68263-59-2

Upstream product

• 764-85-2 Nonanoyl chloride 
• 100-46-9 benzylamine 
• 112-05-0 nonanoic acid 
• 19211-35-9 N-Methyl-N-nitrosopelargonamide 
• 111-66-0 oct-1-ene 
• 201230-82-2 carbon monoxide 
• 6212-93-7 N-Methylpelargonamide 
• 91083-85-1 N-Butyl-N-nitrosopelargonamide 
• 143-08-8 nonyl alcohol 
• 124-19-6 nonan-1-al 
• 104943-23-9 nonanoic acid N-hydroxysuccinimide ester 
• 5381-93-1 1-hydroxy-1-phenyl-3-butanone 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 

Downstream Products

• 1172110-92-7 N-benzylnonanethioamide 

Relevant academic research and scientific papers

A preparation method of the fatty amide

The invention discloses a preparation method for fatty acyl amide, belonging to the technical field of organic chemical synthesis. The method comprises the following steps: using substituted terminal olefin, carbon monoxide, and aminal or amine as raw materials, then carrying out catalyzation or co-catalyzation with aldehyde via a transition metal catalyst, and carrying out reaction in an organic solvent at 50 to 120 DEG C for 12 to 24 hours under the participation of a ligand or the co-participation of the ligand with an additive; removing the organic solvent when the reaction is completed, and carrying out column chromatography so as to obtain a fatty acyl amide compound. The preparation method for the fatty acyl amide has the following advantages: the raw materials, the catalyst and the additive for the reaction are cheap and easily available; synthetic process is simple; synthetic cost is greatly reduced; reaction conditions are mild; industrialization is easily realized; the raw materials and the catalyst for the reaction are clean and non-toxic and has small pollution to the environment.

Selective Palladium-Catalyzed Aminocarbonylation of Olefins to Branched Amides

A general and efficient protocol for iso-selective aminocarbonylation of olefins with aliphatic amines has been developed for the first time. Key to the success for this process is the use of a specific 2-phosphino-substituted pyrrole ligand in the presence of PdX2(X=halide) as a pre-catalyst. Bulk industrial and functionalized olefins react with various aliphatic amines, including amino-acid derivatives, to give the corresponding branched amides generally in good yields (up to 99 %) and regioselectivities (b/l up to 99:1).

Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis

Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced throughout the one-pot procedure involving multistep catalytic tandem operations. Several novel cocatalytic relay sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.

Palladium-catalyzed hydroaminocarbonylation of alkenes with amines: A strategy to overcome the basicity barrier imparted by aliphatic amines

A novel and efficient palladium-catalyzed hydroaminocarbonylation of alkenes with aminals has been developed under mild reaction conditions, and allows the synthesis of a wide range of N-alkyl linear amides in good yields with high regioselectivity. On the basis of this method, a cooperative catalytic system operating by the synergistic combination of palladium, paraformaldehyde, and acid was established for promoting the hydroaminocarbonylation of alkenes with both aromatic and aliphatic amines, which do not react well under conventional palladium-catalyzed hydroaminocarbonylation. Back to basics: The basicity of aliphatic amines precludes their use in the palladium-catalyzed hydroaminocarbonylation. This issue was overcome by using aminals as surrogates of aliphatic amines. A cooperative catalytic system was discovered to operate by the synergistic combination of palladium, paraformaldehyde, and acid for promotion of the hydroaminocarbonylation of alkenes with both aromatic and aliphatic amines.

Rh(I)-Catalyzed Hydroamidation of Olefins via Selective Activation of N-H Bonds in Aliphatic Amines

Hydroamidation of olefins constitutes an ideal, atom-efficient method to prepare carboxylic amides from easily available olefins, CO, and amines. So far, aliphatic amines are not suitable for these transformations. Here, we present a ligand- and additive-free Rh(I) catalyst as solution to this problem. Various amides are obtained in good yields and excellent regioselectivities. Notably, chemoselective amidation of aliphatic amines takes place in the presence of aromatic amines and alcohols. Mechanistic studies reveal the presence of Rh-acyl species as crucial intermediates for the selectivity and rate-limiting step in the proposed Rh(I)-catalytic cycle. (Chemical Formula Presented).

Polymer-anchored Ru(II) complex as an efficient catalyst for the synthesis of primary amides from nitriles and of secondary amides from alcohols and amines

A polymer-anchored ruthenium(II) catalyst was synthesized and characterized. Its catalytic activity was evaluated for the preparation of primary amides from aqueous hydration of nitriles in neutral condition. A range of nitriles were successfully converted to their corresponding amides in good to excellent yields. The catalyst was also effective in the preparation of secondary amides from the coupling of alcohols and amines. The catalyst can be facilely recovered and reused six times without a significant decrease in its activity.

Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

A wider investigation into the synthesis of secondary amides from primary alcohols using a hydrogen acceptor using commercially available [Ru(p-cymene)Cl2]2 with bis(diphenylphosphino)butane (dppb) as the catalyst. The report looks at over 50 examples with varying functionality and steric bulk, whilst also covering the first reported results using microwave heating to effect the transformation.

Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot

The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.

A copper-catalysed amidation of aldehydes via N-hydroxysuccinimide ester formation

A copper-catalysed oxidative amidation of aldehydes via N-hydroxysuccinimide ester formation is reported. The methodology employed to prepare amides directly from aldehydes has a very wide scope, is high yielding, and does not need dry conditions. This cross-coupling reaction appears to be simple and makes use of cheap, abundant and easily available reagents.

Direct amide synthesis from either alcohols or aldehydes with amines: Activity of Ru(II) hydride and Ru(0) complexes

An in situ generated catalyst from readily available RuH 2(PPh3)4, an N-heterocyclic carbene (NHC) precursor, NaH, and acetonitrile was developed. The catalyst showed high activity for the amide synthesis directly from either alcohols or aldehydes with amines. When a mixture of an alcohol and an aldehyde was reacted with an amine, both of the corresponding amides were obtained with good yields. Homogeneous Ru(0) complexes such as (4-1,5-cyclooctadiene)(6-1,3,5- cyclooctatriene)ruthenium [Ru(cod)(cot)] and Ru3(CO)12 were also active in the amidation of an alcohol or an aldehyde with the help of an in situ generated NHC ligand.