70659-87-9

Usage

InChI:InChI=1/C15H23NO/c1-2-3-4-5-9-12-15(17)16-13-14-10-7-6-8-11-14/h6-8,10-11H,2-5,9,12-13H2,1H3,(H,16,17)

Upstream product

• 124-07-2 Octanoic acid 
• 100-46-9 benzylamine 
• 106-32-1 octanoic acid ethyl ester 
• 10276-85-4 benzyl caprylate 
• 629-05-0 n-octyne 
• 111-87-5 octanol 
• 67-56-1 methanol 
• 1119-57-9 N-methyloctanoylamide 
• 15567-46-1 N-methyl-N-nitrosooctanoylamide 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 7608-06-2 n-heptylzinc bromide 
• 5457-78-3 phenyl octanoate 
• 124-13-0 Octanal 
• 7530-92-9 octanethioic S-acid 

Downstream Products

• 161643-01-2 N‐benzyloctan‐1‐imine 

Relevant academic research and scientific papers

Half-Sandwich Ruthenium Complexes Bearing Hemilabile κ2-(C,S)?Thioether-Functionalized NHC Ligands: Application to Amide Synthesis from Alcohol and Amine

Amide synthesis is one of the most crucial transformations in chemistry and biology. Among various catalytic systems, N-heterocyclic carbene (NHC)-based ruthenium (Ru) catalyst systems have been proven to be active for direct synthesis of amides by sustainable acceptorless dehydrogenative Coupling of primary alcohols with amines. Most often, these catalytic systems usually use monodentate NHC and thus require an additional ligand to obtain high reactivity and selectivity. In this work, a series of cationic Ru(II)(η6-p-cymene) complexes with thioether-functionalized N-heterocyclic carbene ligands (imidazole and benzimidazole-based) have been prepared and fully characterized. These complexes have then been used in the amidation reaction and the most promising one (i. e. 3 c) has been applied on a large range of substrates. High conversions albeit with moderate yields have generally been obtained.

Fluorinated solvent-assisted photocatalytic aerobic oxidative amidation of alcoholsviavisible-light-mediated HKUST-1/Cs-POMoW catalysis

Considering the irreplaceable importance of photocatalytic functionalization reactions and the widespread attention paid to the use of metal-organic frameworks, especially their modified variants, for this purpose in recent years, different types of HKUST-1/POMoW composites were prepared through the immobilization of a series of Keggin-type polyoxometalates (POMs; POW = H3PW12O40, POMo = H3PMo12O40, and POMoW = H3PMo6W6O40) on HKUST-1 as a metal-organic framework (HKUST-1; Cu3(1,3,5-benzenetricarboxilicacid)2). Then, to produce HKUST-1/Cs-POM, the substitution of H+cations with Cs+ones as counter cations was carried out. The prepared composites were fully characterized with the PXRD (powder X-ray diffraction), FT-IR (Fourier transform infrared spectroscopy), BET and BJH (sorption of N2), TGA (thermo-gravimetric analysis), SEM (scanning electron microscopy), EDX (energy dispersive X-ray), TEM (transmission electron microscopy), UV-vis DRS (diffuse reflectance UV-vis spectroscopy), photoluminescence (PL) spectroscopy and ICP-AES (inductively coupled plasma atomic emission spectroscopy) techniques. The great importance?of the amide functional group and the attractiveness of photocatalytic oxidative functionalization?reactions led us to study the formation of this functional group using the prepared catalytic system in line with our previous research in this field. The HKUST-1/Cs-POMoW composite showed a raised photocatalytic performance compared to the discrete components, HKUST-1 and Cs-POMs, in aerobic oxidative amidation of alcohols under illumination with visible light, owing to the presence of catalytically active Cs-POMs deposited on the MOF particles. Besides, the combination of composite components mitigated the recombination rate of the electron-hole pairs, raising its photocatalytic activity. The attractiveness of fluorine solvents for oxidation reactions has led to the study of their role in the efficiency of oxidative amidation of alcohols and their significant effect on the efficiency of the process has been confirmed. The Cu-MOF/POM catalyst showed excellent stability during the reaction, and no significant decrease in its ability was observed during five consecutive cycles.

Synthesis and biological screening of a library of macamides as TNF-α inhibitors

Thirty-five macamide analogues were synthesised by modifying the initial molecular structure. The resulting structures were confirmed using NMR and MS. Cytotoxicity and the anti-inflammatory activity of these synthetic macamides were evaluated in the THP-1 cell line. Preliminary biological evaluation indicated that most of these synthetic macamides did not present cytotoxicity (MTT assay) in the tested cell line with respect to the control (actinomycin D). Regarding the anti-inflammatory activity, several analogues had a greater potential for inhibition of TNF-α than natural macamides. Synthetic macamide 4a was the most active (IC50 = 0.009 ± 0.001 μM) compared to the C87 (control). Through looking at the link between the chemical structure and the activity, our study proves that changes made to natural macamides at the level of the alkyl chain, the benzyl position, the amide bond, and the addition of two methyl groups to the aromatic ring (meta position) lead us to obtaining new macamides with greater anti-inflammatory activity. This journal is

Direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2

This paper described a mild and efficient direct amidation of non-activated carboxylic acid and amine derivatives catalyzed by TiCp2Cl2. Arylacetic acid derivatives reacted with different amines to afford the corresponding amides in good to excellent yield except of aniline. Aryl formic acids failed to react with aniline but smoothly reacted with aliphatic amines and benzylamine in moderate to good yield, fatty acids reacting with benzyl and aliphatic amines give amides in good to excellent yield. Chiral amino acids derivatives were transformed into amides without racemization in moderate yield. The possible mechanism of direct amidation catalyzed by TiCp2Cl2 was discussed. This catalytic method is very suitable for the amidation of low sterically hindered arylacetic acid, fatty acids with different low sterically hindered amines except aniline, as well as the amidation of aryl formic acid with benzyl and aliphatic amines.

Total syntheses of (?)-emestrin H and (?)-asteroxepin

First total syntheses of (?)-emestrin H and (?)-asteroxepin are described. To find the appropriate protecting group on the amide nitrogen of the diketopiperazine core, we conducted model studies using a simple diketopiperazine derivative. As a result, allyloxymethyl (Allom) group was the most suitable protecting group, which tolerated Nicolaou's sulfenylation conditions, and was easily cleavable under the mild conditions using Pd(PPh3)4 and N,N-dimethylbarbituric acid leaving methylthioethers intact. The general utility of Allom group for protection of amides was studied using simple substrates. Finally, the effectiveness of Allom group was proved by the accomplishment of the first total synthesis of (?)-emestrin H. Allom group was robust enough during installation of two methylthioethers to the diketopiperazine core and easily removed at the final step. The first total synthesis of (?)-asteroxepin was also completed by acylation of (?)-emestrin H.

Tert -Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions

A mild and efficient method is demonstrated for the transamidation of secondary amides with various amines including primary, secondary, cyclic and acyclic amines in the presence of tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the transamidation products in good to excellent yields at room temperature. Moreover, the developed methodology does not require any catalyst or additives.

A Diaminopropane Diolefin Ru(0) Complex Catalyzes Hydrogenation and Dehydrogenation Reactions

New ruthenium (0) complexes with a cooperative diolefin diaminopropane (DAP) or the dehydrogenated iminopropenamide ligand (IPA) were synthesized for comparison with their diaminoethane (DAE)/ diazadiene (DAD) ruthenium analogues. These DAP/IPA complexes are efficient catalysts in dehydrogenation reactions of alkaline aqueous methanol which proceeds under mild conditions (T=70 °C) and of higher alcohols, forming the corresponding carbonate and carboxylates, respectively. The scope of the reaction includes an example of a 1,2-diol as model for biomass derived alcohols. Their catalytic applications are extended to the atom-efficient dehydrogenative coupling of alcohols and amines to amides. The reaction proceeds without any additives and is applicable to the synthesis of formamides from methanol. Moreover, DAP/IPA complexes catalyze the hydrogenation of a series of esters, lactone, ketone, activated olefin, aldehyde and imine substrates. The diaminopropane Ru catalyst exhibits higher activity compared to the dehydrogenated β-ketiminate (IPA) and previously studied DAD/DAE based catalysts. We present studies on their stoichiometric reactivity with relevance to their possible catalytic mechanisms and the isolation and full characterization of key reaction intermediates.

Lipase-catalyzed amidation of carboxylic acid and amines

The amidation reaction is of a very particular interest, especially in the pharmaceutical industry and always requires the activation of the acid with a large excess of reactants. Therefore, a large amount of waste is generated. In order to reduce the environmental impact of such reaction, we have developed enzymatic amidation conditions which are compatible with a wide range of amines and acids, in particular with the biologically relevant lipoic acid. Water is the only by-product generated during this reaction thus a very high atom economy is obtained. In addition, we have shown that the lipase can be recovered and reused several times without a significant loss of activity.

Amide Synthesis via Aminolysis of Ester or Acid with an Intracellular Lipase

A unique lipase (SpL) from Sphingomonas sp. HXN-200 was discovered as the first intracellular enzyme for the aminolysis of ester or acid to produce amide. Reactions of a series of esters and amines with SpL gave the corresponding amides 3a-g in high yield with high activity. SpL also showed high enantioselectivity and high activity for enantioselective ester aminolysis, producing amides (R)-3h-j in high ee from the corresponding racemic ester or amine. Moreover, SpL was found to be highly active for the aminolysis of carboxylic acid, which was generally considered infeasible with the known aminolysis enzymes. The aminolysis of several carboxylic acids afforded the corresponding amides 3a, 3d, 3k, 3l, and 3n in good yield. The intracellular SpL was expressed in Escherichia coli cells to give an efficient whole-cell biocatalyst for amide synthesis. Remarkably, high catalytic activity was observed in the presence of water at 2-4% (v/v) for free enzyme and 16% (v/v) for whole cells, respectively. Accordingly, E. coli (SpL) wet cells were used as easily available and practical catalysts for the aminolysis of ester or acid, producing a group of useful and valuable amides in high concentration (up to 103 mM) and high yield. The newly discovered intracellular SpL with unique properties is a promising catalyst for green and efficient synthesis of amides.

Synthesis of Aliphatic Carboxamides Mediated by Nickel NN2-Pincer Complexes and Adaptation to Carbon-Isotope Labeling

The development of a nickel-mediated aminocarbonylation utilizing NN2-pincer Ni-complexes, alkylzinc reagents, stoichiometric carbon monoxide and amines is described for the first time, which can be adapted to late-stage carbon-isotope labeling. This work expands the scope of the highly established palladium-promoted version of the reaction, by allowing carbon-sp3 fragments to take part in the three-component reaction. Finally, the results obtained show a remarkable effect of the pincer ligand for the reductive elimination step with the amine, which is followed by 13C NMR spectroscopy studies.