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

Base Information

• Chemical Name: (2S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 199186-68-0
• Molecular Formula: C10H12FN
• Molecular Weight: 165.21
• Hs Code.: 29339900
• DSSTox Substance ID: DTXSID60357401
• Nikkaji Number: J1.113.732F
• Wikidata: Q82137297
• ChEMBL ID: CHEMBL4441546
• Mol file: 199186-68-0.mol

Synonyms:199186-68-0;(S)-6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline;(2S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline;SCHEMBL3813452;CHEMBL4441546;DTXSID60357401;AKOS026675737;TS-02220

Chemical Property of (2S)-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:

99%, ^*data from raw 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 (2S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

There total 11 articles about (2S)-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: 81.0%

6-fluoro-2-methyl-quinoline (1128-61-6) → (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1) + (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-68-0)

Guidance literature:

With (S)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; dibenzyl hantzsch ester; In benzene; at 60 ℃; optical yield given as %ee;

DOI:10.1016/j.tet.2010.04.091

Reference yield: 54.0%

N-phthalimide-L-leucinyl chloride (3183-10-6) + 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (42835-89-2) → (2S)-6-fluoro-2-methyl-N-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline + (2R)-6-fluoro-2-methyl-N-[N'-phthaloyl-(S)-leucyl]-1,2,3,4-tetrahydroquinoline + (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1) + (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-68-0)

Guidance literature:

In dichloromethane; at -20 ℃; for 6h; Temperature; Resolution of racemate;

DOI:10.1016/j.tetasy.2013.07.024

Reference yield: 46.0%

6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (42835-89-2) + phthaloyl-L-phenylalanyl chloride (32150-91-7) → (2S)-6-fluoro-2-methyl-N-[N'-phthaloyl-(S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline + (2R)-6-fluoro-2-methyl-N-[N'-phthaloyl-(S)-phenylalanyl]-1,2,3,4-tetrahydroquinoline + (R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1) + (S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-68-0)

Guidance literature:

In dichloromethane; at -20 ℃; for 6h; Temperature; Resolution of racemate;

DOI:10.1016/j.tetasy.2013.07.024

upstream raw materials:

6-fluoro-2-methyl-quinoline

(S)-naproxenoyl chloride

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

phthaloyl-L-phenylalanyl chloride

Downstream raw materials:

S-(-)-flumequine

Refernces

• 1、 Xia, Yun-Tao,Ma, Jing,Wang, Xiao-Dong,Yang, Lei,Wu, Lei. "Enantioselective hydrogenation of N-heteroaromatics catalyzed by chiral diphosphine modified binaphthyl palladium nanoparticles". . p. 5515 - 5520. Retrieved 2017/12/07.
• 2、 John, Joshni,Wilson-Konderka, Cody,Metallinos, Costa. "Low Pressure Asymmetric Hydrogenation of Quinolines using an Annulated Planar Chiral N-Ferrocenyl NHC-Iridium Complex". . p. 2071 - 2081. Retrieved 2015/06/23.