2H-Pyran-2-one, 4-methoxy-6-(2-phenylethyl)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 4-methoxy-6-(2-phenylethyl)-
• CAS No.: 3155-51-9
• Molecular Formula: C14H14O3
• Molecular Weight: 230.263
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID10185453
• Nikkaji Number: J584.154B
• Wikidata: Q83056476
• Metabolomics Workbench ID: 125739
• ChEMBL ID: CHEMBL1946699
• Mol file: 3155-51-9.mol

Synonyms:5,6-DDK;7,8-dihydro-5,6-dehydrokawain;dihydro-5,6-dehydrokawain

Chemical Property of 2H-Pyran-2-one, 4-methoxy-6-(2-phenylethyl)-

Chemical Property:

• Vapor Pressure: 4.2E-07mmHg at 25°C
• Melting Point: 98.5 °C
• Refractive Index: 1.565
• Boiling Point: 415.2 °C at 760 mmHg
• Flash Point: 176.315 °C
• PSA: 39.44000
• Density: 1.159 g/cm³
• LogP: 2.43360
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 335

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=O)OC(=C1)CCC2=CC=CC=C2
• Uses: 4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one is a Kawain (K145490) derivative that is known to exhibit antimalarial and antituberculosis activities. 4-Methoxy-6-(2-phenylethyl)-2H-pyran-2-one has been identified as a lead compound for the dual treatment of malaria and leishmaniasis.

Technology Process of 2H-Pyran-2-one, 4-methoxy-6-(2-phenylethyl)-

There total 7 articles about 2H-Pyran-2-one, 4-methoxy-6-(2-phenylethyl)- 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%

4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one (1952-41-6,26531-51-1) → 7,8-dihydro-4-methoxy-6-styryl-2H-pyran-2-one (3155-51-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; chloroform; for 2h;

DOI:10.1016/j.bmc.2011.12.053

Reference yield:

4-methoxy-6-methyl-2H-pyran-2-one (672-89-9) → 7,8-dihydro-4-methoxy-6-styryl-2H-pyran-2-one (3155-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; magnesium / 6 h / Inert atmosphere; Reflux

2: palladium 10% on activated carbon; hydrogen / methanol; chloroform / 2 h

With methanol; palladium 10% on activated carbon; hydrogen; magnesium; In methanol; chloroform;

DOI:10.1016/j.bmc.2011.12.053

Reference yield:

benzaldehyde (100-52-7) → 7,8-dihydro-4-methoxy-6-styryl-2H-pyran-2-one (3155-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; magnesium / 6 h / Inert atmosphere; Reflux

2: palladium 10% on activated carbon; hydrogen / methanol; chloroform / 2 h

With methanol; palladium 10% on activated carbon; hydrogen; magnesium; In methanol; chloroform;

DOI:10.1016/j.bmc.2011.12.053

upstream raw materials:

diazomethane

6-phenethyl-pyran-2,4-dione

6-trans-styryl-pyran-2,4-dione

4-methoxy-6-methyl-2H-pyran-2-one

Refernces

• 1、 Israili,Smissman. "Synthesis of kavain, dihydrokavain, and analogues". . p. 4070 - 4074. Retrieved 2007/10/07.