2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran

Base Information

• Chemical Name: 2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran
• CAS No.: 109194-69-6
• Molecular Formula: C17H14O2
• Molecular Weight: 250.297
• DSSTox Substance ID: DTXSID801253246
• Nikkaji Number: J1.163.617I,J445.355G
• Wikidata: Q27137591
• Metabolomics Workbench ID: 126955
• ChEMBL ID: CHEMBL2147422
• Mol file: 109194-69-6.mol

Synonyms:CHEMBL2147422;CHEBI:69252;2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran;DTXSID801253246;BDBM50391887;4-[5-(1-Propenyl)benzofuran-2-yl]phenol;4-[5-[(E)-1-Propenyl]benzofuran-2-yl]phenol;4-[5-(1E)-1-Propen-1-yl-2-benzofuranyl]phenol;Q27137591;4-{5-[(1E)-prop-1-en-1-yl]-1-benzofuran-2-yl}phenol;109194-69-6

Chemical Property of 2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran

Chemical Property:

• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 250.099379685
• Heavy Atom Count: 19
• Complexity: 317

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CC2=C(C=C1)OC(=C2)C3=CC=C(C=C3)O
• Isomeric SMILES: C/C=C/C1=CC2=C(C=C1)OC(=C2)C3=CC=C(C=C3)O

Technology Process of 2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran

There total 4 articles about 2-(4-hydroxyphenyl)-5-(E)-propenylbenzofuran 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: 93.0%

(E)-2-(4-(methoxymethoxy)phenyl)-5-(prop-1-en-1-yl)benzo[b]furan → 2-(4-hydroxyphenyl)-5-((E)-prop-2-en-1-yl)benzofuran (109194-69-6)

Guidance literature:

With hydrogenchloride; In methanol; water; Heating;

DOI:10.3390/biom10081131

Reference yield: 92.0%

2-(4-benzyloxyphenyl)-5-(1-propenyl)benzofuran (1254219-31-2) → 2-(4-hydroxyphenyl)-5-((E)-prop-2-en-1-yl)benzofuran (109194-69-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 20 ℃;

DOI:10.1055/s-0029-1218826

Reference yield:

5-chloro-2-(4-(methoxymethoxy)phenyl)benzo[b]furan → 2-(4-hydroxyphenyl)-5-((E)-prop-2-en-1-yl)benzofuran (109194-69-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate / 1,4-dioxane / 5 h / 100 °C / Inert atmosphere

2: bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; isobutyryl chloride / Inert atmosphere; Heating

3: hydrogenchloride / methanol; water / Heating

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; isobutyryl chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; methanol; water; 1: |Suzuki-Miyaura Coupling;

DOI:10.3390/biom10081131

upstream raw materials:

2-(4-benzyloxyphenyl)-5-(1-propenyl)benzofuran

p-methoxymethoxybromobenzene