2-(10-Acetoxydecyl)-3-methyl-5,6-dimethoxy-p-benzoquinone

Base Information

• Chemical Name: 2-(10-Acetoxydecyl)-3-methyl-5,6-dimethoxy-p-benzoquinone
• CAS No.: 58186-28-0
• Molecular Formula: C21H32O6
• Molecular Weight: 380.481
• DSSTox Substance ID: DTXSID101144193
• Nikkaji Number: J1.649.137C
• Mol file: 58186-28-0.mol

Synonyms:SCHEMBL7330799;SAAXJJSVGGARNN-UHFFFAOYSA-N;DTXSID101144193;2-(10-Acetoxydecyl)-3-methyl-5,6-dimethoxy-p-benzoquinone;6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone;6-(10-acetoxydecyl)-2,3-dimethoxy-5-methyl-l,4-benzoquinone;2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone;2-[10-(Acetyloxy)decyl]-5,6-dimethoxy-3-methyl-2,5-cyclohexadiene-1,4-dione;58186-28-0

Chemical Property of 2-(10-Acetoxydecyl)-3-methyl-5,6-dimethoxy-p-benzoquinone

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 14
• Exact Mass: 380.21988874
• Heavy Atom Count: 27
• Complexity: 600

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C(=C(C1=O)OC)OC)CCCCCCCCCCOC(=O)C

Technology Process of 2-(10-Acetoxydecyl)-3-methyl-5,6-dimethoxy-p-benzoquinone

There total 32 articles about 2-(10-Acetoxydecyl)-3-methyl-5,6-dimethoxy-p-benzoquinone 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: 90.7%

Idebenone (58186-27-9) + acetic anhydride (108-24-7) → 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone (58186-28-0)

Guidance literature:

With pyridine; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1246/bcsj.57.3182

Reference yield: 81.0%

6-(10-acetoxydecyl)-2,3-dimethoxy-5-methylphenol (77712-30-2) → 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone (58186-28-0)

Guidance literature:

With potassium dihydrogenphosphate; potassiuim nitrosodisulfonate; In methanol; water; N,N-dimethyl-formamide; at 5 ℃; for 72h;

DOI:10.1248/cpb.33.4422

Reference yield: 45.0%

10-(2,3,4-trimethoxy-6-methylphenyl)decyl acetate (1286209-75-3) → 2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone (58186-28-0)

Guidance literature:

With dihydrogen peroxide; toluene-4-sulfonic acid; In acetic acid; at 75 ℃; for 0.416667h;

DOI:10.1021/op200051v

upstream raw materials:

Idebenone

acetic anhydride

10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoic acid

6-(10-acetoxydecyl)-2,3-dimethoxy-5-methylphenol

Downstream raw materials:

6-(10-Acetoxydecyl)-2,3-dimethoxy-5-methylhydroquinone

Idebenone

10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>-1-decanol

10-<3,4-dimethoxy-2,5-di(methoxymethoxy)-6-methylphenyl>decanal

Refernces

• 1、 Jung,Joe,Seong,Park. "Synthesis of idebenone; a synthetic analog of coenzyme Q". . p. 2735 - 2741. Retrieved 2007/10/03.
• 2、 -. "Method of producing quinone derivatives". . . Retrieved 2008/06/13.