(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol

Base Information

• Chemical Name: (2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol
• CAS No.: 121660-11-5
• Molecular Formula: C19H16FNO
• Molecular Weight: 293.341
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID60431270
• Nikkaji Number: J1.195.491J
• Wikidata: Q72460882
• Mol file: 121660-11-5.mol

Synonyms:121660-11-5;(2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol;2-Cyclopropyl-4-(4-fluorophenyl)-quinolyl-3-methanol;2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinemethanol;3-Quinolinemethanol, 2-cyclopropyl-4-(4-fluorophenyl)-;[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol;MFCD09032924;2-Cyclopropyl-4-(4-fluorophenyl)quinoline-3-methanol;1346600-49-4;Pitavastatin Hydroxymethyl;SCHEMBL31546;2-cyclopropan-4-(4-fluorophenyl)-3-quinoline methanol;AMY4153;DTXSID60431270;BCP07795;AKOS015900378;AC-2056;SB71698;DS-12057;SY042631;CS-0156033;FT-0645359;A24866;D84156;J-509251;[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]methanol;(2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-yl)methanol;2-Cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline;-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinemethanol;4-(4-Fluorophenyl)-2-(cyclopropyl)-3-quinolinemethanol;[2-Cyclopropyl-4-(p-fluorophenyl)-3-quinolyl]methanol;2-Cyclopropyl-3-(hydroxymethyl)-4-(4-fluorophenyl)quinoline;2-Cyclopropyl-4-(4'-fluorophenyl) quinolyl-3-methanol;[2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]methanol

Chemical Property of (2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.671
• Boiling Point: 474.749 ºC at 760 mmHg
• Flash Point: 240.919 ºC
• PSA: 33.12000
• Density: 1.286 g/cm³
• LogP: 4.41060
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 293.121592296
• Heavy Atom Count: 22
• Complexity: 378

Purity/Quality:

≥98.0% ^*data from raw suppliers

PT 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2CO)C4=CC=C(C=C4)F
• Uses: Pitavastatin intermediate.

Technology Process of (2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol

There total 17 articles about (2-Cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)methanol 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: 100.0%

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline (121660-37-5) → 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5)

Guidance literature:

With borohydride anion exchange resin (BER); In ethanol; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2015.05.053

Reference yield: 98.3%

2-cyclopropyl-4-(4-fluoro-phenyl)-3-quinoline carboxylic acid ethyl ester (148516-11-4) → 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5)

Guidance literature:

With potassium borohydride; magnesium chloride; In tetrahydrofuran; toluene; at 100 ℃; for 10h;

DOI:10.1016/j.tetlet.2007.08.118

Reference yield: 93.0%

methyl 4-(4'-fluorophenyl)-2-cyclopropylquinoline-3-carboxylate (121659-86-7) → 2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at 0 ℃; for 2h;

DOI:10.1021/jacs.5b09342

upstream raw materials:

2-cyclopropyl-4-(4-fluoro-phenyl)-3-quinoline carboxylic acid ethyl ester

methyl 4-(4'-fluorophenyl)-2-cyclopropylquinoline-3-carboxylate

2-amino-4'-fluorobenzophenone

methyl 3-cyclopropyl-3-oxopropanoate

Downstream raw materials:

3-(bromomethyl)-2-cyclopropyl-4-(4-fluorophenyl)-quinoline

pitavastatin calcium salt

<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>methyltriphenylphosphonium bromide

sodium (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate

Refernces

• 1、 Spreider, Pierre A.,Breit, Bernhard. "Palladium-Catalyzed Stereoselective Cyclization of in Situ Formed Allenyl Hemiacetals: Synthesis of Rosuvastatin and Pitavastatin". supporting information. p. 3286 - 3290. Retrieved 2018/06/11.
• 2、 Makarov, Ilya S.,Kuwahara, Takashi,Jusseau, Xavier,Ryu, Ilhyong,Lindhardt, Anders T.,Skrydstrup, Troels. "Palladium-Catalyzed Carbonylative Couplings of Vinylogous Enolates: Application to Statin Structures". supporting information. p. 14043 - 14046. Retrieved 2015/11/25.