(2E)-2-benzylidene-1-benzofuran-3-one

Base Information

• Chemical Name: (2E)-2-benzylidene-1-benzofuran-3-one
• CAS No.: 582-04-7
• Molecular Formula: C₁₅H₁₀O₂
• Molecular Weight: 222.243
• UNII: P3PDY72JP9
• Mol file: 582-04-7.mol

Synonyms:(2E)-2-benzylidene-1-benzofuran-3-one;2-benzylidene-1-benzofuran-3(2H)-one;P3PDY72JP9;SCHEMBL13971324;3(2H)-Benzofuranone, 2-benzylidene-;2-(Phenylmethylene)-3(2H)-benzofuranone;2-Benzylidene-2,3-dihydrobenzofuran-3-one;3(2H)-Benzofuranone, 2-(phenylmethylene)-;(2E)-2-(Phenylmethylene)-3(2H)-benzofuranone;AH-232/02736038;3(2H)-Benzofuranone, 2-(phenylmethylene)-, (2E)-

Chemical Property of (2E)-2-benzylidene-1-benzofuran-3-one

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 222.068079557
• Heavy Atom Count: 17
• Complexity: 326

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C2C(=O)C3=CC=CC=C3O2
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/2\C(=O)C3=CC=CC=C3O2

Technology Process of (2E)-2-benzylidene-1-benzofuran-3-one

There total 40 articles about (2E)-2-benzylidene-1-benzofuran-3-one 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: 75.0%

1-(o-hydroxyphenyl)-3-phenylpropargylic alcohol (109365-86-8) → FLAVONE (525-82-6,66585-04-4) + aurone (582-04-7,37542-14-6,75318-34-2)

Guidance literature:

With lithium tert-butoxide; In N,N-dimethyl-formamide; at 20 - 60 ℃; for 2h; Reagent/catalyst; Solvent; regioselective reaction;

DOI:10.1002/ejoc.201201665

Reference yield: 74.0%

1-(2-acetoxy-phenyl)-3-phenyl-2-propyn-1-one (16619-67-3) → FLAVONE (525-82-6,66585-04-4) + aurone (582-04-7,37542-14-6,75318-34-2)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1002/ejoc.201200529

Reference yield: 59.9%

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one (16619-68-4) → FLAVONE (525-82-6,66585-04-4) + aurone (582-04-7,37542-14-6,75318-34-2)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

upstream raw materials:

3-oxo-2,3-dihydrobenzo[b]furan

benzaldehyde

(E)-2'-hydroxy-chalcone

1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one

Downstream raw materials:

benzoic acid

2-benzylbenzofuran

3-(2-hydroxyphenyl)-1-phenyl-1-propene

trans-2-benzylidene-2H-benzofuran-3-one epoxide

Refernces

Synthesis, biological evaluation, and molecular simulation of chalcones and aurones as selective MAO-B inhibitors

10.1111/cbdd.12458

The research study on the synthesis, biological evaluation, and molecular simulation of chalcones and aurones as selective monoamine oxidase-B (MAO-B) inhibitors. The purpose of the study was to explore the potential of these compounds as therapeutic agents, particularly for neuropsychiatric and neurodegenerative disorders, by assessing their ability to inhibit the B isoform of MAO in the micromolar range. The researchers synthesized a series of chalcones and aurones and evaluated their inhibitory activity against MAO-A and MAO-B using rat brain mitochondrial suspension and selective substrates. The results indicated that both chalcones and aurones selectively inhibited MAO-B, with chalcones generally showing higher activity than aurones.

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