13161-17-6

Upstream product

• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 104-88-1 4-chlorobenzaldehyde 
• 108-94-1 cyclohexanone 
• 10468-40-3 cyclohexanone N-cyclohexylimine 
• 17814-55-0 trichloro<(1-cyclohexenyl)oxy>silane 
• 89-98-5 2-chloro-benzaldehyde 
• 1056477-06-5 2-bromocyclohexanone 
• 873-76-7 para-Chlorobenzyl alcohol 
• 108-93-0 cyclohexanol 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 31020-78-7 2-(4-chlorobenzylidene)cyclohexan-1-one 
• 38968-76-2 2-(4'-chloro)benzoylcyclohexanone 
• 870630-97-0 (2S,1'R)-2-(hydroxy-(p-chlorophenyl)methyl)cyclohexan-1-one 
• 108-94-1 cyclohexanone 
• 13159-12-1 7t-<4-Chlor-phenyl>-hept-6-ensaeure 
• 108-93-0 cyclohexanol 
• 74-11-3 para-chlorobenzoic acid 
• 2702-79-6 2-(4-chloro-benzyl)-cyclohexanone 
• 31021-05-3 (E)-2-(4-chlorobenzylidene)cyclohexanone 

Relevant academic research and scientific papers

The enzymatic asymmetric aldol reaction using acidic protease from Aspergillus usamii

AUAP (acidic protease from Aspergillus usamii) could catalyze the direct aldol reactions between aromatic aldehydes and cyclic ketones in acetonitrile (MeCN) in the presence of water. The enantioselectivities of up to 88% ee and diastereoselectivities of

Biomass waste-derived recyclable heterogeneous catalyst for aqueous aldol reaction and depolymerization of PET waste

In this work, we discuss the valorization of biomass waste-derived orange peel ash (OPA) by exploring its applicability as a heterogeneous catalyst in aqueous aldol reactions and demonstrating its versatility by promoting the methanolysis of poly(ethylene terephthalate) (PET) waste. The catalyst was characterized using Fourier-transform infrared spectroscopy (FT-IR), Brunauer-Emmett-Teller (BET) analysis, X-ray powder diffraction (XRD), X-ray fluorescence (XRF), energy dispersive X-ray (EDX) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and thermal gravimetric analysis (TGA) to decode its chemical composition. The aldol reactions were carried out at ambient temperature in the presence of water as a solvent. PET depolymerization was performed in an autoclave for 1 h using only 6% w/w OPA. The catalyst was recovered and reused in both the reactions for up to four successive cycles with minimal loss in the catalytic activity. The use of OPA as a cost-free, eco-friendly and effective recyclable catalyst enables a greener route for C-C bond formation and PET waste recycling.

A chemo-enzymatic oxidation/aldol sequential process directly converts arylbenzyl alcohols and cyclohexanol into chiral β-hydroxy carbonyls

The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation has great significance, in that it is not only environmentally friendly but also overcomes only a single methodological drawback, either in the chemical or biological process. Herein, through the utilization of the bulky steric hindrance of chiral proline derivatives, an integrated laccase and proline as a chemo-enzymatic co-catalyst system is developed. It enables an efficient oxidation/aldol enantioselective sequential reaction to be accomplished, overcoming the mutual deactivation issue. As we present in this study, this one-pot organic transformation, an initial laccase-mediated oxidation of arylbenzyl alcohols and cyclohexanol to form aldehydes and cyclohexanone, followed by a subsequent proline derivative-catalyzed aldol condensation of the in situ generated intermediates, provides various 1,2-diastereoisomeric chiral β-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.

New Mesoporous silica-supported organocatalysts based on (2S)-(1,2,4-Triazol-3-yl)-Proline: Efficient, reusable, and heterogeneous catalysts for the asymmetric aldol reaction

Novel organocatalytic systems based on the recently developed (S)-proline derivative (2S)-[5-(benzylthio)-4-phenyl-(1,2,4-triazol)-3-yl]-pyrrolidine supported on mesoporous silica were prepared and their efficiency was assessed in the asymmetric aldol rea

A Zn(II)-Coordination Polymer for the Instantaneous Cleavage of Csp3-Csp3 Bond and Simultaneous Reduction of Ketone to Alcohol

Two coordination polymers of Zn(II) and Cu(II) with n-butylmalonic acid have been achieved in this work. The crystallographic structural descriptions along with the sedimentary rock-type microstructural morphology of these two coordination polymers (CPs) have been explored. The reactivity of β-hydroxy ketones with these two CPs has also been investigated. The Zn(II)-CP shows a specific reactivity with β-hydroxy ketone at room temperature and in open air conditions. Through a microcolumn-based filtration technique, the Zn(II)-CP shows the capability to break the Csp3-Csp3 σ bonds of β-hydroxy ketone and simultaneously reduce the associated ketone to alcohol. Such conversion has been progressed without the use of any additional external reducing agent and any chemical workup or column chromatographic purification protocol. Other similar type CPs of Cu(II) and Mn(II) with n-butylmalonic acid completely failed to show similar reactivity with β-hydroxy ketone. On the basis of much experimental evidence, the most possible mechanistic pathway of the reactivity between β-hydroxy ketone and Zn(II)-CP has also been proposed through this work.

Self-assembled Polydiacetylene Nanoribbons for Semi-heterogeneous and Enantioselective Organocatalysis of Aldol Reactions in Water

We report the synthesis, characterization, and supra-molecular assembly of novel diacetylene amphiphilic units bearing a chiral proline-derived head group. In water, these amphiphiles self-assemble into twisted ribbons that are photo-polymerized to afford

Multifunctional phosphoramide-(S)-prolinamide derivatives as efficient organocatalysts in asymmetric aldol and Michael reactions

The synthesis and evaluation of three novel chiral organocatalysts derived from (S)-proline and containing a bis-amidophosphoryl amine fragment are reported. The structure and conformation of the new compounds were determined by NMR spectroscopy and X-ray crystallographic analysis. The present study represents an effort directed to enhance the performance of (S)-proline-derived organocatalysts in asymmetric aldol and Michael reactions by means of increased steric interactions arising from the incorporation of naphthyl moieties in the catalysts. In the event, the stereoselectivity achieved with naphthyl substituents turned out to be rather similar to that obtained with phenyl analogs. Nevertheless, the new organocatalysts exhibited rather good enantio- and diastereoselectivities in aldol reactions with various isatins and aryl carbaldehydes, affording products with up to 94?:?6 diastereomeric ratios and enantiomeric ratios as high as 95?:?5. Furthermore, products obtained from Michael addition reactions exhibited up to 96?:?4 diastereomeric ratios and enantiomeric ratios as high as 98?:?2.

Proline-Glycine Dipeptidic Derivatives of Chiral Phosphoramides as Organocatalysts for the Enantiodivergent Aldol Reaction of Aryl Aldehydes and Isatins with Cyclohexanone in the Presence of Water

The synthesis of several novel organocatalysts derived from (R)- and (S)-proline-glycine dipeptides and incorporating a chiral phosphoramide fragment was accomplished. These chiral compounds catalyze the enantioselective aldol addition reaction of cyclohe

Probing the Synergistic Catalytic Model: A Rationally Designed Urea-Tagged Proline Catalyst for the Direct Asymmetric Aldol Reaction

A urea tag was incorporated at the C-4 position of proline, cis to its COOH group, in order to explore the prospect of a synergistic effect between the two functional groups in the transition state of the enamine route to the asymmetric aldol reaction. Th

Binaphthyl-based chiral bifunctional organocatalysts for water mediated asymmetric List-Lerner-Barbas aldol reactions

Novel binaphthyl-based chiral bifunctional organocatalysts were designed, synthesized and successfully applied to the asymmetric List-Lerner-Barbas aldol reaction in the presence of water. These organocatalysts were found to be effective catalysts for the