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125971-96-2

Basic Information
CAS No.: 125971-96-2
Name: 4-Fluoro-alpha-(2-methyl-1-oxopropyl)-gamma-oxo-N,bata-diphenylbenzene butaneamide
Article Data: 22
Cas Database
Molecular Structure:
Molecular Structure of 125971-96-2 (4-Fluoro-alpha-(2-methyl-1-oxopropyl)-gamma-oxo-N,bata-diphenylbenzene butaneamide)
Formula: C26H24FNO3
Molecular Weight: 417.48
Synonyms: 2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoicacid phenylamide;
EINECS: 425-850-3
Density: 1.212 g/cm3
Melting Point: 196-198 °C
Boiling Point: 631.4 °C at 760 mmHg
Flash Point: 335.6 °C
Solubility: N/A
Appearance: white to off-white solid
Hazard Symbols: N/A
Risk Codes: N/A
Safety:
Transport Information: N/A
PSA: 63.24000
LogP: 5.34520
Synthetic route
7342-02-1

3-phenylpropynoic acid phenylamide

459-57-4

4-fluorobenzaldehyde

78-84-2

isobutyraldehyde

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With copper(II) hexafluoroantimonate; C32H44Cl2N4O6Pd In tetrahydrofuran at 50 - 60℃; for 24h; Solvent; Reagent/catalyst; Inert atmosphere;87.5%
62148-67-8

2-chloro-1-(4-fluorophenyl)-2-phenylethan-1-one

124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With potassium carbonate In acetone at 25 - 60℃; Reflux;74%
88675-31-4

2-bromo-1-(4-fluorophenyl)-2-phenylethan-1-one

124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

A

347-84-2

1-(4-fluorophenyl)-2-phenylethanone

B

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 5h; Reagent/catalyst; Time; Darkness;A n/a
B 80%
124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With potassium carbonate In isopropyl alcohol at 10 - 45℃; Product distribution / selectivity;73%
Multi-step reaction with 2 steps
1: β-alanine; glacial acetic acid / hexane / Heating
2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; 4-amino-phenol / hexane / 24 h / Reflux
2.1: triethylamine; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / neat (no solvent) / 16 h / 75 °C / Inert atmosphere
2.2: 4 h / 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: glycine; acetic acid / n-heptane / 8 h / Inert atmosphere; Reflux
2: 10 h / 20 °C / Inert atmosphere
View Scheme

2-benzylidine isobutyryl acetanilide

459-57-4

4-fluorobenzaldehyde

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With triethylamine; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide In tetrahydrofuran at 60 - 70℃; for 16 - 24h; Stetter reaction;
459-57-4

4-fluorobenzaldehyde

125971-57-5

4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
Stage #1: 4-fluorobenzaldehyde; 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In neat (no solvent) at 75℃; for 16h; Inert atmosphere;
Stage #2: With isopropyl alcohol at 25℃; for 4h; Inert atmosphere;
85%
With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In ethanol Addition; Heating;
at 20℃; for 10h; Inert atmosphere;33 g
With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine Stetter 1,4-Dicarbonyl Synthesis; Reflux;
807361-46-2

2-bromo-4-methyl-3-oxo-pentanoic acid phenylamide

347-84-2

1-(4-fluorophenyl)-2-phenylethanone

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -25 - -10℃; for 0.5h;
Stage #2: 1-(4-fluorophenyl)-2-phenylethanone In tetrahydrofuran; hexane at -78 - -60℃; for 1h;
Stage #3: 2-bromo-4-methyl-3-oxo-pentanoic acid phenylamide In tetrahydrofuran; hexane at -78 - 15℃; for 1.5h;
85%
Stage #1: 1-(4-fluorophenyl)-2-phenylethanone With sodium carbonate In N,N-dimethyl-formamide for 0.25h;
Stage #2: 2-bromo-4-methyl-3-oxo-pentanoic acid phenylamide In N,N-dimethyl-formamide at 90℃; for 23h; Product distribution / selectivity;
Stage #1: 1-(4-fluorophenyl)-2-phenylethanone With sodium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.5h;
Stage #2: 2-bromo-4-methyl-3-oxo-pentanoic acid phenylamide In N,N-dimethyl-formamide at 20 - 95℃; for 29.17h; Product distribution / selectivity;
88675-31-4

2-bromo-1-(4-fluorophenyl)-2-phenylethan-1-one

124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Reflux;78%
With potassium carbonate In acetone at 18.5 - 26℃; Product distribution / selectivity;77.7%
With potassium carbonate In acetone at 18 - 26℃;74%

2-[2,2-bis-ethylsulphanyl-2-(4-fluoro-phenyl)-1-phenyl-ethyl]-4-methyl-3-oxo-pentanoic acid phenylamide

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water; mercury(II) oxide In tetrahydrofuran for 0.5h;49%

2-{[2-(4-fluoro-phenyl)-[1,3]dithian-2-yl]-phenyl-methyl}-4-methyl-3-oxo-pentanoic acid phenylamide

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions
ConditionsYield
With water; copper(II) oxide; copper dichloride In acetone for 1h; Heating / reflux;54%
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Chemistry

Molecule structure of 2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide (CAS NO.125971-96-2):

Molecular Weight: 417.4721 g/mol
Molecular Formula: C26H24FNO3 
Density: 1.212 g/cm3 
Melting Point: 196-198 °C
Boiling Point: 631.378 °C at 760 mmHg 
Flash Point: 335.645 °C
Index of Refraction: 1.599
Molar Refractivity: 117.719 cm3
Molar Volume: 344.504 cm3 
Surface Tension: 48.304 dyne/cm 
Enthalpy of Vaporization: 93.37 kJ/mol 
InChI: InChI=1/C26H24FNO3/c1-17(2)24(29)23(26(31)28-21-11-7-4-8-12-21)22(18-9-5-3-6-10-18)25(30)19-13-15-20(27)16-14-19/h3-17,22-23H,1-2H3,(H,28,31) 
InChIKey: SNPBHOICIJUUFB-UHFFFAOYAO 
Product Categories: Chemical intermediate for Atorvastatin Calcium; INTERMEDIATESOFATORVASTATIN; (intermediate of atorvastatin); Aromatices; Intermediates & Fine Chemicals; Pharmaceuticals

Uses

 2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide (CAS NO.125971-96-2) is used as an atorvastatin intermediate. Atorvastatin is a selective, competitive HMG-CoA reductase inhibitor. The only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.

Specification

 2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide (CAS NO.125971-96-2) is also named as 4-Fluoro-alpha-(2-methyl-1-oxopropyl)-gamma-oxo-N,beta-diphenylbenzenebutanamide ; benzenebutanamide, 4-fluoro-alpha-(2-methyl-1-oxopropyl)-gamma-oxo-N,beta-diphenyl- ; 4-Fluoro-Alpha-(2-Methyl-1-Oxopropyl)-Gamma-Oxo-N,Beta-Diphenylbenzene Butaneamide .  2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide (CAS NO.125971-96-2) is white to off-white solid.