70419-10-2

Usage

Chemical Properties

brown liquid

Upstream product

• 928-68-7 6-methylheptan-2-one 
• 543-82-8 1,5-dimethylhexylamine 
• 1222802-05-2 N-octanoyl-L-alanine 2,2,2-trifluoroethyl ester 
• 1100753-75-0 N-octanoylglycine 2,2,2-trifluoroethyl ester 
• 143-07-7 lauric acid 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 70419-11-3 (R)-6-methylheptan-2-amine 
• 540-69-2 ammonium formate 
• 3852-09-3 methyl 3-methoxypropionate 
• 815-57-6 3-Methyl-2,4-pentanedione 
• 1384127-07-4 N-octanoyl dimethyl glycine trifluoroethyl ester 

Downstream Products

• 30121-77-8 N-(4-{[(E)-1,5-Dimethyl-hexylimino]-methyl}-phenyl)-acetamide 
• 30121-68-7 (1,5-Dimethyl-hexyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 30121-75-6 [1-(2,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-(1,5-dimethyl-hexyl)-amine 
• 1244047-15-1 N-((S)-1-((S)-6-methylheptan-2-ylcarbamoyl)ethyl)octanamide 
• 1322805-10-6 (R)-3-methoxy-N-(6-methylheptan-2-yl) propanamide 

Relevant academic research and scientific papers

Ruthenium Catalyzed Direct Asymmetric Reductive Amination of Simple Aliphatic Ketones Using Ammonium Iodide and Hydrogen

The direct conversion of ketones into chiral primary amines is a key transformation in chemistry. Here, we present a ruthenium catalyzed asymmetric reductive amination (ARA) of purely aliphatic ketones with good yields and moderate enantioselectivity: up to 99 percent yield and 74 percent ee. The strategy involves [Ru(PPh3)3H(CO)Cl] in combination with the ligand (S,S)-f-binaphane as the catalyst, NH4I as the amine source and H2 as the reductant. This is a straightforward and user-friendly process to access industrially relevant chiral aliphatic primary amines. Although the enantioselectivity with this approach is only moderate, to the extent of our knowledge, the maximum ee of 74 percent achieved with this system is the highest reported till now apart from enzyme catalysis for the direct transformation of ketones into chiral aliphatic primary amines.

Separate Sets of Mutations Enhance Activity and Substrate Scope of Amine Dehydrogenase

Mutations were introduced into the leucine amine dehydrogenase (L-AmDH) derived from G. stearothermophilus leucine dehydrogenase (LeuDH) with the goals of increased activity and expanded substrate acceptance. A triple variant (L-AmDH-TV) including D32A, F101S, and C290V showed an average of 2.5-fold higher activity toward aliphatic ketones and an 8.0 °C increase in melting temperature. L-AmDH-TV did not show significant changes in relative activity for different substrates. In contrast, L39A, L39G, A112G, and T133G in varied combinations added to L-AmDH-TV changed the shape of the substrate binding pocket. L-AmDH-TV was not active on ketones larger than 2-hexanone. L39A and L39G enabled activity for straight-chain ketones as large as 2-decanone and in combination with A112G enabled activity toward longer branched ketones including 5-methyl-2-octanone.

Reusable Nickel Nanoparticles-Catalyzed Reductive Amination for Selective Synthesis of Primary Amines

The preparation of nickel nanoparticles as efficient reductive amination catalysts by pyrolysis of in situ generated Ni-tartaric acid complex on silica is presented. The resulting stable and reusable Ni-nanocatalyst enables the synthesis of functionalized and structurally diverse primary benzylic, heterocyclic and aliphatic amines starting from inexpensive and readily available carbonyl compounds and ammonia in presence of molecular hydrogen. Applying this Ni-based amination protocol, -NH2 moiety can be introduced in structurally complex compounds, for example, steroid derivatives and pharmaceuticals.

Reshaping the Active Pocket of Amine Dehydrogenases for Asymmetric Synthesis of Bulky Aliphatic Amines

The asymmetric reductive amination of ketones with ammonia using engineered amine dehydrogenases (AmDHs) is a particularly attractive and environmentally friendly method for the synthesis of chiral amines. However, one major challenge for these engineered AmDHs is their limited range of accepted substrates. Herein, several engineered AmDHs were developed through the evolution of naturally occurring leucine dehydrogenases, which displayed good amination activity toward aliphatic ketones but restricted catalytic scope for short-chain substrates. Computational analysis helped identify two residues, located at the distal end of the substrate-binding cavity, that generate steric hindrance and prevent the binding of bulky aliphatic ketones. By fine-tuning these two key hotspots, the resulting AmDH mutants are able to accept previously inaccessible bulky substrates. More importantly, the mutations were also proved applicable for expanding the substrate scope of other homologous AmDHs with sequence identities as low as 70%, indicating a broad effect on the development of AmDHs and the synthesis of structurally diverse chiral amines.

Asymmetric catalysis of the carbonyl-amine condensation: Kinetic resolution of primary amines

A Br?nsted acid catalyzed kinetic resolution of primary amines is described that is based on the condensation between an amine and a carbonyl compound. 1,3-Diketones react with racemic α-branched amines to furnish the corresponding enantioenriched enaminone and recovered starting material. Good to excellent enantioselectivity was observed with both aromatic and aliphatic primary amines. This process represents the first small-molecule catalyzed kinetic resolution of aliphatic amines.

N-octanoyldimethylglycine trifluoroethyl ester, an acyl donor leading to highly enantioselective protease-catalysed kinetic resolution of amines

The use of N-octanoyldimethylglycine trifluoroethyl ester as acyl donor in the kinetic resolution of aliphatic amines catalysed by proteases led to enantiomeric ratios >200 in most cases. The resolutions mediated by Protex 6L were shown to be much faster

Chemoenzymatic dynamic kinetic resolution of primary amines catalyzed by CAL-B at 38-40°c

The (R)-selective chemoenzymatic dynamic kinetic resolution of primary amines was performed at 38-40 °C in MTBE, in good to high yields and with high enantiomeric excesses. These reactions associating CAL-B to octanethiol as radical racemizing agent were carried out in the presence of methyl β-methoxy propanoate as acyl donor, under photochemical irradiation at 350 nm in glassware.

Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization

Chemoenzymatic dynamic kinetic resolution (DKR) of amines involving sulfanyl radical-induced racemization happened to be the very first switchable DKR process allowing the synthesis of either (R)- or (S)-amides, in good yield and high enantiomeric excess,

N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate

Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h. The 2008 Royal Society of Chemistry.