20172-41-2

Upstream product

• 2016-57-1 1-aminodecane 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 53044-19-2 N-decylbenzamide 

Downstream Products

• 1558953-49-3 1-(N-(N^α,N^ε-di-Boc-Lys)-N-decylamino)methylbenzene 
• 5461-36-9 N-decyl-1-aminomethylbenzene hydrochloride 
• 1687-67-8 N-benzyl-decan-1-amine 
• 1342283-69-5 N-decyl-N-benzyl-3-(3,4 dihydroxyphenyl)propanamide 

Relevant academic research and scientific papers

Reduction of secondary carboxamides to imines

This article reports in detail on the discovery that zirconium(IV) salts of secondary amides and lactams are transformed by Cp2ZrHCl to N-substituted imines in one step. The method represents the first controlled reduction of amides and lactams to the corresponding imines, a transformation that is otherwise very difficult to achieve because imines are reduced more rapidly than carboxamides by most metal hydride reagents. No products of reductive cleavage of the carboxamides are observed. Efforts to replace 2 mol equiv of Cp2ZrHCl with simpler, less costly alternatives led to the finding that a diisobutylaluminum enolate can be substituted for the initial zirconium enolate. Such aluminum amides are smoothly reduced to the corresponding imine using Cp2ZrHCl in good yield. Moreover, aluminum amides are also reduced to imines using either lowvalent titanium species or triethylsilane. In these alternative procedures, use of Cp2ZrHCl is eliminated altogether in the title transformation.

REDUCTIVE DEOXYGENATION BY Cp2ZrHCl: SELECTIVE FORMATION OF IMINES VIA ZIRCONATION/HYDROZIRCONATION OF AMIDES

A general new process is described by which zirconium(IV) salts of secondary amides and lactams are transformed by Cp2ZrHCl directly into N-substituted imines in one step.

Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile

Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.

Aryl-alkyl-lysines: Membrane-Active Fungicides That Act against Biofilms of Candida albicans

Mortality due to pathogenic fungi has been exacerbated by the rapid development of resistance to frontline antifungal drugs. Fungicidal compounds with novel mechanisms of action are urgently needed. Aryl-alkyl-lysines, which are membrane-active small molecules, were earlier shown to be broad-spectrum antibacterial agents with potency in vitro and in vivo. Herein, we report the antifungal properties of aryl-alkyl-lysines. After identifying the most active compound (NCK-10), we tested its activity against a panel of clinically relevant pathogenic fungi and examined NCK-10's effect against immature and mature biofilms of Candida albicans. NCK-10 was capable of inhibiting the growth of various species of fungi (including Candida spp., Cryptococcus spp., and Aspergillus fumigatus) at concentrations similar to those of antifungal drugs used clinically. It was observed that polarization and permeability of the fungal cell membrane were compromised upon addition of NCK-10, indicating its mechanism is disruption of the fungal cell membrane. In addition to interfering with the growth of planktonic fungi, NCK-10 demonstrated the ability to both inhibit biofilm formation and reduce the metabolic activity of cells in C. albicans biofilm. Additionally, our compound was capable of crossing the blood-brain barrier in an in vitro model, expanding the potential antifungal applications for NCK-10. Overall, aryl-alkyl-lysines were found to be excellent compounds that warrant further investigation as novel antifungal agents.

Heterogeneous copper-catalyzed coupling of amines: a possible way for the preparation of imines

Copper(II) on 4-? molecular sieves is an efficient catalyst for the preparation of imines from benzylamines under simple reaction conditions. No oxidative atmosphere or oxidizing agents are required. Preparative experiments showed that no aldehyde intermediate can be detected even under ambient atmospheric conditions. Graphical abstract: [Figure not available: see fulltext.]

Small molecular antibacterial peptoid mimics: The simpler the better!

The emergence of multidrug resistant bacteria compounded by the depleting arsenal of antibiotics has accelerated efforts toward development of antibiotics with novel mechanisms of action. In this report, we present a series of small molecular antibacterial peptoid mimics which exhibit high in vitro potency against a variety of Gram-positive and Gram-negative bacteria, including drug-resistant species such as methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium. The highlight of these compounds is their superior activity against the major nosocomial pathogen Pseudomonas aeruginosa. Nontoxic toward mammalian cells, these rapidly bactericidal compounds primarily act by permeabilization and depolarization of bacterial membrane. Synthetically simple and selectively antibacterial, these compounds can be developed into a newer class of therapeutic agents against multidrug resistant bacterial species.

NaOH-catalyzed imine synthesis: Aerobic oxidative coupling of alcohols and amines

The convenient transition-metal-free synthesis of imines through oxidative coupling of alcohols and amines is reported. The reaction is catalyzed by NaOH (10 mol-%) and is performed with air as an oxidant in the absence of any co-solvent. The convenient transition-metal-free synthesis of imines through oxidative coupling of alcohols and amines is reported. The reaction is catalyzed by NaOH (10 mol-%) and is performed with air as an oxidant in the absence of any co-solvent. Copyright

Novel caffeic acid amide antioxidants: Synthesis, radical scavenging activity and performance under storage and frying conditions

Twelve novel dihydro-caffeic acid amides were synthesised in good yields and fully characterised by 1H NMR, 13C NMR, and MS. Their radical scavenging activities were assessed by DPPH assay. Additionally, their abilities to protect polyunsaturated oils under accelerated storage and frying conditions were evaluated. All the new compounds possessed significantly higher radical scavenging activities than α-tocopherol and butylated hydroxytoluene (BHT). The radical scavenging activity of N-decyl-N-(3,5- dimethoxy-4-hydroxybenzyl)-3-(3,4-dihydroxyphenyl) propanamide was 1.7 and 4 times higher than α-tocopherol and BHT, respectively. At the end of the storage period, the respective amounts of hydroperoxides in canola oil triacylglycerols (CTAG) fortified with α-tocopherol and BHT was 6.1 and 1.4 times higher, respectively, than CTAG containing the amide. The frying test showed that CTAG containing N-decyl-N-benzyl-3-(3,4-dihydroxybenzyl) propanamide was 1.3, 1.4, and 1.6 times more stable compared to oil fortified with dihydro-caffeic acid, α-tocopherol and BHT, respectively, as assessed by the amounts of the total polar compounds. Moreover, these compounds were remarkably thermally stable, making them suitable for frying applications.

Using quenching kinetics and thermodynamics of amino-fluorophores as empirical tools for predicting boronic acid sensors suitable for use in physiological conditions

A series of water-soluble 1-amino-naphthalenes and 2-amino-fluorenes are prepared. These serve as model fluorophores for measuring the thermodynamics and kinetics of fluorescence quenching with phenylboronic acids and aliphatic amines. Steady-state and ti

Aqueous solutions of geminal alkylammonium surfactants as a medium for reactions of long-chain amines

The formation of surfactant-hydrophobic amine mixed aggregates reduces the pK a of long-chain amines by 1-1.5 units compared with those in molecular solutions and is an important factor responsible for the high catalytic effect of the system in