang, Yiyang,Wu, Youting,Hu, Xingbang
, p. 2114 - 2121 (2017/01/16)
Special proton-gradient-transfer acid complexes (PGTACs) in which the bonded protons are not equivalent and have gradients in transfer ability, acidity, and reactivity were reported. The acidity gradient of the protons gave the PGTACs excellent catalytic activity and selectivity in the esterification of terpenols. These PGTACs are “reaction-induced self-separation catalysts” and can be easily reused. The kinetics with PGTACs as catalyst in the esterification of geraniol were also studied for use in engineering design.
Unravelling transition metal-catalyzed terpenic alcohol esterification: A straightforward process for the synthesis of fragrances
Da Silva,Ayala
, p. 3197 - 3207 (2016/05/24)
Iron nitrate is a simple and commercially available Lewis acid and is demonstrated to be able to catalyze β-citronellol esterification with acetic acid, achieving high conversion and ester selectivity (ca. 80 and 70%, respectively), within shorter reaction times than those reported in the literature. To the best of our knowledge, this is the first report of a terpenic alcohol esterification reaction catalyzed by Fe(NO3)3. This process is an attractive alternative to the slow and expensive enzymatic processes commonly used in terpenic alcohol esterification. Moreover, it avoids the undesirable steps of neutralizing the products, which are always required in mineral acid-catalyzed reactions. We have performed a study of the activity of different metal Lewis acid catalysts, and found that their efficiency is directly linked to the ability of the metal cation to generate H+ ions from acetic acid ionization. The measurement of pH as well as the conversions achieved in the reactions allowed us to obtain the following trend: Fe(NO3)3 > Al(NO3)3 > Cu(NO3)2 > Ni(NO3)2 > Zn(NO3)2 > Mn(NO3)2 > Co(NO3)2 > LiNO3. The first three are recognized as stronger Lewis acids and they generate more acidic solutions. When we carried out reactions with different iron salts, it was possible to conclude that the type of anion affects the solubility of the catalyst, as well as the conversion and selectivity of the process. Fe2(SO4)3 and FeSO4 were insoluble and less active. Conversely, though they were equally soluble, Fe(NO3)3 was more selective for the formation of β-citronellyl acetate than FeCl3. We assessed the effects of the main reaction variables such as reactant stoichiometry, temperature, and catalyst concentration. In addition to citronellol, we investigated the efficiency of the iron(iii) catalyst in the solvent free esterification of several terpenic alcohols (geraniol, nerol, linalool, α-terpineol) as well as other carboxylic acids.
Acyl transfer reactions of carbohydrates, alcohols, phenols, thiols and thiophenols under green reaction conditions
Giri, Santosh Kumar,Kartha, K. P. Ravindranathan
, p. 11687 - 11696 (2015/02/19)
Acyl transfer reactions of various carbohydrates, alcohols, phenols, thiols and thiophenols were achieved at room temperature in high yields and catalytic efficiency in the presence of methane sulfonic acid, a green organic acid, under solvent-free conditions over short time periods. The method is mild enough to allow acid labile substituents such as isopropylidene acetals and trityl ethers on the reacting substrates to be left completely unaffected. Esterification of free mono- and dicarboxylic acids such as acetic acid, cinnamic acid, sialic acid and tartaric acid with alcohols such as menthol, ethanol, methanol or propylene glycol has also been achieved efficiently at room temperature. A comparative study of the method with the silica-sulfuric acid is also reported.
