Afrormosin

Base Information

• Chemical Name: Afrormosin
• CAS No.: 550-79-8
• Molecular Formula: C17H14 O5
• Molecular Weight: 298.295
• Hs Code.: 2914509090
• UNII: 89P1SB9FYW
• ChEMBL ID: CHEMBL464404
• DSSTox Substance ID: DTXSID90203543
• Metabolomics Workbench ID: 22238
• Nikkaji Number: J11.553C
• Wikidata: Q27105693
• Mol file: 550-79-8.mol

Synonyms:afromosin

Chemical Property of Afrormosin

Chemical Property:

• Vapor Pressure: 2.86E-11mmHg at 25°C
• Boiling Point: 516°Cat760mmHg
• Flash Point: 193.6°C
• PSA: 68.90000
• Density: 1.321g/cm³
• LogP: 3.18280
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 298.08412354
• Heavy Atom Count: 22
• Complexity: 438

Purity/Quality:

99%+, ^*data from raw suppliers

Afrormosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=COC3=CC(=C(C=C3C2=O)OC)O

Technology Process of Afrormosin

There total 10 articles about Afrormosin 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: 90.0%

1,3,5-Triazine (290-87-9) + 1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (5128-54-1) → afromosin (550-79-8)

Guidance literature:

With boron trifluoride diethyl etherate; acetic anhydride; In diethyl ether; acetic acid; Heating;

Reference yield: 76.5%

3-chloro-6-methoxy-7-hydroxy-4H-chromen-4-one + 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7) → afromosin (550-79-8)

Guidance literature:

With potassium carbonate; triphenylphosphine; palladium dichloride; In 1,4-dioxane; water; for 12h; Inert atmosphere; Reflux;

Reference yield: 69.0%

1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-methoxyphenyl)ethanone (5128-54-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → afromosin (550-79-8)

Guidance literature:

1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-methoxyphenyl)ethanone; N,N-dimethyl-formamide; With boron trifluoride diethyl etherate; trichlorophosphate; at 70 - 75 ℃; for 1h;

With water; at 90 - 95 ℃; for 0.5h;

DOI:10.1007/s10600-018-2440-x

upstream raw materials:

1,3,5-Triazine

1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-methoxyphenyl)ethanone

6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

6,7,4'-trihydroxyisoflavone

Downstream raw materials:

1-(2,4-dihydroxy-5-methoxyphenyl)-2-(4-methoxyphenyl)ethanone

2,4-Dihydroxy-5,4'-dimethoxy-benzil

7-hydroxy-4',6-dimethoxyisoflavane

6-methoxy-3-(4-methoxyphenyl)4-oxo-4H-chromen-7-yl acetate

Refernces

• 1、 Bondarenko,Mrug,Kondratyuk,Frasinyuk. "Aminomethylation of Afromosin, Cladrastin, and Their 2-Methyl Derivatives". . p. 660 - 664. Retrieved 2018/08/03.
• 2、 Goto, Hideyuki,Terao, Yoshiyasu,Akai, Shuji. "Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities". experimental part. p. 346 - 360. Retrieved 2009/12/27.