2-Isobutyryl-N-phenyl-3-phenylacrylamide

Base Information

• Chemical Name: 2-Isobutyryl-N-phenyl-3-phenylacrylamide
• CAS No.: 125971-57-5
• Molecular Formula: C19H19NO2
• Molecular Weight: 293.365
• European Community (EC) Number: 425-860-8,619-636-0
• DSSTox Substance ID: DTXSID801190404
• Nikkaji Number: J1.803.451D
• Wikidata: Q76416572
• Mol file: 125971-57-5.mol

Synonyms:125971-57-5;2-ISOBUTYRYL-N-PHENYL-3-PHENYLACRYLAMIDE;(2E)-2-Benzylidene-4-methyl-3-oxo-N-phenylpentanamide;222320-17-4;265989-32-0;2-Benzylidene-4-methyl-3-oxo-N-phenylpentanamide;N-4-Phenyl alpha-Benzylidene-d5 Isobutyrylacetamide;4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide;EC 425-860-8;EC 619-636-0;SCHEMBL927020;DTXSID801190404;2-Isobutyryl-N,3-Diphenylacrylamide;AKOS015918479;A805447;(E)-N-Phenyl-4-methyl-3-oxo-2-benzylidenepentanamide;Pentanamide, 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)-;(2E)-4-Methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

Chemical Property of 2-Isobutyryl-N-phenyl-3-phenylacrylamide

Chemical Property:

• Appearance/Colour: Almost white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 143-154 °C
• Refractive Index: 1.622
• Boiling Point: 519.4ºC at 760 mmHg
• PKA: 12.23±0.70(Predicted)
• Flash Point: 188.7ºC
• PSA: 46.17000
• Density: 1.151 g/cm3
• LogP: 4.00680
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 293.141578849
• Heavy Atom Count: 22
• Complexity: 413

Purity/Quality:

99% ^*data from raw suppliers

2-Isobutyryl-N-phenyl-3-phenylacrylamide(E/Zmixture) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)C(=CC1=CC=CC=C1)C(=O)NC2=CC=CC=C2
• Isomeric SMILES: CC(C)C(=O)/C(=C\C1=CC=CC=C1)/C(=O)NC2=CC=CC=C2
• Uses: Intermediate for the synthesis of pyrrole derivatives.

Technology Process of 2-Isobutyryl-N-phenyl-3-phenylacrylamide

There total 9 articles about 2-Isobutyryl-N-phenyl-3-phenylacrylamide 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: 94.0%

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + benzaldehyde (100-52-7) → 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide (125971-57-5)

Guidance literature:

With 4-amino-phenol; acetic acid; In hexane; for 24h; Reflux;

DOI:10.1039/c5ob02546j

Reference yield:

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) + 3-amino propanoic acid (107-95-9) → 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide (125971-57-5)

Guidance literature:

With benzaldehyde; In hexane; acetic acid;

Reference yield:

Methyl 4-methyl-3-oxopentanoate (42558-54-3) → 4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide (125971-57-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / neat (no solvent) / 12 h / 135 °C

2: acetic acid; 4-amino-phenol / hexane / 24 h / Reflux

With 4-amino-phenol; acetic acid; sodium hydroxide; In hexane;

DOI:10.1039/c5ob02546j

upstream raw materials:

4-methyl-3-oxo-N-phenylpentanamide

benzaldehyde

aniline

3-amino propanoic acid

Downstream raw materials:

1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one

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

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate

Refernces

• 1、 -. "Preparation method of atorvastatin calcium". Paragraph 0016; 0017. . Retrieved 2018/07/30.
• 2、 Fleige, Mirco,Glorius, Frank. "α-Unsubstituted Pyrroles by NHC-Catalyzed Three-Component Coupling: Direct Synthesis of a Versatile Atorvastatin Derivative". supporting information. p. 10773 - 10776. Retrieved 2017/08/22.