ethyl trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylate

Base Information

• Chemical Name: ethyl trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylate
• CAS No.: 42059-71-2
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.247
• ChEMBL ID: CHEMBL234848
• DSSTox Substance ID: DTXSID301211489
• Nikkaji Number: J2.557.257B,J2.460.367I
• Mol file: 42059-71-2.mol

Synonyms:CHEMBL234848;DTXSID301211489;42059-71-2;ethyl trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylate;Ethyl (2E)-3-(4-oxo-4H-1-benzopyran-3-yl)-2-propenoate

Chemical Property of ethyl trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 244.07355886
• Heavy Atom Count: 18
• Complexity: 395

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=CC1=COC2=CC=CC=C2C1=O
• Isomeric SMILES: CCOC(=O)/C=C/C1=COC2=CC=CC=C2C1=O

Technology Process of ethyl trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylate

There total 3 articles about ethyl trans-3-(4-oxo-4H-1-benzopyran-3-yl)-acrylate 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: 47.0%

3-bromo-4H-chromen-4-one (49619-82-1) + ethyl acrylate (140-88-5,9003-32-1) → diethyl 2'-hydroxybenzophenone-3,5-dicarboxylate (1260485-29-7) + (2E)-3-(4-oxo-4H-chromen-3-yl)acrylic acid ethyl ester (42059-71-2)

Guidance literature:

With potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 100 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1071/CH10295

Reference yield:

1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone (106129-86-6,1776-08-5) → diethyl 2'-hydroxybenzophenone-3,5-dicarboxylate (1260485-29-7) + (2E)-3-(4-oxo-4H-chromen-3-yl)acrylic acid ethyl ester (42059-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / chloroform / 0 - 20 °C

2: potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate / 1-methyl-pyrrolidin-2-one / 0.5 h / 100 °C / Inert atmosphere

With potassium chloride; tetrabutylammomium bromide; bromine; palladium diacetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; chloroform; 2: Heck reaction;

DOI:10.1071/CH10295

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → diethyl 2'-hydroxybenzophenone-3,5-dicarboxylate (1260485-29-7) + (2E)-3-(4-oxo-4H-chromen-3-yl)acrylic acid ethyl ester (42059-71-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl-formamide / N,N-dimethyl acetamide / 100 °C

2: bromine / chloroform / 0 - 20 °C

3: potassium chloride; tetrabutylammomium bromide; palladium diacetate; potassium carbonate / 1-methyl-pyrrolidin-2-one / 0.5 h / 100 °C / Inert atmosphere

With potassium chloride; tetrabutylammomium bromide; bromine; palladium diacetate; potassium carbonate; N,N-dimethyl-formamide; In 1-methyl-pyrrolidin-2-one; chloroform; N,N-dimethyl acetamide; 3: Heck reaction;

DOI:10.1071/CH10295

upstream raw materials:

3-bromo-4H-chromen-4-one

ethyl acrylate

1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone

o-hydroxyacetophenone

Downstream raw materials:

3-(2-hydroxy-benzoyl)-9H-fluorene-1-carboxylic acid ethyl ester

3-(2-hydroxy-benzoyl)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid ethyl ester

5-(2-hydroxy-benzoyl)-biphenyl-3-carboxylic acid ethyl ester

2-(2-hydroxy-benzoyl)-9H-fluorene-4-carboxylic acid ethyl ester

Refernces