5-Hydroxy-2-methoxy-1,4-naphthoquinone

Base Information

• Chemical Name: 5-Hydroxy-2-methoxy-1,4-naphthoquinone
• CAS No.: 15127-94-3
• Molecular Formula: C11H8O4
• DSSTox Substance ID: DTXSID20435638
• Nikkaji Number: J958.549D
• Wikidata: Q82250687
• Metabolomics Workbench ID: 137974
• ChEMBL ID: CHEMBL480099
• Mol file: 15127-94-3.mol

Synonyms:2-methoxyjuglone

Chemical Property of 5-Hydroxy-2-methoxy-1,4-naphthoquinone

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 204.04225873
• Heavy Atom Count: 15
• Complexity: 332

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=O)C2=C(C1=O)C=CC=C2O

Technology Process of 5-Hydroxy-2-methoxy-1,4-naphthoquinone

There total 11 articles about 5-Hydroxy-2-methoxy-1,4-naphthoquinone 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: 85.0%

methanol (67-56-1) + 5-hydroxynaphtho-1,4-quinone (481-39-0) → 8-hydroxy-2-methoxynaphthalene-1,4-dione (15254-76-9) + 2-methoxy-5-hydroxy-1,4-naphthoquinone (15127-94-3)

Guidance literature:

With iron(III) sulfate; sulfuric acid; for 2h; Yields of byproduct given; Heating;

DOI:10.1002/ardp.19893220308

Reference yield: 83.0%

2-methoxy-1,4-naphthoquinone (2348-82-5) → 2-methoxy-5-hydroxy-1,4-naphthoquinone (15127-94-3) + 5,8-dihydroxy-2-methoxy-[1,4]naphthoquinone (14918-66-2)

Guidance literature:

With Ru(CF₃CO₂)2(p-cymene)(H₂O); bis-[(trifluoroacetoxy)iodo]benzene; In trifluoroacetic acid; trifluoroacetic anhydride; at 80 ℃; for 12h;

DOI:10.1021/acs.orglett.5b01138

Reference yield:

2-hydroxynaphtho-1,4-quinone (83-72-7) → 2-methoxy-5-hydroxy-1,4-naphthoquinone (15127-94-3) + 5,8-dihydroxy-2-methoxy-[1,4]naphthoquinone (14918-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 14 h / 65 °C

2: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; bis-[(trifluoroacetoxy)iodo]benzene; trifluoroacetic anhydride; trifluoroacetic acid / 12 h / 80 °C / Sealed tube

With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; sulfuric acid; trifluoroacetic acid; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene;

DOI:10.1039/c8cc07572g

upstream raw materials:

methanol

5-hydroxynaphtho-1,4-quinone

3-chlorojuglone

3-Bromojuglone

Downstream raw materials:

3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone

2-Hydroxyjuglon

Refernces

• 1、 Dias, Gleiston G.,Rogge, Torben,Kuniyil, Rositha,Jacob, Claus,Menna-Barreto, Rubem F. S.,Da Silva Júnior, Eufranio N.,Ackermann, Lutz. "Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents". supporting information. p. 12840 - 12843. Retrieved 2018/11/30.
• 2、 Wurm,Geres. "1,4-Naphthoquinones, XVII: Studies on the synthesis of 3-hydroxy-juglone derivatives". . p. 155 - 157. Retrieved 2007/10/02.