N-{4-hydroxy-3-[(2E)-3-phenylprop-2-enoyl]phenyl}acetamide

Base Information

• Chemical Name: N-{4-hydroxy-3-[(2E)-3-phenylprop-2-enoyl]phenyl}acetamide
• CAS No.: 24449-58-9
• Molecular Formula: C17H15 N O3
• Molecular Weight: 281.311
• Hs Code.: 2924299090
• European Community (EC) Number: 246-266-3
• ChEMBL ID: CHEMBL164129
• Nikkaji Number: J287.259E
• Mol file: 24449-58-9.mol

Synonyms:N-[4-HYDROXY-3-(1-OXO-3-PHENYLALLYL)PHENYL]ACETAMIDE;CHEMBL164129;SCHEMBL5130616;N-[4-hydroxy-3-[(E)-3-phenylprop-2-enoyl]phenyl]acetamide;N-{4-hydroxy-3-[(2E)-3-phenylprop-2-enoyl]phenyl}acetamide;AKOS005177061;NS00049907;(E)-N-(3-Cinnamoyl-4-hydroxyphenyl) acetamine

Chemical Property of N-{4-hydroxy-3-[(2E)-3-phenylprop-2-enoyl]phenyl}acetamide

Chemical Property:

• Vapor Pressure: 8.09E-13mmHg at 25°C
• Boiling Point: 552.6°Cat760mmHg
• Flash Point: 288°C
• PSA: 69.89000
• Density: 1.27g/cm³
• LogP: 3.89620
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 281.10519334
• Heavy Atom Count: 21
• Complexity: 399

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1=CC(=C(C=C1)O)C(=O)C=CC2=CC=CC=C2
• Isomeric SMILES: CC(=O)NC1=CC(=C(C=C1)O)C(=O)/C=C/C2=CC=CC=C2

Technology Process of N-{4-hydroxy-3-[(2E)-3-phenylprop-2-enoyl]phenyl}acetamide

There total 3 articles about N-{4-hydroxy-3-[(2E)-3-phenylprop-2-enoyl]phenyl}acetamide 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: 85.16%

5-acetamido-2-hydroxyacetophenone (7298-67-1) + benzaldehyde (100-52-7) → 5′-acetamino-2′-hydroxychalcone (24449-58-9)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 30 ℃; for 12h;

DOI:10.1248/cpb.c15-00454

Reference yield:

4-acetaminophenol (103-90-2,8055-08-1) → 5′-acetamino-2′-hydroxychalcone (24449-58-9)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum (III) chloride / nitrobenzene / Reflux

2: potassium hydroxide / ethanol / 12 h / 30 °C

With aluminum (III) chloride; potassium hydroxide; In ethanol; nitrobenzene;

DOI:10.1007/s00044-013-0486-7

Reference yield:

→ 5′-acetamino-2′-hydroxychalcone (24449-58-9)

Guidance literature:

2-Hydroxy-5-acetamidoacetophenon, PhCHO-NaOH;

upstream raw materials:

5-acetamido-2-hydroxyacetophenone

benzaldehyde

4-acetaminophenol

Downstream raw materials:

acetic acid-[3-(2,3-dibromo-3-phenyl-propionyl)-4-hydroxy-anilide]

4-benzylidene-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one

4-(4-methoxybenzylidene)-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one

4-(3,4-dichlorobenzylidene)-1-(4-oxo-2-phenyl-4H-chromen-6-yl)-2-phenyl-1H-imidazol-5-one

Refernces

• 1、 Moorkoth, Sudheer,Srinivasan,Gopalan Kutty,Joseph, Alex,Naseer. "Synthesis and evaluation of a series of novel imidazolidinone analogues of 6-aminoflavone as anticancer and anti-inflammatory agents". . p. 5066 - 5075. Retrieved 2013/09/23.
• 2、 Casano, Gilles,Robin, Maxime,Barbier, Pascale,Peyrotb, Vincent,Faurea, Robert. "Synthesis and complete assignment of the 1H and 13C NMR signals of new acetamido and aminoflavonoid derivatives". experimental part. p. 738 - 744. Retrieved 2011/05/02.