Metochalcone

Base Information

• Chemical Name: Metochalcone
• CAS No.: 30925-62-3
• Molecular Formula: C18H18O4
• Molecular Weight: 298.339
• European Community (EC) Number: 242-377-6
• NSC Number: 97905
• UNII: 1754ZE4075
• Nikkaji Number: J1.739.120H,J11.009D
• Wikidata: Q27251868
• NCI Thesaurus Code: C66129
• ChEMBL ID: CHEMBL36584
• Mol file: 30925-62-3.mol

Synonyms:1314 CB;4-methoxyphenyl- 3-(2,4-dimethoxyphenyl)-1-oxo-2-propene;metochalcone;trimethoxychalcone

Chemical Property of Metochalcone

Chemical Property:

• Melting Point: 84 °C (acetone)
• PSA: 44.76000
• LogP: 3.60850
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 298.12050905
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Metochalcone

There total 10 articles about Metochalcone 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: 97.0%

4-methoxy-benzaldehyde (123-11-5) + 2',4'-dimethoxyacetophenone (829-20-9) → metochalcone (30925-62-3)

Guidance literature:

With 4 A molecular sieve; NAP-MgO; In toluene; for 20h; Heating;

DOI:10.1021/ja038954n

Reference yield: 95.0%

para-iodoanisole (696-62-8) + 1-(2,4-dimethoxy-phenyl)-prop-2-en-1-one (67756-04-1) → metochalcone (30925-62-3)

Guidance literature:

With triethylamine; triphenylphosphine; palladium diacetate; In acetonitrile; at 85 ℃; for 5h;

DOI:10.1002/ejoc.200400032

Reference yield: 85.0%

(E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) + 1,3-Dimethoxybenzene (151-10-0) → metochalcone (30925-62-3)

Guidance literature:

(E)-3-(4-methoxyphenyl)acrylic acid; With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2h;

1,3-Dimethoxybenzene; With aluminum (III) chloride; In diethyl ether; at 20 ℃; Cooling with ice;

upstream raw materials:

4-methoxy-benzaldehyde

2',4'-dimethoxyacetophenone

isoliquirtigenin

methyl iodide

Downstream raw materials:

isoliquirtigenin

2'-hydroxy-3'-prenyl-4,4'-dimethoxychalcone

2'-hydroxy-4,4'-dimethoxychalcone

2'-hydroxy-5'-prenyl-4,4'-dimethoxychalcone

Refernces

• 1、 Ruparelia, Ketan C.,Zeka, Keti,Ijaz, Taeeba,Ankrett, Dyan N.,Wilsher, Nicola E.,Butler, Paul C.,Tan, Hoon L.,Lodhi, Sabahat,Bhambra, Avninder S.,Potter, Gerard A.,Arroo, Randolph R.J.,Beresford, Kenneth J.M.. "The synthesis of chalcones as anticancer prodrugs and their bioactivation in CYP1 expressing breast cancer cells". . p. 322 - 332. Retrieved 2018/06/26.
• 2、 -. "METHOD FOR PRODUCING LIQUIRITIGENIN PRECURSOR". Paragraph 0012; 0013. . Retrieved 2018/03/09.