199186-69-1

Basic information

• Product Name: (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline
• Synonyms: (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS NO: 199186-69-1
• Molecular Formula: C₁₀H₁₂FN
• Molecular Weight: 165
• Mol File: 199186-69-1.mol
• Article Data: 43

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline(199186-69-1)
• EPA Substance Registry System: (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline(199186-69-1)

Safety Data

• Hazardous Substances Data: 199186-69-1(Hazardous Substances Data)

Usage

General Description

(R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline is a chemical compound with the molecular formula C10H12FNO. It is a tetrahydroquinoline derivative with a fluorine substituent at the 6-position and a methyl group at the 2-position. (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline is a chiral molecule, with a stereogenic center at the 2-position. Tetrahydroquinolines are commonly found in natural products and pharmaceuticals, and they exhibit a wide range of biological activities. The presence of a fluorine atom in (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline could potentially impart unique chemical and biological properties to this compound. Due to its structural features and potential biological activity, (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline may have applications in medicinal chemistry and drug development.

Upstream product

• 98-56-6 4-chlorobenzotrifluoride 
• 42835-89-2 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline 
• 623-03-0 4-Cyanochlorobenzene 
• 147851-69-2 (R)-2-phenoxypropionyl chloride 
• 54731-09-8 N-tosyl-L-prolyl chloride 
• 3183-10-6 N-phthalimide-L-leucinyl chloride 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 51091-84-0 (S)-naproxenoyl chloride 
• 1128-61-6 6-fluoro-2-methyl-quinoline 

Downstream Products

• 1128-61-6 6-fluoro-2-methyl-quinoline 
• 233765-85-0 9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester 
• 215178-95-3 R-(+)-flumequine 
• 233765-83-8 2-(6-fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester 

Relevant articles and documents

Resolution of the flumequine intermediate 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Racemic 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) was resolved by the N-phthaloyl derivative of the (R)-enantiomer. The enantiomeric mixture was very effectively enriched by recrystallisation from either the melt (working best for mixtures of relatively high starting enantiomeric purities) or from solution of its hydrochloride salt (giving good results when applied for mixtures of moderate to medium enantiomeric purities). Copyright (C) 2000 Elsevier Science Ltd.

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.

Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01

A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).