(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile

Base Information

• Chemical Name: (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile
• CAS No.: 256431-72-8
• Molecular Formula: C21H15FN2
• Molecular Weight: 314.362
• Hs Code.: 2933499090
• European Community (EC) Number: 607-769-7
• DSSTox Substance ID: DTXSID701152596
• Nikkaji Number: J1.646.459G
• Mol file: 256431-72-8.mol

Synonyms:256431-72-8;(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile;(E)-3-(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)acrylonitrile;(E)-3-(2-Cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)acrylonitrile;(E)-3-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]prop-2-enenitrile;C21H15FN2;(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propopenenitrile;2-Propenenitrile, 3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-, (2E)-;BFDPBLWCXIOOLM-HWKANZROSA-N;DTXSID701152596;MFCD11042688;AKOS015900477;AC-2058;DS-5726;CS-0156041;D82572;A817943;(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]propenenitrile;(2E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile

Chemical Property of (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.686
• Boiling Point: 494.251 °C at 760 mmHg
• PKA: 3.78±0.50(Predicted)
• Flash Point: 252.714 °C
• PSA: 36.68000
• Density: 1.264 g/cm³
• LogP: 5.45508
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 314.12192665
• Heavy Atom Count: 24
• Complexity: 509

Purity/Quality:

99% ^*data from raw suppliers

(E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2C=CC#N)C4=CC=C(C=C4)F
• Isomeric SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2/C=C/C#N)C4=CC=C(C=C4)F

Technology Process of (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile

There total 7 articles about (E)-3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile 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:

2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinoline-3-carbaldehyde (121660-43-3) → (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile (256431-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

2.1: 85.1 percent / aq. NaOH; trioctylmethylammonium chloride / toluene / 2 h / 20 °C

With sodium hydroxide; n-butyllithium; Aliquat 336; In tetrahydrofuran; hexane; toluene; 2.1: Emmons-Horner coupling;

DOI:10.1016/S0968-0896(01)00198-5

Reference yield:

[2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinolin-3-yl]-methanol (121660-18-2) → (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile (256431-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

2.2: tetrahydrofuran; hexane / -78 °C

3.1: 85.1 percent / aq. NaOH; trioctylmethylammonium chloride / toluene / 2 h / 20 °C

With sodium hydroxide; n-butyllithium; sodium acetate; Aliquat 336; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Emmons-Horner coupling;

DOI:10.1016/S0968-0896(01)00198-5

Reference yield:

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5) → (E)-3-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-2-propenenitrile (256431-72-8)

Guidance literature:

Multi-step reaction with 2 steps

1: DMSO; P₂O₅; Et₃N

2: NaOH; (n-octyl)3MeNCl / toluene; H₂O

With sodium hydroxide; phosphorus pentoxide; Aliquat 336; dimethyl sulfoxide; triethylamine; In water; toluene; 1: Oxidation / 2: Condensation;

DOI:10.1016/S0960-894X(99)00519-3

upstream raw materials:

diethyl 1-cyanomethylphosphonate

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinoline-3-carbaldehyde

[2-cyclopropyl-4-(4-fluoro-phenyl)-6,7-dimethoxy-quinolin-3-yl]-methanol

Downstream raw materials:

(E)-(S)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid (S)-2-hydroxy-1,2,2-triphenyl-ethyl ester

(E)-(R)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic acid (R)-2-hydroxy-1,2,2-triphenyl-ethyl ester

ethyl 5(S)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate

ethyl 5(R)-(E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxo-6-heptenoate

Refernces

• 1、 Suzuki,Iwasaki,Fujikawa,Kitahara,Sakashita,Sakoda. "Synthesis and biological evaluations of quinoline-based HMG-CoA reductase inhibitors". . p. 2727 - 2743. Retrieved 2007/10/03.