2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide supplier

Name
2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide
EINECS 425-850-3
CAS No. 125971-96-2
Article Data22
CAS DataBase
Density 1.212 g/cm³
Solubility
Melting Point 196-198 °C
Formula C₂₆H₂₄FNO₃
Boiling Point 631.4 °C at 760 mmHg
Molecular Weight 417.48
Flash Point 335.6 °C
Transport Information
Appearance white to off-white solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoicacid phenylamide;
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

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

...Expand

: 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

Conditions	Yield
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

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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 459-57-4
4-fluorobenzaldehyde

: 54016-70-5
3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide

: 222320-29-8
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

Conditions	Yield
With triethylamine In ethanol; isopropyl alcohol
With triethylamine In ethanol; isopropyl alcohol

...Expand

: 459-57-4
4-fluorobenzaldehyde

: 54016-70-5
3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide

: 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

Conditions	Yield
With triethylamine In ethanol; isopropyl alcohol

...Expand

: 222320-17-4
4-methyl-3-oxo-N-phenyl-2-(phenylmethylene) pentanamide

: 459-57-4
4-fluorobenzaldehyde

: 54016-70-5
3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide

A (+-)4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenybenzenebutaneamide: (+-)4-fluoro-α-[2-methyl-1-oxopropyl]-γ-oxo-N,β-diphenybenzenebutaneamide

B: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
With triethylamine In ethanol

...Expand

: 459-57-4
4-fluorobenzaldehyde

: 222320-29-8
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

Conditions	Yield
With triethylamine at 65 - 70℃;	84%

: 124401-38-3
4-methyl-3-oxo-N-phenylpentanamide

A: 1198087-00-1
3-[2-(4-fluorophenyl)-2-oxo-1-phenyl-ethoxy]-4-methyl-pent-2-enoic acid phenylamide

B: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 10 - 45℃; Product distribution / selectivity;	A 14.7 %Chromat. B n/a

: 42558-54-3
Methyl 4-methyl-3-oxopentanoate

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 80 - 125 °C 2: potassium carbonate / acetone / 18.5 - 26 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / neat (no solvent) / 12 h / 135 °C 2.1: acetic acid; 4-amino-phenol / hexane / 24 h / Reflux 3.1: triethylamine; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / neat (no solvent) / 16 h / 75 °C / Inert atmosphere 3.2: 4 h / 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: ethylenediamine / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 140 - 150 °C / Inert atmosphere 2: glycine; acetic acid / n-heptane / 8 h / Inert atmosphere; Reflux 3: 10 h / 20 °C / Inert atmosphere View Scheme

: 62-53-3
aniline

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / 80 - 125 °C 2: potassium carbonate / acetone / 18.5 - 26 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / 80 - 125 °C 2: potassium carbonate / acetone / 25 - 60 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide / neat (no solvent) / 12 h / 135 °C 2.1: acetic acid; 4-amino-phenol / hexane / 24 h / Reflux 3.1: triethylamine; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / neat (no solvent) / 16 h / 75 °C / Inert atmosphere 3.2: 4 h / 25 °C / Inert atmosphere View Scheme

: 103-80-0
phenylacetyl chloride

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / -10 - 0 °C / Inert atmosphere 2: sulfuryl dichloride / dichloromethane / 10 - 20 °C 3: potassium carbonate / acetone / 25 - 60 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / -10 - 0 °C / Inert atmosphere 2: bromine; hydrogen bromide; acetic acid / dichloromethane / 26 °C 3: potassium carbonate / acetone / 18.5 - 26 °C View Scheme
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1 h / 10 °C 2.1: hydrogen bromide / water / 0.08 h / 20 °C / Darkness 2.2: 5 h / 20 °C 2.3: 12 h / 20 °C 3.1: potassium carbonate / acetone / 5 h / 20 °C / Darkness View Scheme
Multi-step reaction with 3 steps 1: zeolite / dichloromethane / 2 h / 10 °C / Cooling with ice; Molecular sieve 2: hydrogen bromide; dihydrogen peroxide; acetic acid / 16 h / 40 °C 3: potassium carbonate / acetone / 2 h / Reflux View Scheme

: 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

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuryl dichloride / dichloromethane / 10 - 20 °C 2: potassium carbonate / acetone / 25 - 60 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1: bromine; hydrogen bromide; acetic acid / dichloromethane / 26 °C 2: potassium carbonate / acetone / 18.5 - 26 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen bromide; dihydrogen peroxide; acetic acid / 16 h / 40 °C 2: potassium carbonate / acetone / 2 h / Reflux View Scheme

: 100-52-7
benzaldehyde

HI, I2: HI, I2

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
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

: 62-53-3
aniline

Wang resin-bound styrene 4: Wang resin-bound styrene 4

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / toluene / Heating 2: β-alanine; glacial acetic acid / hexane / Heating 3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating View Scheme

: isobutyryl Meldrum's acid

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / toluene / Heating 2: β-alanine; glacial acetic acid / hexane / Heating 3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating View Scheme

: 462-06-6
fluorobenzene

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / -10 - 0 °C / Inert atmosphere 2: sulfuryl dichloride / dichloromethane / 10 - 20 °C 3: potassium carbonate / acetone / 25 - 60 °C / Reflux View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / -10 - 0 °C / Inert atmosphere 2: bromine; hydrogen bromide; acetic acid / dichloromethane / 26 °C 3: potassium carbonate / acetone / 18.5 - 26 °C View Scheme

: 459-57-4
4-fluorobenzaldehyde

: 125971-57-5
4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

A

B: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
With triethylamine; ethyl thiazolium catalyst or with methyl thiazolium catalyst; 1) EtOH; Yield given. Multistep reaction;

...Expand

: fluorobenzene

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / 1 h / 10 °C 2.1: hydrogen bromide / water / 0.08 h / 20 °C / Darkness 2.2: 5 h / 20 °C 2.3: 12 h / 20 °C 3.1: potassium carbonate / acetone / 5 h / 20 °C / Darkness View Scheme

: 103-82-2
phenylacetic acid

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / chloroform / Reflux 2: zeolite / dichloromethane / 2 h / 10 °C / Cooling with ice; Molecular sieve 3: hydrogen bromide; dihydrogen peroxide; acetic acid / 16 h / 40 °C 4: potassium carbonate / acetone / 2 h / Reflux View Scheme

: 563-80-4
3-methyl-butan-2-one

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium tert-butylate / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere 2: ethylenediamine / 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 140 - 150 °C / Inert atmosphere 3: glycine; acetic acid / n-heptane / 8 h / Inert atmosphere; Reflux 4: 10 h / 20 °C / Inert atmosphere View Scheme

: 62-53-3
aniline

: 637-44-5
phenylpropyolic acid

: 125971-96-2
2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 0 - 30 °C / Large scale 2: copper(II) hexafluoroantimonate; C32H44Cl2N4O6Pd / tetrahydrofuran / 24 h / 50 - 60 °C / Inert atmosphere View Scheme

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide Chemical Properties

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

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide 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.

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide 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.

Product Name

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide

Synthetic route

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide Chemical Properties

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide Uses

2-[2-(4-Fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxo-N-phenylpentanamide Specification

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