1,4-Naphthalenedione, 5,6-dihydroxy-3-methoxy-2-methyl-

Base Information

• Chemical Name: 1,4-Naphthalenedione, 5,6-dihydroxy-3-methoxy-2-methyl-
• CAS No.: 915764-62-4
• Molecular Formula: C₁₂H₁₀O₅
• Molecular Weight: 234.208
• Mol file: 915764-62-4.mol

Synonyms:1,4-Naphthalenedione,5,6-dihydroxy-3-methoxy-2-methyl;

Chemical Property of 1,4-Naphthalenedione, 5,6-dihydroxy-3-methoxy-2-methyl-

Chemical Property:

• PSA: 83.83000
• LogP: 1.19340

Purity/Quality:

99% ^*data from raw suppliers

MalvoneA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Malvone A, a phytoalexin found in Malva sylvestris, is shown to have antimicrobial and antiinflammatory acitivies.

Technology Process of 1,4-Naphthalenedione, 5,6-dihydroxy-3-methoxy-2-methyl-

There total 9 articles about 1,4-Naphthalenedione, 5,6-dihydroxy-3-methoxy-2-methyl- 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: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3,5,6-trihydroxy-2-methyl-1,4-naphthoquinone (1093228-16-0) → malvone A (915764-62-4)

Guidance literature:

In 1,4-dioxane; diethyl ether; chemoselective reaction;

DOI:10.1016/j.tetlet.2019.03.016

Reference yield:

C16H14O7 → malvone A (915764-62-4)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1055/s-0028-1088134

Reference yield:

2-hydroxy-1-methoxy-4-propionylbenzene (829-76-5) → malvone A (915764-62-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: neat (no solvent) / 4 h / 200 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.1: tetrabutylammomium bromide; sodium periodate; water / ethyl acetate / 24 h / 20 °C

5.1: hydrogenchloride; acetyl chloride / Reflux

6.1: sodium methylate / methanol / 4 h / Reflux

6.2: 12 h

7.1: ethanethiol; aluminum (III) chloride / dichloromethane / 24 h / 20 °C

8.1: diethyl ether; 1,4-dioxane

With hydrogenchloride; aluminum (III) chloride; sodium periodate; tetrabutylammomium bromide; water; sodium methylate; potassium carbonate; acetyl chloride; ethanethiol; In 1,4-dioxane; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 2.1: |Claisen Rearrangement / 6.1: |Dieckmann Condensation;

DOI:10.1016/j.tetlet.2019.03.016

upstream raw materials:

2-hydroxy-1-methoxy-4-propionylbenzene

3-allyl-1,2-dimethoxy-4-propionylbenzene

3-hydroxy-5,6-dimethoxy-2-methylnaphthalene-1,4-dione

diazomethane

Refernces

• 1、 Wu, Kun-Liang,Cohen, Elysia P. M. T.,Huang, Yaodong,Pettus, Thomas R. R.. "First total synthesis of malvone A and formal syntheses of boryquinone and hybocarpone using a concise strategy for construction of unsymmetrical naphthoquinones". experimental part. p. 1273 - 1276. Retrieved 2009/09/06.