Liquiritigenin dimethyl ether

Base Information

• Chemical Name: Liquiritigenin dimethyl ether
• CAS No.: 25826-69-1
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.312
• ChEMBL ID: CHEMBL229908
• DSSTox Substance ID: DTXSID101314100
• Nikkaji Number: J837.938F
• Wikidata: Q27163615
• Mol file: 25826-69-1.mol

Synonyms:LIQUIRITIGENIN DIMETHYL ETHER;4',7-Dimethoxyflavanone;25826-69-1;CHEMBL229908;7-methoxy-2-(4-methoxyphenyl)chroman-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-7-methoxy-2-(4-methoxyphenyl)-;7-methoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one;Spectrum_001551;SpecPlus_000343;Spectrum2_000041;Spectrum3_001724;Spectrum4_001645;Spectrum5_000489;BSPBio_003368;KBioGR_002109;KBioSS_002031;DivK1c_006439;SPECTRUM1600561;SPBio_000161;SCHEMBL3303937;SCHEMBL13394438;CHEBI:91819;KBio1_001383;KBio2_002031;KBio2_004599;KBio2_007167;KBio3_002588;7-methoxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one;DTXSID101314100;BDBM50213235;CCG-38347;SDCCGMLS-0066887.P001;NCGC00095734-01;NCGC00095734-02;SR-05000002542;SR-05000002542-1;(+/-)-7-methoxy-2-(4-methoxyphenyl)chroman-4-one;BRD-A68039575-001-02-5;Q27163615

Chemical Property of Liquiritigenin dimethyl ether

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 284.10485899
• Heavy Atom Count: 21
• Complexity: 362

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2CC(=O)C3=C(O2)C=C(C=C3)OC

Technology Process of Liquiritigenin dimethyl ether

There total 21 articles about Liquiritigenin dimethyl ether 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: 82.0%

4-methoxyphenylboronic acid (5720-07-0) + 7-methoxy-chroman-4-one (42327-52-6) → 4',7-dimethoxyflavanone (25826-69-1)

Guidance literature:

7-methoxy-chroman-4-one; With [2,2]bipyridinyl; palladium(II) trifluoroacetate; oxygen; In 1,4-dioxane; dimethyl sulfoxide; at 100 ℃; for 21h;

4-methoxyphenylboronic acid; With trifluoroacetic acid; In 1,4-dioxane; dimethyl sulfoxide; at 80 ℃; for 4h;

DOI:10.1021/acs.joc.9b01162

Reference yield: 80.0%

2'-hydroxy-4,4'-dimethoxychalcone (2198-19-8) → 4',7-dimethoxyflavanone (25826-69-1)

Guidance literature:

acid-catalyzed cyclization;

DOI:10.1016/S0040-4039(00)88565-2

Reference yield: 80.0%

2'-hydroxy-4,4'-dimethoxychalcone (2198-19-8,62881-44-1) → 4',7-dimethoxyflavanone (25826-69-1)

Guidance literature:

With pyridine; In methanol; water; for 12h; Heating;

upstream raw materials:

2'-hydroxy-4,4'-dimethoxychalcone

diazomethane

diiodomethane

2'-hydroxy-4,4'-dimethoxychalcone

Downstream raw materials:

2'-hydroxy-4,4'-dimethoxychalcone

4,7-dimethoxyflavone

4',7-Dimethoxy-flavanon-oxim-toluol-4-sulfonat

7-methoxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Refernces

• 1、 Cho, Yang Yil,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Nam Yong,Kim, Nam-Jung,Kim, Young Min,Lee, Soo Jin,Lee, Yong Sup,Park, Boyoung Y.,Son, Seung Hwan,Yoo, Hyung-Seok. "Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids". . p. 10012 - 10023. Retrieved 2019/08/30.
• 2、 Muller, Brian M.,Mai, Jesse,Yocum, Reid A.,Adler, Marc J.. "Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold". supporting information. p. 5108 - 5114. Retrieved 2014/07/08.