3-(3,4-Dihydroxyphenyl)-N-phenethylpropenamide, (E)-

Base Information

• Chemical Name: 3-(3,4-Dihydroxyphenyl)-N-phenethylpropenamide, (E)-
• CAS No.: 103188-47-2
• Molecular Formula: C17H17NO3
• Molecular Weight: 283.327
• UNII: BTT4WXT3J9
• ChEMBL ID: CHEMBL67498
• DSSTox Substance ID: DTXSID101030308
• Nikkaji Number: J415.788E,J1.475.302H
• Mol file: 103188-47-2.mol

Synonyms:KS370G

Chemical Property of 3-(3,4-Dihydroxyphenyl)-N-phenethylpropenamide, (E)-

Chemical Property:

• PSA: 69.56000
• LogP: 2.86080
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 283.12084340
• Heavy Atom Count: 21
• Complexity: 350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 3-(3,4-Dihydroxyphenyl)-N-phenethylpropenamide, (E)-

There total 6 articles about 3-(3,4-Dihydroxyphenyl)-N-phenethylpropenamide, (E)- 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: 82.0%

caffeic acid (331-39-5,501-16-6) + phenethylamine (64-04-0) → (E)-3-(3,4-dihydroxyphenyl)-N-phenethyl-acrylamide (103188-47-2)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ddr.21038

Reference yield:

Acetic acid 2-acetoxy-5-((E)-2-phenethylcarbamoyl-vinyl)-phenyl ester (913283-06-4) → (E)-3-(3,4-dihydroxyphenyl)-N-phenethyl-acrylamide (103188-47-2)

Guidance literature:

With sodium carbonate; In ethanol; for 2h; Yield given; Heating;

DOI:10.1248/cpb.40.396

Reference yield:

C29H45NO3Si2 → (E)-3-(3,4-dihydroxyphenyl)-N-phenethyl-acrylamide (103188-47-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1016/j.bmc.2010.05.080

upstream raw materials:

Acetic acid 2-acetoxy-5-((E)-2-phenethylcarbamoyl-vinyl)-phenyl ester

caffeic acid

phenethylamine

3,4-diacetoxycinnamic acid

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