1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

Base Information

• Chemical Name: 1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one
• CAS No.: 54299-50-2
• Molecular Formula: C₁₇H₁₆O₅
• Molecular Weight: 300.311
• DSSTox Substance ID: DTXSID60694227
• Wikidata: Q82623255
• Mol file: 54299-50-2.mol

Synonyms:1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one;2-Propen-1-one, 1-(2,4-dihydroxy-3,6-dimethoxyphenyl)-3-phenyl-,(E)-;DTXSID60694227

Chemical Property of 1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

Chemical Property:

• Vapor Pressure: 5.71E-13mmHg at 25°C
• Melting Point: 124-125°C
• Refractive Index: 1.636
• Boiling Point: 556°C at 760 mmHg
• Flash Point: 207.2°C
• PSA: 75.99000
• Density: 1.279g/cm³
• LogP: 3.01110
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 300.09977361
• Heavy Atom Count: 22
• Complexity: 389

Purity/Quality:

2'',4''-Dihydroxy-3'',6''-dimethoxychalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

There total 7 articles about 1-(2,4-Dihydroxy-3,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one 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:

2,5-dimethoxyresorcinol (20032-42-2) + cinnamoyl chloride (102-92-1,17082-09-6) → 2',4'-dihydroxy-3',6'-dimethoxychalcone (54299-50-2,129724-43-2)

Guidance literature:

2,5-dimethoxyresorcinol; cinnamoyl chloride; In chloroform; at 20 ℃; for 0.5h;

With boron trifluoride diethyl etherate; In chloroform; Reflux;

DOI:10.1016/j.bmcl.2016.12.076

Reference yield:

2-hydroxyresorcinol (87-66-1) → 2',4'-dihydroxy-3',6'-dimethoxychalcone (54299-50-2,129724-43-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: potassium iodide; potassium carbonate / acetone / 48 h / Reflux

2.1: nitric acid / acetic acid / 4 h / 40 °C

3.1: sodium dithionite / water; ethyl acetate / 1 h / 20 °C

4.1: ethanol / 0.17 h

4.2: 0.5 h / 20 °C

5.1: hydrogen; palladium 10% on activated carbon / methanol / 8 h / 20 °C

6.1: chloroform / 0.5 h / 20 °C

6.2: Reflux

With sodium dithionite; palladium 10% on activated carbon; hydrogen; nitric acid; potassium carbonate; potassium iodide; In methanol; ethanol; chloroform; water; acetic acid; ethyl acetate; acetone; 6.1: |Friedel-Crafts Acylation;

DOI:10.1016/j.bmcl.2016.12.076

Reference yield:

1,2,3-tris-benzyloxybenzene (55020-64-9) → 2',4'-dihydroxy-3',6'-dimethoxychalcone (54299-50-2,129724-43-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: nitric acid / acetic acid / 4 h / 40 °C

2.1: sodium dithionite / water; ethyl acetate / 1 h / 20 °C

3.1: ethanol / 0.17 h

3.2: 0.5 h / 20 °C

4.1: hydrogen; palladium 10% on activated carbon / methanol / 8 h / 20 °C

5.1: chloroform / 0.5 h / 20 °C

5.2: Reflux

With sodium dithionite; palladium 10% on activated carbon; hydrogen; nitric acid; In methanol; ethanol; chloroform; water; acetic acid; ethyl acetate; 5.1: |Friedel-Crafts Acylation;

DOI:10.1016/j.bmcl.2016.12.076

upstream raw materials:

2,5-dimethoxyresorcinol

2-hydroxyresorcinol

1,2,3-tris-benzyloxybenzene

2,6-bis-benzyloxy-[1,4]benzoquinone

Downstream raw materials:

(-)-celosine

(+)-celosine

7-hydroxy-5,8-dimethoxyflavone

wogonin

Refernces

• 1、 Bian, Jinlei,Li, Tinghan,Weng, Tianwei,Wang, Jubo,Chen, Yu,Li, Zhiyu. "Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents". . p. 1012 - 1016. Retrieved 2017/09/30.