(S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 1159987-42-4
• Molecular Formula: C₁₅H₁₄ClN
• Molecular Weight: 243.736
• Mol file: 1159987-42-4.mol

Synonyms:(S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline

Chemical Property of (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline

There total 6 articles about (S)-7-chloro-2-phenyl-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%

5-chloro-2-(3-phenylprop-2-yn-1-yl)aniline (1159987-33-3) → (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline (1159987-42-4)

Guidance literature:

With methyl(triphenylphosphine)gold(I); (R)‐3,3′‐bis(9‐phenanthryl)‐1,1′‐binaphthalene‐2,2′‐diyl hydrogen phosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In toluene; at 25 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja903547q

Reference yield: 97.0%

7-chloro-2-phenyl-quinoline (61687-26-1) → (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline (1159987-42-4)

Guidance literature:

With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; at -10 ℃; enantioselective reaction; Green chemistry;

DOI:10.1016/j.tetasy.2015.09.005

Reference yield:

(E)-3-(2-amino-4-chlorophenyl)-1-phenylprop-2-en-1-one → (S)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline (1159987-42-4) + (R)-7-chloro-2-phenyl-1,2,3,4-tetrahydroquinoline

Guidance literature:

(E)-3-(2-amino-4-chlorophenyl)-1-phenylprop-2-en-1-one; With phenanthridine; diiodo(p-cymene)ruthenium(II) dimer; (R)-3,3'-bis[3,5-difluorophenyl]-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid; In 1,3,5-trimethyl-benzene; at 20 ℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Molecular sieve; Glovebox;

With hydrogen; In 1,3,5-trimethyl-benzene; at 40 ℃; under 25858.1 Torr; Overall yield = 66 percent; Overall yield = 32 mg; enantioselective reaction; Molecular sieve; Autoclave;

DOI:10.1002/cjoc.202000409

upstream raw materials:

5-chloro-2-(3-phenylprop-2-yn-1-yl)aniline

7-chloro-2-phenyl-quinoline

4-Chloro-2-nitrobenzaldehyde

acetophenone

Refernces

• 1、 Du, Yu-Liu,Hu, Yue,Zhu, Yi-Fan,Tu, Xi-Feng,Han, Zhi-Yong,Gong, Liu-Zhu. "Chiral Gold Phosphate Catalyzed Tandem Hydroamination/Asymmetric Transfer Hydrogenation Enables Access to Chiral Tetrahydroquinolines". . p. 4754 - 4759. Retrieved 2015/05/13.
• 2、 Han, Zhi-Yong,Xiao, Han,Chen, Xiao-Hua,Gong, Liu-Zhu. "Consecutive intramolecular hydroamination/asymmetric transfer hydrogenation under relay catalysis of an achiral gold complex/chiral Bronsted acid binary system". supporting information; experimental part. p. 9182 - 9183. Retrieved 2009/12/06.