(E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Base Information

• Chemical Name: (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• CAS No.: 1443276-31-0
• Molecular Formula: C₃₅H₃₈O₇
• Molecular Weight: 570.683
• Mol file: 1443276-31-0.mol

Synonyms:(E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Chemical Property of (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

There total 9 articles about (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-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: 84.0%

(E)-5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (1443276-28-5) + p-methoxybenzyl chloride (824-94-2) → (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (1443276-31-0)

Guidance literature:

(E)-5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tet.2013.05.024

Reference yield:

1-(2,4,6-trimethoxyphenyl)ethanone (832-58-6) → (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (1443276-31-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: aluminum (III) chloride / dichloromethane / 24 h / 0 °C / Reflux

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C

2.2: 0.5 h / Reflux

3.1: sodium hydride / tetrahydrofuran / 1.67 h / 0 °C / Reflux

4.1: potassium carbonate / acetone / 0.5 h

4.2: 24 h / Reflux

5.1: sulfuric acid / acetic acid / 0.5 h / 20 °C

6.1: methanol; sodium tetrahydroborate / 0.5 h

7.1: sulfuric acid / 3 h / Reflux

8.1: ethanethiol; n-butyllithium / N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / 0 - 70 °C / Inert atmosphere

9.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C

9.2: 2 h / 0 - 20 °C

With methanol; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; sulfuric acid; sodium hydride; potassium carbonate; ethanethiol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetone; 3.1: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.tet.2013.05.024

Reference yield:

2-acetyl-3,5-dimethoxy-6-(3-methylbutanoyl)phenyl 2,4-dimethoxybenzoate (1443276-19-4) → (E)-5-hydroxy-7-methoxy-2-(2-methoxy-4-((4-methoxybenzyl)oxy)phenyl)-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (1443276-31-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran / 1.67 h / 0 °C / Reflux

2.1: potassium carbonate / acetone / 0.5 h

2.2: 24 h / Reflux

3.1: sulfuric acid / acetic acid / 0.5 h / 20 °C

4.1: methanol; sodium tetrahydroborate / 0.5 h

5.1: sulfuric acid / 3 h / Reflux

6.1: ethanethiol; n-butyllithium / N,N,N,N,N,N-hexamethylphosphoric triamide / 2 h / 0 - 70 °C / Inert atmosphere

7.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C

7.2: 2 h / 0 - 20 °C

With methanol; sodium tetrahydroborate; n-butyllithium; sulfuric acid; sodium hydride; potassium carbonate; ethanethiol; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; acetic acid; N,N-dimethyl-formamide; acetone; 1.1: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.tet.2013.05.024

upstream raw materials:

(E)-5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

p-methoxybenzyl chloride

1-(2,4,6-trimethoxyphenyl)ethanone

1-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-3-methyl-1-butanone

Downstream raw materials:

(E)-5-hydroxy-2-(4-hydroxy-2-methoxyphenyl)-7-methoxy-6-(3-methylbut-1-en-1-yl)-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Artocarpin