4,4-dimethyl-3-oxo-N-phenylpentanamide

Base Information

• Chemical Name: 4,4-dimethyl-3-oxo-N-phenylpentanamide
• CAS No.: 61652-71-9
• Molecular Formula: C13H17NO2
• Molecular Weight: 219.283
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80356890
• Nikkaji Number: J683.927D
• Wikidata: Q82136518
• Mol file: 61652-71-9.mol

Synonyms:4,4-dimethyl-3-oxo-N-phenylpentanamide;N-PHENYL-PIVALOYLACETAMIDE;61652-71-9;SCHEMBL3937919;DTXSID80356890;STK023945;AKOS000546686;SR-01000319261;SR-01000319261-1

Chemical Property of 4,4-dimethyl-3-oxo-N-phenylpentanamide

Chemical Property:

• Melting Point: 67 °C
• Boiling Point: 388.7±25.0 °C(Predicted)
• PKA: 12.32±0.46(Predicted)
• PSA: 46.17000
• Density: 1.084±0.06 g/cm3(Predicted)
• LogP: 2.70340
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 219.125928785
• Heavy Atom Count: 16
• Complexity: 260

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)CC(=O)NC1=CC=CC=C1

Technology Process of 4,4-dimethyl-3-oxo-N-phenylpentanamide

There total 5 articles about 4,4-dimethyl-3-oxo-N-phenylpentanamide 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: 85.0%

3,3-dimethyl-butan-2-one (75-97-8) + phenyl isocyanate (103-71-9) → 4,4-dimethyl-3-oxo- N-phenylpentanamide (61652-71-9)

Guidance literature:

With lithium diisopropyl amide; In diethyl ether; 1.) -78 deg C, 15 - 20 min, 2.) -78 deg C to room temperature, 2 h;

Reference yield:

N-(4,4-dimethylpent-2-ynyl)-N-phenylhydroxylamine → 4,4-dimethyl-3-oxo- N-phenylpentanamide (61652-71-9)

Guidance literature:

With oxygen; copper(l) chloride; In tetrahydrofuran; at 40 ℃; for 5h; under 760.051 Torr;

DOI:10.1002/chem.201404201

Reference yield:

1-bromo-4,4-dimethyl-2-pentyne (52323-99-6) + N-Phenylhydroxylamine (100-65-2) → 4,4-dimethyl-3-oxo- N-phenylpentanamide (61652-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl acetamide / 2 h / 28 °C / Inert atmosphere

2: copper(l) chloride; oxygen / tetrahydrofuran / 5 h / 40 °C / 760.05 Torr

With oxygen; potassium carbonate; copper(l) chloride; In tetrahydrofuran; N,N-dimethyl acetamide;

DOI:10.1002/chem.201404201

upstream raw materials:

ethyl pivaloylacetate

aniline

3,3-dimethyl-butan-2-one

phenyl isocyanate

Downstream raw materials:

4,4-Dimethyl-3-oxo-2-[1-oxo-2,3-diphenyl-1H-indolizin-(7E)-ylidene]-pentanoic acid phenylamide

3-(2,2-Dimethyl-propionyl)-4-hydroxy-1-phenyl-pyrrole-2,5-dione

3-Chloro-4-(2,2-dimethyl-propionyl)-1-phenyl-pyrrole-2,5-dione

2-Azido-4-tert-butyl-6-phenyl-pyrrolo[3,4-d]pyrimidine-5,7-dione

Refernces

• 1、 Russo, Alessio,Galdi, Gerardina,Croce, Gianluca,Lattanzi, Alessandra. "Highly enantioselective epoxidation catalyzed by cinchona thioureas: Synthesis of functionalized terminal epoxides bearing a quaternary stereogenic center". supporting information; experimental part. p. 6152 - 6157. Retrieved 2012/06/30.