(E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate

Base Information

• Chemical Name: (E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate
• CAS No.: 148901-69-3
• Molecular Formula: C27H26FNO4
• Molecular Weight: 447.506
• European Community (EC) Number: 604-664-8
• DSSTox Substance ID: DTXSID201122750
• Nikkaji Number: J1.647.208E
• Mol file: 148901-69-3.mol

Synonyms:148901-69-3;Ethyl (E)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate;(E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate;Dehydropitavastatin ethyl ester;Ethyl (E)-7-[2-cyclopropyl-4-(4-flurophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate;6-HEPTENOIC ACID, 7-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-3-QUINOLINYL]-5-HYDROXY-3-OXO-, ETHYL ESTER, (6E)-;(E)-ETHYL 7-(2-CYCLOPROPYL-4-(4-FLUOROPHENYL)-QUINOLIN-3-YL)-5-HYDROXY-3-OXOHEPT-6-ENOATE;ethyl (E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-5-hydroxy-3-oxohept-6-enoate;Ethyl(e)-7-[4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate;(E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoic Acid Ethyl Ester;254452-91-0;C27H26FNO4;SCHEMBL1582201;SCHEMBL1582204;DTXSID201122750;BCP10764;ETHYL (6E)-7-[2-CYCLOPROPYL-4-(4-FLUOROPHENYL)QUINOLIN-3-YL]-5-HYDROXY-3-OXOHEPT-6-ENOATE;MFCD11041029;AKOS015900425;AC-2060;Ethyl (E)-7-[2-cyclopropyl-4-(4-;AS-19281;CS-0151621;A24872;D97834;J-008532;J-520477;flurophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate;(E)-Ethyl7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate;Ethyl (6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoate;(E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoic acid ethyl ester

Chemical Property of (E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate

Chemical Property:

• Boiling Point: 651.3 °C at 760 mmHg
• PKA: 10.30±0.46(Predicted)
• Flash Point: 347.7 °C
• PSA: 76.49000
• Density: 1.268 g/cm³
• LogP: 5.20480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 447.18458647
• Heavy Atom Count: 33
• Complexity: 700

Purity/Quality:

99% ^*data from raw suppliers

(E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)CC(C=CC1=C(C2=CC=CC=C2N=C1C3CC3)C4=CC=C(C=C4)F)O
• Isomeric SMILES: CCOC(=O)CC(=O)CC(/C=C/C1=C(C2=CC=CC=C2N=C1C3CC3)C4=CC=C(C=C4)F)O
• Uses: (E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoic Acid Ethyl Ester is an impurity of Pitavastatin (P531000), a competitive inhibitor of HMG-CoA reductase and antilipemi c agent. (E)-7-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-5-hydroxy-3-oxo-6-heptenoic Acid Ethyl Ester is an impurity of Pitavastatin (P531000), a competitive inhibitor of HMG-CoA reductase and antilipemic agent.

Technology Process of (E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate

There total 12 articles about (E)-Ethyl 7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-5-hydroxy-3-oxohept-6-enoate 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: 83.5%

ethyl acetoacetate (141-97-9) + (E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal (148901-68-2,121660-63-7) → (E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxohept-6-enic acid ethyl ester (148901-69-3)

Guidance literature:

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; at -10 ℃; for 3h;

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

Reference yield:

(E)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dioxo-hept-6-enoic acid ethyl ester (166803-31-2) → C27H26FNO4 + (E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxohept-6-enic acid ethyl ester (148901-69-3) + (E)-(3R,5S)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester (167073-19-0,172336-32-2,172336-33-3)

Guidance literature:

With Rhodotorula glutinis var dairenensis IFO₀₄₁₅; In dimethyl sulfoxide; at 27 ℃; for 12h; pH=7; Product distribution / selectivity; aerobic conditions; potassium phosphate buffer (pH 7.0);

Reference yield:

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5) → (E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl]-5-hydroxy-3-oxohept-6-enic acid ethyl ester (148901-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 56.5 percent / pyridinium chlorochromate; sodium acetate / CH₂Cl₂ / 1 h / 20 °C

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

2.2: tetrahydrofuran; hexane / -78 °C

3.1: 1.06 g / p-toluenesulfonic acid / tetrahydrofuran; H₂O / 24 h / 20 °C

4.1: 83.5 percent / NaH; n-BuLi / tetrahydrofuran; hexane / 3 h / -10 °C

With n-butyllithium; sodium acetate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; water;

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

upstream raw materials:

ethyl acetoacetate

(E)-3-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-propenal

2-amino-4'-fluorobenzophenone

methyl 3-cyclopropyl-3-oxopropanoate

Downstream raw materials:

(±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester

ethyl (E)-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]hept-6-enoate

(E)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dioxo-hept-6-enoic acid ethyl ester

pitavastatin