2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-mercaptopropyl]-alpha,alpha-dimethylbenzenemethanol

Base Information

• Chemical Name: 2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-mercaptopropyl]-alpha,alpha-dimethylbenzenemethanol
• CAS No.: 855473-49-3
• Molecular Formula: C₂₉H₂₈ClNOS
• Molecular Weight: 474.066
• European Community (EC) Number: 617-722-2
• DSSTox Substance ID: DTXSID801110620
• Mol file: 855473-49-3.mol

Synonyms:SCHEMBL1133011;SCHEMBL1133016;DTXSID801110620;2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-mercaptopropyl]-alpha,alpha-dimethylbenzenemethanol;855473-49-3

Chemical Property of 2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-mercaptopropyl]-alpha,alpha-dimethylbenzenemethanol

Chemical Property:

• XLogP3: 7.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 473.1580134
• Heavy Atom Count: 33
• Complexity: 639

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C1=CC=CC=C1CCC(C2=CC=CC(=C2)C=CC3=NC4=C(C=CC(=C4)Cl)C=C3)S)O
• Isomeric SMILES: CC(C)(C1=CC=CC=C1CC[C@H](C2=CC=CC(=C2)/C=C/C3=NC4=C(C=CC(=C4)Cl)C=C3)S)O

Technology Process of 2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-mercaptopropyl]-alpha,alpha-dimethylbenzenemethanol

There total 2 articles about 2-[(3R)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-mercaptopropyl]-alpha,alpha-dimethylbenzenemethanol 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: 93.0%

(3R)-{3-[(E)-2-(7-chloro-2-quinolinyl)vinyl]phenyl}-4,5-dihydro-3H-benzo[c]thiepin-1-one (937366-40-0) → C29H28ClNOS (855473-49-3)

Guidance literature:

methylmagnesium chloride; With cerium(III) chloride; In tetrahydrofuran; at 0 - 20 ℃; for 2.58333h;

(3R)-{3-[(E)-2-(7-chloro-2-quinolinyl)vinyl]phenyl}-4,5-dihydro-3H-benzo[c]thiepin-1-one; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 1.08333h;

With hydrogenchloride; water; In tetrahydrofuran; toluene; at 20 ℃; for 0.25h; pH=4 - 5; Product distribution / selectivity;

Reference yield:

methyl magnesium iodide (917-64-6) + (R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate (855473-48-2) → C29H28ClNOS (855473-49-3)

Guidance literature:

(R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate; lanthanum(III) chloride; lithium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 1h;

methyl magnesium iodide; In tetrahydrofuran; diethyl ether; toluene; at -10 - 25 ℃;

With ammonium chloride; In tetrahydrofuran; diethyl ether; toluene;

Reference yield:

C29H28ClNOS (855473-49-3) → Montelukast sodium (151767-02-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / N,N-dimethyl-formamide; methanol / 1 h / -10 °C

1.2: 20 °C

2.1: sodium hydroxide / tetrahydrofuran; methanol / 25 h / 5 - 20 °C / Industry scale

2.2: Industry scale

3.1: sodium hydroxide / toluene; ethanol / 2.5 h / 0 - 30 °C / Industry scale

With sodium methylate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(3R)-{3-[(E)-2-(7-chloro-2-quinolinyl)vinyl]phenyl}-4,5-dihydro-3H-benzo[c]thiepin-1-one

methyl magnesium iodide

(R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate

Downstream raw materials:

C₇H₈O₃S*C₂₉H₂₈ClNOS

1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropane acetic acid methyl ester

montelukast

Montelukast sodium