63430-95-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2α-Methyl-1,2,3,4-tetrahydroquinoline is used as a potential ligand for neurotransmitter receptors due to its interaction with these receptors, which may contribute to its neuroprotective effects and potential use in treating neurological disorders.
Used in Neuroscience Research:
(R)-2α-Methyl-1,2,3,4-tetrahydroquinoline is used as a research compound for studying its neuroprotective properties, which could lead to the development of new therapies for neurodegenerative diseases.
Used in Oncology Research:
(R)-2α-Methyl-1,2,3,4-tetrahydroquinoline is used as a potential anti-cancer agent for its ability to inhibit the growth of certain cancer cells, indicating its potential use in cancer treatment strategies.
Used in Drug Development:
(R)-2α-Methyl-1,2,3,4-tetrahydroquinoline is used as a lead compound in the development of new pharmaceuticals, given its demonstrated pharmacological properties and potential for further optimization in drug design.

Upstream product

• 54731-09-8 N-tosyl-L-prolyl chloride 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 91-63-4 2-methylquinoline 
• 1239896-95-7 N-phthaloyl-(S)-2-phenylglycyl chloride 
• 4306-25-6 (S)-2-phthalimidopropionyl chloride 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 1076-28-4 2-methylquinoline N-oxide 
• 457622-20-7 4-(2-aminophenyl)-2-butanol 
• 147851-69-2 (R)-2-phenoxypropionyl chloride 
• 1435-43-4 1-chloro-3,5-difluorobenzene 
• 91-58-7 2-chloronaphthalene 
• 2051-62-9 4'-biphenyl chloride 
• 108-90-7 chlorobenzene 
• 98-56-6 4-chlorobenzotrifluoride 

Downstream Products

• 1239897-01-8 (2R)-2-methyl-N-[N-phthaloyl-(2S)-2-phenylglycyl]-1,2,3,4-tetrahydroquinoline 
• 1239897-00-7 (2R)-2-methyl-N-[N-phthaloyl-(2S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline 
• 1186392-43-7 2-methyl-1,2,3,4-tetrahydroquinoline phosphoramidite 
• 36191-13-6 (2R,4R)-2-methyl-1,2,3,4-tetrahydroquinoline-4-ol 
• 1619901-87-9 C₃₀H₂₄NO₂P 
• 1619901-87-9 C₃₀H₂₄NO₂P 

Relevant academic research and scientific papers

Development of efficient solid chiral catalysts with designable linkage for asymmetric transfer hydrogenation of quinoline derivatives

This vertically self-pillared (VSP) structure extends the application range of traditional porous materials with facile mass/ion transport and enhanced reaction kinetics. Here, we prepare a single crystal metal-organic framework (MOF), employing the ZIF-67 structure as a proof of concept, which is constructed by vertically self-pillared nanosheets (VSP-MOF). We further converted VSP-MOF into VSP-cobalt sulfide (VSP-CoS2) through a sulfidation process. Catalysis plays an important role in almost all battery technologies; for metallic batteries, lithium anodes exhibit a high theoretical specific capacity, low density, and low redox potential. However, during the half-cell reaction (Li++e=Li), uncontrolled dendritic Li penetrates the separator and solid electrolyte interphase layer. When employed as a composite scaffold for lithium metal deposition, there are many advantage to using this framework: 1) the VSP-CoS2 substrate provides a high specific surface area to dissipate the ion flux and mass transfer and acts as a pre-catalyst, 2) the catalytic Co center favors the charge transfer process and preferentially binds the Li+ with the enhanced electrical fields, and 3) the VSP structure guides the metallic propagation along the nanosheet 2D orientation without the protrusive dendrites. All these features enable the VSP structure in metallic batteries with encouraging performances.

Low-Temperature Nickel-Catalyzed C?N Cross-Coupling via Kinetic Resolution Enabled by a Bulky and Flexible Chiral N-Heterocyclic Carbene Ligand

The transition-metal-catalyzed C?N cross-coupling has revolutionized the construction of amines. Despite the innovations of multiple generations of ligands to modulate the reactivity of the metal center, ligands for the low-temperature enantioselective amination of aryl halides remain a coveted target of catalyst engineering. Designs that promote one elementary reaction often create bottlenecks at other steps. We here report an unprecedented low-temperature (as low as ?50 °C), enantioselective Ni-catalyzed C?N cross-coupling of aryl chlorides with sterically hindered secondary amines via a kinetic resolution process (s factor up to >300). A bulky yet flexible chiral N-heterocyclic carbene (NHC) ligand is leveraged to drive both oxidative addition and reductive elimination with low barriers and control the enantioselectivity. Computational studies indicate that the rotations of multiple σ-bonds on the C2-symmetric chiral ligand adapt to the changing needs of catalytic processes. We expect this design would be widely applicable to diverse transition states to achieve other challenging metal-catalyzed asymmetric cross-coupling reactions.

Alternative Strategy to Obtain Artificial Imine Reductase by Exploiting Vancomycin/D-Ala-D-Ala Interactions with an Iridium Metal Complex

Based on the supramolecular interaction between vancomycin (Van), an antibiotic glycopeptide, and D-Ala-D-Ala (DADA) dipeptides, a novel class of artificial metalloenzymes was synthesized and characterized. The presence of an iridium(III) ligand at the N-terminus of DADA allowed the use of the metalloenzyme as a catalyst in the asymmetric transfer hydrogenation of cyclic imines. In particular, the type of link between DADA and the metal-chelating moiety was found to be fundamental for inducing asymmetry in the reaction outcome, as highlighted by both computational studies and catalytic results. Using the [IrCp*(m-I)Cl]Cl Van complex in 0.1 M CH3COONa buffer at pH 5, a significant 70% (S) e.e. was obtained in the reduction of quinaldine B.

Manganese-Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π–π Interaction**

The non-noble metal-catalyzed asymmetric hydrogenation of N-heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asymmetric hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97 % ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which is competitive with the activity of most effective noble metal catalysts for this reaction. The precise regulation of the enantioselectivity were ensured by a π–π interaction.

Enantiodivergent Synthesis of Chiral Tetrahydroquinoline Derivatives via Ir-Catalyzed Asymmetric Hydrogenation: Solvent-Dependent Enantioselective Control and Mechanistic Investigations

Ir-catalyzed asymmetric hydrogenation of quinolines was developed, and both enantiomers of chiral tetrahydroquinoline derivatives could be easily obtained, respectively, in high yields with good enantioselectivities through the adjustment of reaction solvents (toluene/dioxane: up to 99% yield, 98% ee (R), TON = 680; EtOH: up to 99% yield, 94% ee (S), TON = 1680). It provided an efficient and simple synthetic strategy for the enantiodivergent synthesis of chiral tetrahydroquinolines, and gram-scale asymmetric hydrogenation proceeded well with low-catalyst loading in these two reaction systems. A series of deuterium-labeling experiments, control experiments, and 1H NMR and electrospray ionization-mass spectrometry experiments have been conducted, and a reasonable and possible reaction process was revealed on the basis of these useful observations.

Exploration of chiral diastereomeric spiroketal (SPIROL)-based phosphinite ligands in asymmetric hydrogenation of heterocycles

New and readily available chiral SPIROL-based diphosphinite ligands (SPIRAPO) have been prepared and employed for iridium-catalyzed asymmetric hydrogenations of quinolines, quinoxalines and 2H-1,4-bezoxazin-2-ones. While the structurally similar (R,R,R)-SPIRAPO and (R)-SPINOL-based phosphinites were not the best ligands for these transformations, the (S,R,R)-diastereomer of SPIRAPO was found to be highly effective ligand for the reduction of 20 different heterocyclic systems with loadings as low as S/C = 10?000. This dearomatizative hydrogenation provided direct access to optically active tetrahydroquinolines in high enantioselectivities (up to 94percent ee) and excellent yields (up to 99percent), and was used to generate 1.75 g of natural alkaloid (-)-(R)-angustureine. This protocol was subsequently extended to achieve asymmetric hydrogenation of quinoxalines and 2H-1,4-benzoxazin-2-ones in good to excellent enantioselectivities.

Enantioselective Synthesis of Tetrahydroquinolines via One-Pot Cascade Biomimetic Reduction?

A novel and efficient protocol for the synthesis of chiral tetrahydroquinoline derivatives with excellent enantioselectivities and high yields has been developed through one-pot cascade biomimetic reduction. The detailed reaction pathway includes the acid-catalyzed and ruthenium-catalyzed formation of aromatic quinoline intermediates and biomimetic asymmetric reduction.

Efficient Asymmetric Hydrogenation of Quinolines over Chiral Porous Polymers Integrated with Substrate Activation Sites

Heterogeneous asymmetric hydrogenation of quinolines for the production of optically active tetrahydroquinoline derivatives still remains a difficult task due to the aromatic stability of quinolines. Herein, we reported efficient heterogeneous asymmetric hydrogenation of quinolines over chiral porous polymers integrated with both chiral active sites (VDPEN-RuOTs) and substrate activation sites (TsOH). The porous polymer integrated with TsOH is 10 times more active than that without TsOH in the asymmetric hydrogenation of 2-methylquinoline. The volcano curve of TOF with the TsOH/Ru ratio confirms the synergistic catalysis of VDPEN-RuOTs and TsOH. Comparison results with a homogeneous catalytic system imply that the synergy between chiral centers and acidic sites is greatly enhanced in the polymer network. Under optimized conditions, the chiral porous polymer afforded up to 90% ee with 90 h-1 TOF, which is one of the best solid catalysts for asymmetric hydrogenation of quinoline derivatives ever reported. Furthermore, the bifunctional porous polymers realized the asymmetric cascade hydrogenation/reductive amination reaction to obtain benzo-quinolizidines. Our primary results suggest that the incorporation of substrate activation sites near chiral centers is an efficient strategy for the synthesis of high-performance solid catalysts for heterogeneous asymmetric catalysis.

Spiro-Bicyclic Bisborane Catalysts for Metal-Free Chemoselective and Enantioselective Hydrogenation of Quinolines

A new series of spiro-bicyclic bisborane catalysts has been prepared by means of hydroboration reactions of C2-symmetric spiro-bicyclic dienes with HB(C6F5)2 and HB(p-C6F4H)2. When used for hydrogenation of quinolines, these catalysts give excellent yields and enantiomeric excesses, and show turnover numbers of up to 460. The most attractive feature of these metal-free hydrogenation reactions was the broad functional-group tolerance, making this method complementary to existing methods for quinoline hydrogenation.

Synthesis of spiro-ring bis-boron catalyst and application thereof in hydrogenation reaction

The invention relates to a synthesis of spiro-ring diene compound with C2 symmetry, and a a series of chirality spiro-ring bis-boron catalysts prepared by virtue of the reaction of the spiro-ring diene compound and boron hydrides. The spiro-ring bis-boron catalysts have high activity and enantioselectivity in the asymmetric hydrogenation reaction of quinoline compounds, and belong to the technicalfield of application. By adopting the synthesis of spiro-ring bis-boron catalyst and the application thereof in hydrogenation reaction, the problems of the traditional quinoline asymmetric hydrogenation reaction method that precious metal catalysts are used and the functional groups are poor in tolerance can be mainly solved, the nonmetal catalytic quinoline asymmetric hydrogenation reaction canbe realized, the reaction substrate range is wide, and the functional group tolerance is high. The synthesis of spiro-ring bis-boron catalyst and the application thereof in hydrogenation reaction areused in the medicine research and chemical production.