7,8-Dihydroyangonin

Base Information

• Chemical Name: 7,8-Dihydroyangonin
• CAS No.: 3155-52-0
• Molecular Formula: C15H16O4
• Molecular Weight: 260.29
• DSSTox Substance ID: DTXSID00433859
• Nikkaji Number: J589.562F
• Wikidata: Q82248117
• Metabolomics Workbench ID: 45854
• ChEMBL ID: CHEMBL1722569
• Mol file: 3155-52-0.mol

Synonyms:7,8-Dihydroyangonin;3155-52-0;4-methoxy-6-[2-(4-methoxyphenyl)ethyl]pyran-2-one;2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-;4-Methoxy-6-(4-methoxyphenethyl)-2H-pyran-2-one;MLS000863637;MEGxp0_001885;SCHEMBL9016228;CHEMBL1722569;ACon0_001138;ACon1_000426;DTXSID00433859;CHEBI:174417;HMS2269B09;NCGC00169091-01;SMR000440759;BRD-K45395650-001-01-7;4-methoxy-6-[2-(4-methoxyphenyl)ethyl]-2H-pyran-2-one

Chemical Property of 7,8-Dihydroyangonin

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 260.10485899
• Heavy Atom Count: 19
• Complexity: 376

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CCC2=CC(=CC(=O)O2)OC

Technology Process of 7,8-Dihydroyangonin

There total 11 articles about 7,8-Dihydroyangonin 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: 67.0%

yangonin (500-62-9) → 4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one (3155-52-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃; for 1.5h;

DOI:10.1002/ejoc.201200308

Reference yield:

4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one (1092383-57-7) → 4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one (3155-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Pd₂(dba)4; sodium acetate / 1 h / 80 °C / Microwave irradiation

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux

3: 5%-palladium/activated carbon; hydrogen / methanol / 1.5 h / 20 °C

With Pd₂(dba)4; 5%-palladium/activated carbon; hydrogen; sodium acetate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; toluene; 1: Heck-Matsuda reaction;

DOI:10.1002/ejoc.201200308

Reference yield:

4-methoxy-2-oxo-2H-pyran-6-carboxaldehyde (56070-85-0) → 4-methoxy-6-(p-methoxyphenethyl)-2H-pyran-2-one (3155-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: n-butyllithium; methyl-triphenylphosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere

2: sodium acetate; palladium diacetate / acetonitrile / 0.17 h

3: 5%-palladium/activated carbon; hydrogen / methanol / 1.5 h / 20 °C

With n-butyllithium; 5%-palladium/activated carbon; hydrogen; sodium acetate; methyl-triphenylphosphonium iodide; palladium diacetate; In tetrahydrofuran; methanol; acetonitrile; 1: Wittig reaction / 2: Heck-Matsuda reaction / 2: Heck-Matsuda reaction;

DOI:10.1002/ejoc.201200308

upstream raw materials:

diazomethane

6-(4-methoxy-phenethyl)-pyran-2,4-dione

6-(4-methoxy-trans-styryl)-pyran-2,4-dione

4-hydroxy-6-methyl-2-pyron

Refernces