4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-

Base Information

• Chemical Name: 4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-
• CAS No.: 99874-36-9
• Molecular Formula: C20H20O6
• Molecular Weight: 356.375
• Mol file: 99874-36-9.mol

Synonyms:

Chemical Property of 4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-

There total 14 articles about 4H-1-Benzopyran-4-one, 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)- 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: 92.0%

5,7,4'-tris(benzyloxy)-6-(3-hydroxy-3-methyl-1-butynyl)isoflavone (844868-36-6) → 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (99874-36-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; methanol; at 20 ℃;

DOI:10.1248/cpb.52.1285

Reference yield:

4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone (67052-53-3) → 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (99874-36-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / hydrogen / palladium on carbon / methanol; ethyl acetate / 20 °C

2: 94 percent / iodine; periodic acid / ethanol / 1 h / 40 °C

3: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C

4: potassium hydroxide / ethanol / 1 h / Heating

5: 5.48 g / aq. HCl / ethanol; CHCl₃ / 1 h / 40 °C

6: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C

7: [hydroxy(tosyloxy)iodo]benzene / CHCl₃ / 24 h / 20 °C

8: 3.82 g / aq. sodium hydroxide; methanol / CHCl₃ / 5 h / 25 °C

9: 91 percent / triethylamine; PPh₃; CuI / PdCl₂ / dimethylformamide / 2 h / 80 °C

10: 88 percent / hydrogen / palladium on carbon / methanol; dioxane

With hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; copper(l) iodide; [hydroxy(tosyloxy)iodo]benzene; hydrogen; iodine; potassium carbonate; periodic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; palladium dichloride; In 1,4-dioxane; methanol; ethanol; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1080/00397910500514121

Reference yield:

2',4'-dihydroxy-3'-iodo-6'-(methoxymethoxy)acetophenone (321569-79-3) → 5,7-dihydroxy-6-(3-hydroxy-3-methylbutyl)-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (99874-36-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / potassium carbonate / dimethylformamide / 1 h / 70 °C

2: potassium hydroxide / ethanol / 1 h / Heating

3: 5.48 g / aq. HCl / ethanol; CHCl₃ / 1 h / 40 °C

4: 88 percent / potassium carbonate / dimethylformamide / 0.5 h / 60 - 70 °C

5: [hydroxy(tosyloxy)iodo]benzene / CHCl₃ / 24 h / 20 °C

6: 3.82 g / aq. sodium hydroxide; methanol / CHCl₃ / 5 h / 25 °C

7: 91 percent / triethylamine; PPh₃; CuI / PdCl₂ / dimethylformamide / 2 h / 80 °C

8: 88 percent / hydrogen / palladium on carbon / methanol; dioxane

With hydrogenchloride; methanol; potassium hydroxide; sodium hydroxide; copper(l) iodide; [hydroxy(tosyloxy)iodo]benzene; hydrogen; potassium carbonate; triethylamine; triphenylphosphine; palladium on activated charcoal; palladium dichloride; In 1,4-dioxane; methanol; ethanol; chloroform; N,N-dimethyl-formamide;

DOI:10.1080/00397910500514121

upstream raw materials:

5,7,4'-tris(benzyloxy)-6-(3-hydroxy-3-methyl-1-butynyl)isoflavone

4',6'-bis(benzyloxy)-2'-(methoxymethoxy)acetophenone

2',4'-dihydroxy-3'-iodo-6'-(methoxymethoxy)acetophenone

2',4'-bis(benzyloxy)-3'-iodo-6'-(methoxymethoxy)acetophenone

Downstream raw materials:

5,7,4'-triacetoxy-6-(3-methyl-2-butenyl)isoflavone

erythrinin B

7,4'-bis(benzoyloxy)-6-(3-hydroxy-3-methylbutyl)-5-tosyloxyisoflavone

7,4'-bis(benzoyloxy)-6-(3-methyl-2-butenyl)-5-tosyloxyisoflavone