Aurantiogliocladin

Base Information

• Chemical Name: Aurantiogliocladin
• CAS No.: 483-54-5
• Molecular Formula: C10H12O4
• Molecular Weight: 196.203
• UNII: 74R18PLB3Z
• ChEMBL ID: CHEMBL2252961
• DSSTox Substance ID: DTXSID50486259
• Nikkaji Number: J12.555E
• Wikidata: Q27266300
• Mol file: 483-54-5.mol

Synonyms:Aurantiogliocladin;483-54-5;2,3-dimethoxy-5,6-dimethylcyclohexa-2,5-diene-1,4-dione;2,3-DIMETHOXY-5,6-DIMETHYL-P-BENZOQUINONE;Aurantiogliocladin [MI];3,4-Dimethoxy-6-methyltoluquinone;2,3-Dimethyloxy-5,6-dimethylbenzoquinone;74R18PLB3Z;2,5-Cyclohexadiene-1,4-dione, 2,3-dimethoxy-5,6-dimethyl-;UNII-74R18PLB3Z;SCHEMBL487583;CHEMBL2252961;DTXSID50486259;NOYQJVWDVBANHI-UHFFFAOYSA-N;AKOS006283563;FT-0693046;NS00011752;2,3-Dimethoxy-5,6-dimethylbenzo-1,4-quinone;Q27266300

Chemical Property of Aurantiogliocladin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 62.5°
• Boiling Point: 337.326°C at 760 mmHg
• Flash Point: 150.393°C
• PSA: 52.60000
• Density: 1.167g/cm³
• LogP: 0.97900
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 196.07355886
• Heavy Atom Count: 14
• Complexity: 326

Purity/Quality:

99%, ^*data from raw suppliers

2,3-Dimethoxy-5,6-dimethyl-p-benzoquinone ^*data from reagent suppliers

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)C

Technology Process of Aurantiogliocladin

There total 25 articles about Aurantiogliocladin 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: 62.0%

2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) + tert-butyl alcohol (75-65-0) → 2,3-dimethoxy-5,6-dimethyl-2,5-cyclohexadiene-1,4-dione (483-54-5)

Guidance literature:

With iron(III)-acetylacetonate; bis-[(trifluoroacetoxy)iodo]benzene; at 120 ℃; for 5h; Sealed tube; Green chemistry;

DOI:10.1055/s-0039-1690193

Reference yield: 53.0%

tert-Butyl peroxybenzoate (614-45-9) + 2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) → 2,3-dimethoxy-5,6-dimethyl-2,5-cyclohexadiene-1,4-dione (483-54-5)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100 ℃; for 2h; Sealed tube; Green chemistry;

DOI:10.1016/j.tet.2019.130729

Reference yield:

2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) + acetic acid (64-19-7,77671-22-8) → 2,3-dimethoxy-5,6-dimethyl-2,5-cyclohexadiene-1,4-dione (483-54-5)

Guidance literature:

With ammonium peroxydisulfate; silver nitrate; In water; acetonitrile; at 65 ℃; for 3.5h;

DOI:10.1016/j.tet.2011.06.026

upstream raw materials:

4-sulfobenzenediazonium

1,4-dihydroxy-2,3-dimethoxy-5,6-dimethylbenzene

diazomethane

2,3-dihydroxy-5,6-dimethyl-1,4-benzoquinone

Downstream raw materials:

1,4-dihydroxy-2,3-dimethoxy-5,6-dimethylbenzene

C₁₀H₁₂O₄^(2-)

1,2,3,4-tetramethoxy-5,6-dimethyl-benzene

tetramethoxy-phthalic acid

Refernces

• 1、 Cao, Shouhao,Ji, Hongfang,Jia, Rui,Ma, Zhiwei,Shen, Liang,Xu, Zhengbao. "Iron-Catalyzed Radical Methylation of Activated Alkenes with tert -Butanol as the Methyl Source". supporting information. p. 1909 - 1913. Retrieved 2019/09/30.
• 2、 Perri, Steven T.,Moore, Harold W.. "Rearrangements of cyclobutenones. Synthesis of benzoquinones from 4-alkenyl-4-hydroxycyclobutenones". . p. 1897 - 1905. Retrieved 2007/10/02.