Methylliderone

Base Information

• Chemical Name: Methylliderone
• CAS No.: 3984-73-4
• Molecular Formula: C17H16O5
• Molecular Weight: 300.311
• Hs Code.: 2914190090
• UNII: YYE85YM58K
• DSSTox Substance ID: DTXSID301045474
• Nikkaji Number: J1.563.501K,J968.844G
• Wikidata: Q15634228
• Metabolomics Workbench ID: 26913
• ChEMBL ID: CHEMBL44725
• Mol file: 3984-73-4.mol

Synonyms:Methylliderone;methyl linderone;YYE85YM58K;CHEMBL44725;4,5-Dimethoxy-2-((2E)-1-methoxy-3-phenyl-2-propen-1-ylidene)-4-cyclopentene-1,3-dione;4-Cyclopentene-1,3-dione, 4,5-dimethoxy-2-((2E)-1-methoxy-3-phenyl-2-propenylidene)-;4-Cyclopentene-1,3-dione, 4,5-dimethoxy-2-(1-methoxy-3-phenyl-2-propen-1-ylidene)-;4-Cyclopentene-1,3-dione, 4,5-dimethoxy-2-(1-methoxy-3-phenyl-2-propenylidene)-, (E)-;UNII-YYE85YM58K;SCHEMBL6845899;DTXSID301045474;BDBM50101140;LMPK12120438;AKOS040760556;FS-9862;Q15634228;4,5-Dimethoxy-2-(1-methoxy-3-phenylallylidine)cyclcopent-4-ene-1,3-dione;4-Cyclopentene-1,3-dione, 4,5-dimethoxy-2-(alpha-methoxycinnamylidene)-;2-(1-Methoxy-3-phenyl-2-propenylidene)-4,5-dimethoxy-4-cyclopentene-1,3-dione;4,5-Dimethoxy-2-((E)-1-methoxy-3-phenyl-allylidene)-cyclopent-4-ene-1,3-dione;4-CYCLOPENTENE-1,3-DIONE, 4,5-DIMETHOXY-2-(.ALPHA.-METHOXYCINNAMYLIDENE)-;2699712-20-2

Chemical Property of Methylliderone

Chemical Property:

• Melting Point: 83-85 °C
• Boiling Point: 570.1±50.0 °C(Predicted)
• PSA: 61.83000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 2.25650
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 300.09977361
• Heavy Atom Count: 22
• Complexity: 519

Purity/Quality:

98%min ^*data from raw suppliers

Tridec-5-en-3-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=O)C(=C(C=CC2=CC=CC=C2)OC)C1=O)OC
• Isomeric SMILES: COC1=C(C(=O)C(=C(/C=C/C2=CC=CC=C2)OC)C1=O)OC

Technology Process of Methylliderone

There total 15 articles about Methylliderone 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%

Linderone (93012-70-5) → Methyllinderone (3984-73-4)

Guidance literature:

With potassium carbonate; dimethyl sulfate; In acetone; Reflux;

DOI:10.3390/molecules23071521

Reference yield: 90.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Linderone (93012-70-5) → Methyllinderone (3984-73-4)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; diethyl ether; water; at 70 ℃; for 1h;

DOI:10.1021/ol200418e

Reference yield: 72.0%

sodium methylate (124-41-4) + 2-((E)-1-Bromo-3-phenyl-allylidene)-4,5-dimethoxy-cyclopent-4-ene-1,3-dione (361147-57-1) → Methyllinderone (3984-73-4)

Guidance literature:

In methanol;

DOI:10.1016/S0960-894X(01)00265-7

upstream raw materials:

sodium methylate

2-((E)-1-Bromo-3-phenyl-allylidene)-4,5-dimethoxy-cyclopent-4-ene-1,3-dione

4-hydroxy-2,3-dimethoxy-4-(4-phenyl-but-1-ynyl)-cyclobut-2-enone

2-(1-bromo-3-phenyl-propylidene)-4,5-dimethoxy-cyclopent-4-ene-1,3-dione

Downstream raw materials:

(+/-)-bi-linderone

(+/-)-linderaspirone A

linderaspirone A

bilinderone

Refernces

• 1、 Tan, Haibo,Zheng, Chao,Liu, Zheng,Wang, David Zhigang. "Biomimetic total syntheses of linderaspirone A and bi-linderone and revisions of their biosynthetic pathways". supporting information; experimental part. p. 2192 - 2195. Retrieved 2011/06/25.