2217-40-5

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3,4-Tetrahydro-1-naphthylamine is used as a reagent for the iodocyclization of 4-aryl-4-pentenoic acids, which is a crucial step in the synthesis of various pharmaceutical compounds. Its efficiency in this process makes it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
1,2,3,4-Tetrahydro-1-naphthylamine is used as a building block in the preparation of new chiral phosphine-aminophosphine ligands. These ligands are essential in various chemical reactions, particularly in asymmetric catalysis, where they help to achieve high selectivity and enantiomeric excess.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 1,2,3,4-Tetrahydro-1-naphthylamine is also utilized in research and development for the exploration of new synthetic pathways and the creation of novel compounds with potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H13N/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10H,3,5,7,11H2/p+1/t10-/m0/s1

Upstream product

• 68253-36-1 1-tetralone oxime 
• 77287-34-4 formamide 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 
• 832684-26-1 (+/-)-1-azido-1,2,3,4-tetrahydronaphthalene 
• 134-32-7 1-amino-naphthalene 
• 86-57-7 1-Nitronaphthalene 
• 3349-64-2 1-tetralone oxime 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 119-64-2 tetralin 
• 100-46-9 benzylamine 
• 5176-28-3 N-Boc-7-azabenzobicyclo[2.2.1]heptadiene 
• 1559065-85-8 N-chloro-3,4-dihydronaphthyl-1(2H)-imine 

Downstream Products

• 58490-01-0 1-(4-Chloro-phenyl)-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 59376-68-0 1-(4-Methoxy-benzyl)-3-(1,2,3,4-tetrahydro-naphthalen-1-yl)-urea 
• 114352-02-2 (S)-1,2,3,4-tetrahydro-1-naphthylamine hydrogen D-tartrate 
• 79817-66-6 1-nitro-1,2,3,4-tetrahydronaphthalene 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 129295-67-6 2-phenyl-N-(1,2,3,4-tetrahydro-naphthalen-1-yl)acetamide 
• 23357-52-0 (S)-1,2,3,4-tetrahydronapht-1-yl-amine 
• 23357-46-2 (R)-1,2,3,4-Tetrahydro-1-naphthylamine 
• 3349-64-2 1-tetralone oxime 
• 10409-15-1 (-)-N-methyl-1,2,3,4-tetrahydro-1-naphthylamine 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant academic research and scientific papers

A novel chimeric amine dehydrogenase shows altered substrate specificity compared to its parent enzymes

We created a novel chimeric amine dehydrogenase (AmDH) via domain shuffling of two parent AmDHs ('L- and F-AmDH'), which in turn had been generated from leucine and phenylalanine DH, respectively. Unlike the parent proteins, the chimeric AmDH ('cFL-AmDH') catalyzes the amination of acetophenone to (R)-methylbenzylamine and adamantylmethylketone to adamantylethylamine.

Preparation de cations chiraux (η5-cyclopentadienyl fer η6-arene)+ comportant une fonction oxime ou cetone en α du ligande arene, reduction electrochimique en amine ou en alcool optiquement actifs

Treatment of the species formed by deprotonation of the (η5-cyclopentadienylη6-tetraliniron) cation with the chiral alkyl nitrite (menthyl nitrite) yields the optically active (η5-cyclopentadienyl-η6-α-tetralono

Palladium/Lewis Acid Co-catalyzed Divergent Asymmetric Ring-Opening Reactions of Azabenzonorbornadienes with Alcohols

By fine tuning the combinations of chiral palladium catalysts and Lewis acids, both the additional and reductive asymmetric ring-opening reactions of azabenzonorbornadienes with alcohols were accomplished with good chemoselectivity, regioselectivity, and enantioselectivity. It was proven that the reductive ring-opening products were generated through a transfer-hydrogenation process with alcohols as hydrogen source.

Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(iii) complexes bearing an amidato ligand

A series of half-sandwich Ir(iii) complexes1-6bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex1, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Asymmetric transformation was also attempted with chiral Ir complexes3-6, and 16% ee of the desired primary amine was obtained. Despite the unsatisfactory enantio-control achieved so far, the current exploration might stimulate more efforts towards the discovery of better chiral catalysts for this challenging but important transformation.

Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones

Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.

Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant

The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.

CXCR2 ANTAGONIST

A compound as a CXCR2 antagonist and an application thereof in preparing a drug as a CXCR2 antagonist. In particular, the present invention relates to a compound represented by formula (II) or an isomer or pharmaceutically acceptable salt thereof.

Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

Rapid and Quantitative Profiling of Substrate Specificity of ω-Transaminases for Ketones

ω-Transaminases (ω-TAs) have gained growing attention owing to their capability for asymmetric synthesis of chiral amines from ketones. Reliable high-throughput activity assay of ω-TAs is essential in carrying out extensive substrate profiling and establishing a robust screening platform. Here we report spectrophotometric and colorimetric methods enabling rapid quantitation of ω-TA activities toward ketones in a 96-well microplate format. The assay methods employ benzylamine, a reactive amino donor for ω-TAs, as a cosubstrate and exploit aldehyde dehydrogenase (ALDH) as a reporter enzyme, leading to formation of benzaldehyde detectable by ALDH owing to concomitant NADH generation. Spectrophotometric substrate profiling of two wild-type ω-TAs of opposite stereoselectivity was carried out at 340 nm with 22 ketones, revealing subtle differences in substrate specificities that were consistent with docking simulation results obtained with cognate amines. Colorimetric readout for naked eye detection of the ω-TA activity was also demonstrated by supplementing the assay mixture with color-developing reagents whose color reaction could be quantified at 580 nm. The colorimetric assay was applied to substrate profiling of an engineered ω-TA for 24 ketones, leading to rapid identification of reactive ketones. The ALDH-based assay is expected to be promising for high-throughput screening of enzyme collections and mutant libraries to fish out the best ω-TA candidate as well as to tailor enzyme properties for efficient amination of a target ketone.

N-Alkylation of Aqueous Ammonia with Alcohols Leading to Primary Amines Catalyzed by Water-Soluble N-Heterocyclic Carbene Complexes of Iridium

A new catalytic system for the N-monoalkylation of aqueous ammonia with a variety of alcohols was developed. Water-soluble dicationic complexes of iridium bearing N-heterocyclic carbene and diammine ligands exhibited high catalytic activity for this type of reaction on the basis of hydrogen-transfer processes without generating harmful or wasteful byproducts. Various primary amines were efficiently synthesized by using safe, inexpensive, and easily handled aqueous ammonia as a nitrogen source. For example, the reaction of 1-(4-methylphenyl)ethanol with aqueous ammonia in the presence of a water-soluble N-heterocyclic carbene complex of iridium at 150 °C for 40 h gave 1-(4-methylphenyl)ethylamine in 83 % yield.