2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione

Base Information

• Chemical Name: 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione
• CAS No.: 60924-75-6
• Molecular Formula: C34H34N2O4
• Molecular Weight: 534.64
• Mol file: 60924-75-6.mol

Synonyms:2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione;asterriquinone dimethyl ether;2,5-dimethoxy-3,6-bis[1-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione;2,5-bis[1-(1,1-dimethylallyl)-1H-indol-3-yl]-3,6-dimethoxy-1,4-benzoquinone;asterriquinone A1;2,5-bis-[1-(1,1-dimethyl-allyl)-indol-3-yl]-3,6-dimethoxy-[1,4]benzoquinone;Asterrichinon-dimethylether;

Chemical Property of 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione

Chemical Property:

• PSA: 62.46000
• LogP: 7.00520

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione

There total 10 articles about 2,5-Bis[1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dimethoxy-2,5-cyclohexadiene-1,4-dione 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:

2,5-bis<1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl>-3-acetoxy-6-hydroxy-2,5-cyclohexadiene-1,4-dione (160786-85-6) → asterriquinone dimethyl ether (60924-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether / 0.5 h

2: 5 percent aq. NaHCO₃ / ethanol / 80 °C

3: diethyl ether / 0.5 h

With sodium hydrogencarbonate; In diethyl ether; ethanol;

DOI:10.1248/cpb.46.1325

Reference yield:

asterriquinone (60696-52-8) → asterriquinone dimethyl ether (60924-75-6)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 0.5 h

2: 5 percent aq. NaHCO₃, pyridine / 0.03 h / 80 °C

3: diethyl ether / 0.5 h

4: 5 percent aq. NaHCO₃ / ethanol / 80 °C

5: diethyl ether / 0.5 h

With pyridine; sodium hydrogencarbonate; In diethyl ether; ethanol;

DOI:10.1248/cpb.46.1325

Reference yield:

Acetic acid 2,5-bis-[1-(1,1-dimethyl-allyl)-1H-indol-3-yl]-4-methoxy-3,6-dioxo-cyclohexa-1,4-dienyl ester (173348-60-2) → asterriquinone dimethyl ether (60924-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 5 percent aq. NaHCO₃ / ethanol / 80 °C

2: diethyl ether / 0.5 h

With sodium hydrogencarbonate; In diethyl ether; ethanol;

DOI:10.1248/cpb.46.1325

upstream raw materials:

diazomethane

asterriquinone

asterriquinone monomethyl ether

2,5-bis<1-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl>-3-acetoxy-6-hydroxy-2,5-cyclohexadiene-1,4-dione

Downstream raw materials:

didemethylasterriquinone D

2-[1-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-3,6-dihydroxy-5-(1H-indol-3-yl)-[1,4]benzoquinone

2,5-Dihydroxy-3-(1H-indol-3-yl)-6-[2-(3-methyl-but-2-enyl)-1H-indol-3-yl]-[1,4]benzoquinone

asterriquinone

Refernces

• 1、 Kaji, Akira,Kimura, Kengo,Teranishi, Masanori,Kiriyama, Noriki,Nomura, Masaaki,Miyamoto, Ken-Ichi. "Preparation and structure-activity relationships of novel asterriquinone derivatives". . p. 1325 - 1329. Retrieved 2007/10/03.
• 2、 Arai,Masuda,Kiriyama,et al.. "Metabolic products of Aspergillus terreus. IV. Metabolites of the strain IFO 8835. (2). The isolation and chemical structure of indolyl benzoquinone pigments". . p. 961 - 969. Retrieved 2007/10/02.