(R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 199186-69-1
• Molecular Formula: C10H12FN
• Molecular Weight: 165.21
• Nikkaji Number: J1.113.731H
• ChEMBL ID: CHEMBL4559367
• Mol file: 199186-69-1.mol

Synonyms:(R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline;199186-69-1;(2R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline;CHEMBL4559367;SCHEMBL14943839;AKOS006306940;(2R)-2-Methyl-6-fluoro-1,2,3,4-tetrahydroquinoline

Chemical Property of (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• PSA: 12.03000
• LogP: 2.71030
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 165.095377549
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

98%min ^*data from raw suppliers

(R)-6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=C(N1)C=CC(=C2)F
• Isomeric SMILES: C[C@@H]1CCC2=C(N1)C=CC(=C2)F

Technology Process of (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

There total 17 articles about (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

6-fluoro-2-methyl-quinoline (1128-61-6) → (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1)

Guidance literature:

With C₃₄H₃₉F₃N₂O₅RuS₂; hydrogen; In methanol; at 25 ℃; for 14h; under 38002.6 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1021/ja2023042

Reference yield: 96.0%

→ (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1)

Guidance literature:

With C₆₆H₈₂IrN₂O₁₀P₂⁽¹⁺⁾*BF₄^(1-); hydrogen; In ethyl acetate; at 20 ℃; for 24h; under 38002.6 Torr;

Reference yield: 94.0%

(2R,2'S)-6-fluoro-2-methyl-N-(N'-tosylprolyl)-1,2,3,4-tetrahydroquinoline → (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1)

Guidance literature:

With ethanol; sodium ethanolate; Reflux;

DOI:10.1021/acsmedchemlett.8b00540

upstream raw materials:

6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline

6-fluoro-2-methyl-quinoline

(S)-naproxenoyl chloride

phthaloyl-L-phenylalanyl chloride

Downstream raw materials:

9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester

R-(+)-flumequine

6-fluoro-2-methyl-quinoline

2-(6-fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester

Refernces

• 1、 Ren, Yiqi,Tao, Lin,Li, Chunzhi,Jayakumar, Sanjeevi,Li, He,Yang, Qihua. "Development of efficient solid chiral catalysts with designable linkage for asymmetric transfer hydrogenation of quinoline derivatives". . p. 1576 - 1585. Retrieved 2021/05/10.
• 2、 Hu, Ziwei,Banothu, Janardhan,Beesu, Mallesh,Gustafson, Collin J.,Brush, Michael J. H.,Trautman, Kathryn L.,Salyer, Alex C. D.,Pathakumari, Balaji,David, Sunil A.. "Identification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine-Quinolone Carboxamides". supporting information. p. 132 - 136. Retrieved 2019/01/15.