(8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline

Base Information

• Chemical Name: (8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline
• CAS No.: 175410-67-0
• Molecular Formula: C₁₅H₁₄ClN
• Molecular Weight: 243.736
• Mol file: 175410-67-0.mol

Synonyms:(8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline

Chemical Property of (8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline

There total 5 articles about (8R)-2-chloro-8-phenyl-5,6,7,8-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: 58.0%

Thiocarbonic acid O-((7R,8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydro-quinolin-7-yl) ester O-phenyl ester (175410-78-3) → (8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline (175410-67-0)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In tetrahydrofuran; benzene; for 12h; Ambient temperature;

DOI:10.1016/S0040-4020(96)00058-0

Reference yield:

2-chloro-5,6,7,8-tetrahydro-quinoline (21172-88-3) → (8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline (175410-67-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LDA, 2.) PhSSPh, 3.) mCPBA

2: 73 percent / 4-phenylpyridine-N-oxide, Mn-salen complex, aq. NaClO, phosphate buffer / CH₂Cl₂ / 3 h

3: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) cyclohexane, ether, THF, -10 deg C, 5 min, 2.) cyclohexane, ether, THF, -78 deg C, 2 h

4: 68 percent / DMAP / acetonitrile / 3 h / Ambient temperature

5: 58 percent / tributyltinhydride, triethylborane / tetrahydrofuran; benzene / 12 h / Ambient temperature

With dmap; sodium hypochlorite; 4-Phenylpyridine 1-oxide; phosphate buffer; 2,2′-((1E,1′E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))diphenolmanganese(II); triethyl borane; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; diphenyldisulfane; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4020(96)00058-0

Reference yield:

2-chloro-5,6-dihydroquinoline → (8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydroquinoline (175410-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / 4-phenylpyridine-N-oxide, Mn-salen complex, aq. NaClO, phosphate buffer / CH₂Cl₂ / 3 h

2: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) cyclohexane, ether, THF, -10 deg C, 5 min, 2.) cyclohexane, ether, THF, -78 deg C, 2 h

3: 68 percent / DMAP / acetonitrile / 3 h / Ambient temperature

4: 58 percent / tributyltinhydride, triethylborane / tetrahydrofuran; benzene / 12 h / Ambient temperature

With dmap; sodium hypochlorite; 4-Phenylpyridine 1-oxide; phosphate buffer; 2,2′-((1E,1′E)-(ethane-1,2-diylbis(azanylylidene))bis(methanylylidene))diphenolmanganese(II); triethyl borane; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4020(96)00058-0

upstream raw materials:

Thiocarbonic acid O-((7R,8R)-2-chloro-8-phenyl-5,6,7,8-tetrahydro-quinolin-7-yl) ester O-phenyl ester

2-chloro-5,6,7,8-tetrahydro-quinoline

(7R,8S)-2-chloro-7,8-epoxy-5,6,7,8-tetrahydroquinoline

(7R,8R)-2-chloro-7-hydroxy-8-phenyl-5,6,7,8-tetrahydroquinoline