3-[(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-phenethyl-carbamoyl]-acrylic acid

Base Information

• Chemical Name: 3-[(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-phenethyl-carbamoyl]-acrylic acid
• CAS No.: 5567-36-2
• Molecular Formula: C22H20N2O5
• Molecular Weight: 392.4046
• DSSTox Substance ID: DTXSID10416517
• Mol file: 5567-36-2.mol

Synonyms:5567-36-2;3-[(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-phenethyl-carbamoyl]-acrylic acid;(E)-4-[(2,5-dioxo-1-phenylpyrrolidin-3-yl)-(2-phenylethyl)amino]-4-oxobut-2-enoic acid;AC1NSJIP;DTXSID10416517;KJHTUIFTMLEAMC-VAWYXSNFSA-N;STK064120;AKOS000585229;AKOS021989400;AB00089569-01;(2E)-4-[(2,5-dioxo-1-phenylpyrrolidin-3-yl)(2-phenylethyl)amino]-4-oxobut-2-enoic acid

Chemical Property of 3-[(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-phenethyl-carbamoyl]-acrylic acid

Chemical Property:

• Vapor Pressure: 3.31E-22mmHg at 25°C
• Boiling Point: 727.3°Cat760mmHg
• Flash Point: 393.7°C
• Density: 1.37g/cm³
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 392.13722174
• Heavy Atom Count: 29
• Complexity: 662

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)N(C1=O)C2=CC=CC=C2)N(CCC3=CC=CC=C3)C(=O)C=CC(=O)O
• Isomeric SMILES: C1C(C(=O)N(C1=O)C2=CC=CC=C2)N(CCC3=CC=CC=C3)C(=O)/C=C/C(=O)O

Technology Process of 3-[(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-phenethyl-carbamoyl]-acrylic acid

There total 5 articles about 3-[(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-phenethyl-carbamoyl]-acrylic acid 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: 65.0%

7-methoxy-3-(4-methoxyphenyl)-1H-isochromen-1-one (14963-91-8) → 7-hydroxy-3-(4-hydroxy-phenyl)-isochromen-1-one (5567-36-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.bmc.2005.07.014

Reference yield:

5-methoxy-2-trifluoromethanesulfonyloxy benzoic acid methyl ester (345924-12-1) → 7-hydroxy-3-(4-hydroxy-phenyl)-isochromen-1-one (5567-36-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / triethylamine; CuI; tetrabutylammonium iodide / Pd(PPh₃)4 / acetonitrile / 4 h / Heating

2: 73 percent / I₂ / acetonitrile / 2 h / 20 °C

3: 86 percent / formic acid; triethylamine; PPh₃ / Pd(OAc)2 / dimethylformamide / 60 °C

4: 65 percent / BBr₃ / CH₂Cl₂ / 24 h / 0 - 20 °C

With copper(l) iodide; formic acid; iodine; boron tribromide; tetra-(n-butyl)ammonium iodide; triethylamine; triphenylphosphine; palladium diacetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Sonogashira coupling;

DOI:10.1016/j.bmc.2005.07.014

Reference yield:

5-methoxy-2-(4-methoxyphenylethynyl)benzoic acid methyl ester (869284-18-4) → 7-hydroxy-3-(4-hydroxy-phenyl)-isochromen-1-one (5567-36-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / I₂ / acetonitrile / 2 h / 20 °C

2: 86 percent / formic acid; triethylamine; PPh₃ / Pd(OAc)2 / dimethylformamide / 60 °C

3: 65 percent / BBr₃ / CH₂Cl₂ / 24 h / 0 - 20 °C

With formic acid; iodine; boron tribromide; triethylamine; triphenylphosphine; palladium diacetate; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2005.07.014

upstream raw materials:

7-methoxy-3-(4-methoxyphenyl)-1H-isochromen-1-one

5-methoxy-2-trifluoromethanesulfonyloxy benzoic acid methyl ester

5-methoxy-2-(4-methoxyphenylethynyl)benzoic acid methyl ester

4-iodo-7-methoxy-3-(4-methoxyphenyl)isocoumarine