1126-18-7Relevant academic research and scientific papers
Alkylation via tris(dialkylamino)sulfonium enolates
Noyori,Nishida,Sakata
, p. 2085 - 2088 (1980)
Tris(dialkylamino)sulfonium enolates generated from tris(diethylamino)sulfonium difluorotrimethylsiliconate and enol silyl ethers are readily alkylated by various alkyl halides under mild conditions.
Cerium(III) Chloride Mediated Michael Addition of RMgX to Nitroenes: a Very Efficient Access to Complex Nitroalkanes
Bartoli, Giuseppe,Bosco, Marcella,Sambri, Letizia,Marcantoni, Enrico
, p. 8651 - 8654 (1994)
Reactions of RMgX-CeCl3 complexes with nitroenes lead to functionalized nitroalkanes in very good yields.
Resolution of Racemic ε-Lactones
Fellous, R.,Lizzani-Cuvelier, L.,Loiseau, M. A.,Sassy, E.
, p. 343 - 346 (1994)
Kinetic resolution of racemic ε-lactones by Pig Liver Esterase give optically active R (+) ε-lactones.When alkyl group is higher than propyl, Horse Liver Esterase leads to the destruction of the opposite enantiomer.Enantiomeric excess is easily evaluated by G.C. on a chiral stationary phase.
One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst
Xue, Weiyang,Gu, Bin,Wu, Huiling,Liu, Mengyang,He, Songbo,Li, Jingmei,Rong, Xin,Sun, Chenglin
, (2021)
2-Alkyl cycloketones are essential chemicals and intermediates for synthetic perfumes and pesticides, which are conventionally produced by multistep process including aldol condensation, separation and hydrogenation. In present work, a batch one-pot cascade approach using aldehydes and cycloketones as the raw materials, and a bifunctional Pd/ZrO2 catalyst was developed for the synthesis of 2-alkyl cycloketones, e.g., cyclohexanone and cycloheptanone. Very high aldehydes (except for paraldehyde with large steric hindrance) conversion and high yields for 2-alkyl cycloketones (e.g., 99 % of conversion for n-butanal and 76 wt.% of yield for 2-butyl cyclohexanone) were obtained at mild temperature of 140 °C. After 10 cycles of reuse, Pd/ZrO2 catalyst showed slight deactivation (ca. 5 % conversion and 10 % yield losses), due to the coke on the catalyst. However, the performance of the catalyst was completely recovered after an oxidative regeneration.
A milk lactone perfume continuous compound into method (by machine translation)
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Paragraph 0045; 0049; 0050, (2019/05/08)
The invention belongs to the technical field of synthetic perfume, and in particular relates to a milk lactone perfume continuous compound into a method, including the role of the alkali under the condition of the aldol reaction, then by hydrogenation reaction, Baeyer - Villiger oxidation, acid continuous hydrolysis, dehydrating and gets milk lactone perfume; the aldol condensation reactions include: part of the as a footing of a cyclohexanone with a alkali mixing, heating processing, the rest [...] butyraldehyde mixture of cyclohexanone with, side drop edge added stirring, and after dropping to continue stirring, thermal insulation reaction-butyraldehyde content to 1% following the end of the reaction; static divider separating the oil, collected and recycled water; collecting oil layer after washing the processing and then transferred to the distillating still distillation recovery excessive cyclohexanone mechanically, the collection of the condensation product of the pan bottom; the invention by adding cyclohexanone in a different way, improving the yield of the aldol condensation reaction; and, of the present invention under the conditions of reaction temperature, can step from an aldol condensation product. (by machine translation)
A ε - decalactone with synthetic perfume production method (by machine translation)
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Paragraph 0073; 0081; 0082; 0083; 0089; 0097; 0098; 0099, (2019/05/28)
The invention belongs to the technical field of spice production, and in particular relates to relates to a ε - decalactone with synthetic perfume production method, including: (1) preparing an aqueous alkali; (2) the preparation of cyclohexanone and butyraldehyde mixture A; (3) the alkali is added to the reactor, the footing cyclohexanone is added to the mix in the reactor; (4) is added to the mixture in the reactor A drop, side drop edge added stirring, after dropping to continue stirring, thermal insulation to react to the detected in-butyraldehyde content of 1% until the following; (5) the step (4) and the product and sequentially through the hydrogenation, separation and purification, oxidation, obtained after the separation and purification of the ε - decalactone synthetic perfume; the invention to butyraldehyde and cyclohexanone as the starting material to aldol condensation reaction, and then after hydrogenation of peracetic acid oxidation ring enlargement reaction synthesis ε - decalactone perfume, to excessive cyclohexanone as the reaction solvent, recovery after mechanically, reduce the reaction solvent separation and purification, and raw materials are easy, the reaction yield is high. (by machine translation)
Synthetic method of epsilon-decalactone perfume
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Paragraph 0062; 0067-0068; 0074; 0079-0081, (2019/05/15)
The invention belongs to the technical field of perfume synthesis, and particularly relates to a synthetic method of epsilon-decalactone perfume. The synthetic method comprises the following steps: (1) mixing an alkaline solution with a part of cyclohexanone, then dropwise adding a mixture of n-butyraldehyde and the rest of cyclohexanone into the mixture, carrying out stirring, and carrying out heat preservation for a reaction; (2) standing the reactants in the step (1), collecting a water layer, collecting an oil layer, and washing the oil layer with water to obtain a condensed product 2-butenyl cyclohexanone crude product; (3) carrying out distilling to recover cyclohexanone to obtain 2-butenyl cyclohexanone; (4) carrying out a hydrogenation reaction; (5) collecting a liquid-phase intermediate product 2-butyl cyclohexanone crude product, and carrying out distilling to obtain 2-butyl cyclohexanone; (6) carrying out an oxidation reaction; and (7) carrying out distilling purification toobtain the epsilon-decalactone perfume product. According to the invention, the cyclohexanone is added into the reaction system in different ways, the excess cyclohexanone is used as a reaction solvent through a stirring dripping technology, and the cyclohexanone is reused after being recycled, so that separation and purification processes of the reaction solvent are reduced, and a high reactionyield is ensured.
Investigating: Saccharomyces cerevisiae alkene reductase OYE 3 by substrate profiling, X-ray crystallography and computational methods
Powell, Robert W.,Buteler, M. Pilar,Lenka, Sunidhi,Crotti, Michele,Santangelo, Sara,Burg, Matthew J.,Bruner, Steven,Brenna, Elisabetta,Roitberg, Adrian E.,Stewart, Jon D.
, p. 5003 - 5016 (2018/10/17)
Saccharomyces cerevisiae OYE 3 shares 80% sequence identity with the well-studied Saccharomyces pastorianus OYE 1; however, wild-type OYE 3 shows different stereoselectivities toward some alkene substrates. Site-saturation mutagenesis of Trp 116 in OYE 3 followed by substrate profiling showed that the mutations had relatively little effect, opposite to that observed previously for OYE 1. The X-ray crystal structures of unliganded and phenol-bound OYE 3 were solved to 1.8 and 1.9 ? resolution, respectively. Both structures were nearly identical to that of OYE 1, with only a single amino acid difference in the active site region (Ser 296 versus Phe 296, part of loop 6). Despite their essentially identical static X-ray structures, molecular dynamics (MD) simulations revealed that loop 6 conformations differed significantly in solution between OYE 3 and OYE 1. In OYE 3, loop 6 remained nearly as open as observed in the crystal structure; by contrast, loop 6 closed over the active site of OYE 1 by ca. 4 ?. Loop closure likely generates a greater number of active site protein contacts for substrate bound to OYE 1 as compared to OYE 3. These differences provide an explanation for the differing stereoselectivities of OYE 3 and OYE 1, despite their nearly identical X-ray crystal structures.
Direct α-alkylation of ketones with alcohols in water
Xu, Guoqiang,Li, Qiong,Feng, Jiange,Liu, Qiang,Zhang, Zuojun,Wang, Xicheng,Zhang, Xiaoyun,Mu, Xindong
, p. 105 - 109 (2014/03/21)
The direct α-alkylation of ketones with alcohols has emerged as a new green protocol to construct C-C bonds with H2O as the sole byproduct. In this work, a very simple and convenient Pd/C catalytic system for the direct a-alkylation of ketones with primary alcohols in pure water is developed. Based on this catalytic system, aqueous mixtures of dilute acetone, 1-butanol, and ethanol (mimicking ABE fermentation products) can be directly transformed into C5-C11 or longer-chain ketones and alcohols, which are precursors to fuels.
Pichia stipitis OYE 2.6 variants with improved catalytic efficiencies from site-saturation mutagenesis libraries
Patterson-Orazem, Athéna,Sullivan, Bradford,Stewart, Jon D.
, p. 5628 - 5632 (2015/01/09)
An earlier directed evolution project using alkene reductase OYE 2.6 from Pichia stipitis yielded 13 active site variants with improved properties toward three homologous Baylis-Hillman adducts. Here, we probed the generality of these improvements by testing the wild-type and all 13 variants against a panel of 16 structurally-diverse electron-deficient alkenes. Several substrates were sterically demanding, and as hoped, creating additional active site volume yielded better conversions for these alkenes. The most impressive improvement was found for 2-butylidenecyclohexanone. The wild-type provided less than 20% conversion after 24 h; a triple mutant afforded more than 60% conversion in the same time period. Moreover, even wild-type OYE 2.6 can reduce cyclohexenones with very bulky 4-substituents efficiently.
