200125-70-8

Basic information

• Product Name: S-2-Methyl-1,2,3,4-tetrahydro-quinoline
• Synonyms: S-2-Methyl-1,2,3,4-tetrahydro-quinoline;(S)-1,2,3,4-Tetrahydro-2-methylquinoline,99%e.e.
• CAS NO: 200125-70-8
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.21692
• Mol File: 200125-70-8.mol

Chemical Properties

• Boiling Point: 256.7±10.0 °C(Predicted)
• Appearance: /
• Density: 0.966±0.06 g/cm3(Predicted)
• PKA: 5.15±0.40(Predicted)
• CAS DataBase Reference: S-2-Methyl-1,2,3,4-tetrahydro-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: S-2-Methyl-1,2,3,4-tetrahydro-quinoline(200125-70-8)
• EPA Substance Registry System: S-2-Methyl-1,2,3,4-tetrahydro-quinoline(200125-70-8)

Safety Data

• Hazardous Substances Data: 200125-70-8(Hazardous Substances Data)

Upstream product

• 1076-28-4 2-methylquinoline N-oxide 
• 111210-69-6 O-methyl-N-phthaloyl-(S)-tyrosyl chloride 
• 1780-19-4 1,2,3,4-tetrahydro-2-methylquinoline 
• 32329-20-7 (RS)-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 5511-73-9 N-phthalimide l-valinyl chloride 
• 173208-57-6 (S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3,3-dimethyl-butyryl chloride 
• 1416453-17-2 N-phthaloyl-3-cyclohexyl-(S)-alanyl chloride 
• 4306-25-6 (S)-2-phthalimidopropionyl chloride 
• 3183-10-6 N-phthalimide-L-leucinyl chloride 
• 62763-89-7 quinaldine hydrochloride 
• 457622-20-7 4-(2-aminophenyl)-2-butanol 
• 98-56-6 4-chlorobenzotrifluoride 
• 108-90-7 chlorobenzene 

Downstream Products

• 16078-03-8 1-benzoyl-2-methyl-1,2,3,4-tetrahydroquinoline 
• 49849-64-1 1-(4-methylbenzenesulfonyl)-2-methyl-1,2,3,4-tetrahydroquinoline 
• 24223-26-5 2-methyl-1-(2-nitro-benzoyl)-1,2,3,4-tetrahydro-quinoline 
• 1290176-66-7 (2S)-2-methyl-1-[o-methyl-N-phthaloyl-(S)-tyrosyl]-1,2,3,4-tetrahydroquinoline 
• 1290176-64-5 (2S)-2-methyl-1-[3-(4-nitrophenyl)-N-phthaloyl-(S)-alanyl]-1,2,3,4-tetrahydroquinoline 
• 1402082-56-7 N-[(2S)-2-(4-isobutylphenyl)propionyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline 
• 1402082-58-9 N-[(2S)-2-phenylpropionyl]-(2S)-2-methyl-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

Highly enantioselective hydrogenation of quinolines under solvent-free or highly concentrated conditions

The phosphine-free chiral cationic Ru(OTf)(TsDPEN)(η6- cymene) complex was found to be an efficient catalyst for the enantioselective hydrogenation of quinolines under more environmentally friendly solvent-free or highly concentrated conditions

N-Phthaloyl-(S)-alanyl chloride as a chiral resolving agent for the kinetic resolution of heterocyclic amines

Acylation of heterocyclic amines with N-phthaloyl-(S)-alanyl chloride under kinetic resolution conditions resulted in the predominant formation of (S,S)-amides. The diastereoselectivity of resolution depended heavily on the structure of the resolved amine.

DUAL KINASE-BROMODOMAIN INHIBITORS

Provided herein are compounds of Formula (I) that are dual inhibitors of kinases and bromo-domain proteins. The disclosure also relates to pharmaceutical compositions containing such compounds, methods for using such compounds in the treatment of cancers, particularly, the treatment of multiple myeloma cancers, and to related uses.

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.

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.

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.

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.