78172-96-0

Usage

InChI:InChI=1/C19H31NO/c1-2-3-4-5-6-7-8-9-13-16-19(21)20-17-18-14-11-10-12-15-18/h10-12,14-15H,2-9,13,16-17H2,1H3,(H,20,21)

Upstream product

• 112-16-3 n-dodecanoyl chloride 
• 100-46-9 benzylamine 
• 1120-16-7 lauric acid amide 
• 108-88-3 toluene 
• 112-54-9 Dodecanal 
• 55-21-0 benzamide 
• 629-25-4 Sodium laurate 
• 3287-99-8 benzylamine hydrochloride 
• 3858-78-4 n-butylamine hydrochloride 
• 143-07-7 lauric acid 
• 106-33-2 ethyl laurate 
• 111-82-0 methyl n-dodecanoate 

Relevant academic research and scientific papers

ALKAMIDE COMPOUNDS AND USES THEREOF

The present disclosure relates to alkamide compounds and compositions for treating allergic diseases, pain, or itch.

Synthesis of: N-acyl amide natural products using a versatile adenylating biocatalyst

Natural products are secondary metabolites produced by many different organisms such as bacteria, fungi and plants. These biologically active molecules have been widely exploited for clinical application. Here we investigate TamA, a key enzyme from the biosynthetic pathway of tambjamine YP1, an acylated bipyrrole that is produced by the marine microorganism Pseudoalteromonas tunicata. TamA is a didomain enzyme composed of a catalytic adenylation (ANL) and an acyl carrier protein (ACP) domain that together control the fatty acid chain length of the YP1. Here we show that the TamA ANL domain alone can be used to generate a range of acyl adenylates that can be captured by a number of amines thus leading to the production of a series of fatty N-acyl amides. We exploit this biocatalytic promiscuity to produce the recently discovered class of N-acyl histidine amide natural products from Legionella pneumophila.

A rare earth/sodium heteroatoms double-metal complex and its preparation and use

The invention discloses a rare earth/sodium heterobimetallic complex as well as a preparation method and application thereof. The molecular formula of the rare earth/sodium heterobimetallic complex is Ln2Na8(OCH2CF3)14(THF)6, wherein Ln represents rare earth metal. The rare earth/sodium heterobimetallic complex disclosed by the invention can be applied to catalysis of the amide exchange reaction to synthesize an amide compound, the reaction conditions are mild, the catalyst dosage is relatively small, and the substrate application range is relatively wide.

An Efficient Heterobimetallic Lanthanide Alkoxide Catalyst for Transamidation of Amides under Solvent-Free Conditions

A practical heterobimetallic lanthanide-catalyzed transamidation of primary, secondary and tertiary amides with aliphatic and aromatic amines has been developed. The methodology was also applied to the weakly reactive thioamides to demonstrate its versatility and wide substrate scope. The heterobimetallic lanthanide catalysts showed high catalytic activity and a wide scope of substrates with good to excellent yields under solvent-free conditions. Efficient activation of the transamidation can be realized by the above complexes acting as cooperative acid–base bifunctional catalysts, which are proposed to be responsible for the higher reactivity in comparison with simple monometallic catalysts. (Figure presented.).

N-Heterocyclic Carbene-Mediated Microfluidic Oxidative Electrosynthesis of Amides from Aldehydes

A flow process for N-Heterocyclic Carbene (NHC)-mediated anodic oxidative amidation of aldehydes is described, employing an undivided microfluidic electrolysis cell to oxidize Breslow intermediates. After electrochemical oxidation, the reaction of the intermediate N-acylated thiazolium cation with primary amines is completed by passage through a heating cell to achieve high conversion in a single pass. The flow mixing regimen circumvented the issue of competing imine formation between the aldehyde and amine substrates, which otherwise prevented formation of the desired product. High yields (71-99%), productivities (up to 2.6 g h-1), and current efficiencies (65-91%) were realized for 19 amides.

Copper-Catalyzed Ligand-Free Amidation of Benzylic Hydrocarbons and Inactive Aliphatic Alkanes

An efficient copper-catalyzed amidation of benzylic hydrocarbons and inactive aliphatic alkanes with simple amides was developed. The protocol proceeded smoothly without any ligand, and a wide range of N-alkylated aromatic and aliphatic amides, sulfonamides, and imides were synthesized in good yields.

Amidation of Carboxylic Acids with Amines by Nb2O5 as a Reusable Lewis Acid Catalyst

Among 28 types of heterogeneous and homogenous catalysts tested, Nb2O5 shows the highest yield for direct amidation of n-dodecanoic acid with a less reactive amine (aniline). The catalytic amidation by Nb2O5 is applicable to a wide range of carboxylic acids and amines with various functional groups, and the catalyst is reusable. A comparison of the results of the catalytic study and an infrared study of the acetic acid adsorbed on the catalyst suggests that activation of the carbonyl group of the carboxylic acid by Lewis acid sites on Nb2O5 is responsible for the high activity of the Nb2O5 catalyst. Kinetic studies show that Lewis acid sites on Nb2O5 are more water-tolerant than conventional Lewis acidic oxides (Al2O3, TiO2). In comparison with the state-of-the-art homogeneous Lewis acid catalyst for amidation (ZrCl4), Nb2O5 undergoes fewer negative effects from basic additives in the solution, which indicates that Nb2O5 is a more base-tolerant Lewis acid catalyst than the homogeneous Lewis acid catalyst.

Synthesis and biological evaluation of a series of fatty acid amides from Echinacea

Abstract Alkylamides are lipophilic constituents of Echinacea and possess numerous biological activities. Although significant effort has been focused on the study of crude Echinacea extracts, very little is known regarding the activities of the individual constituents that make up these herbal treatments. Herein we explore the SAR of simple alkylamides found in Echinacea extracts with respect to their ability to decrease the production of the pro-inflammatory mediator TNF-α. Our results have revealed the key structural requirements for activity and provide lead compounds for further investigation of these poorly understood molecules.

Metallic magnesium: an efficient catalyst toward N-aryl and N-alkyl substituted amides directly from aliphatic carboxylic acids

Abstract An efficient and inexpensive procedure for direct conversion of aliphatic carboxylic acids into amides has been developed using anilines or aliphatic amines and Mg(0) as catalyst in toluene. The amides were obtained by single crystallization in moderate to excellent yields with high purity. Graphical Abstract: [Figure not available: see fulltext.]

Substrate-selective dehydrocondensation at the interface of micelles and emulsions of common surfactants

Scratch the surface: Dehydrocondensations between carboxylates and amines by using an amphiphilic 1,3,5-triazinylammonium-based coupling agent were accelerated by the interfacial effect of micelles and emulsions of common surfactants (see figure). The reaction of carboxylates was promoted by both anionic and nonionic surfactants, and that of amines was promoted by only a nonionic surfactant. High selectivities for more lipophilic substrates were observed in micelles or emulsions. Copyright