Asterriquinone B1

Base Information

• Chemical Name: Asterriquinone B1
• CAS No.: 78708-35-7
• Molecular Formula: C₃₄H₃₄N₂O₄
• Molecular Weight: 534.655
• DSSTox Substance ID: DTXSID501101785
• Nikkaji Number: J353.464B
• Wikidata: Q75064468
• Metabolomics Workbench ID: 117407
• ChEMBL ID: CHEMBL18783
• Mol file: 78708-35-7.mol

Synonyms:asterriquinone B1

Chemical Property of Asterriquinone B1

Chemical Property:

• PSA: 84.18000
• LogP: 7.18850
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 534.25185757
• Heavy Atom Count: 40
• Complexity: 1130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C2C(=CC=C1)C(=CN2)C3=C(C(=O)C(=C(C3=O)OC)C4=C(NC5=CC=CC=C54)C(C)(C)C=C)OC)C

Technology Process of Asterriquinone B1

There total 16 articles about Asterriquinone B1 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione (78860-34-1) → asterriquinone B1 (78708-35-7)

Guidance literature:

In tetrahydrofuran; at 23 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(99)00965-X

Reference yield: 74.0%

methanol (67-56-1) + 2,5-dibromo-3-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-6-[7-(3-methylbut-2-enyl)-1H-indol-3-yl][1,4]benzoquinone (339094-45-0) → asterriquinone B1 (78708-35-7)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 4h;

DOI:10.7164/antibiotics.54.105

Reference yield: 33.0%

methanol (67-56-1) + 2,5-dichloro-3-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-6-[7-(3-methyl-but-2-enyl)-1H-indol-3-yl]-[1,4]benzoquinone (477883-70-8) → 2-chloro-6-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-5-methoxy-3-[7-(3-methyl-but-2-enyl)-1H-indol-3-yl]-[1,4]benzoquinone + 2-chloro-3-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-5-methoxy-6-[7-(3-methyl-but-2-enyl)-1H-indol-3-yl]-[1,4]benzoquinone (851229-21-5) + asterriquinone B1 (78708-35-7)

Guidance literature:

With potassium carbonate; for 0.5h; Heating;

DOI:10.1021/ja044325h

upstream raw materials:

diazomethane

2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione

methanol

2,5-dichloro-3-[2-(1,1-dimethylallyl)-1H-indol-3-yl]-6-[7-(3-methyl-but-2-enyl)-1H-indol-3-yl]-[1,4]benzoquinone

Downstream raw materials:

2-[2-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-5-(4,4-dimethyl-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3,6-dihydroxy-[1,4]benzoquinone

2-[2-(1,1-dimethyl-2-propenyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methyl-2-butenyl)-1H-indol-3-yl]-2,5-cyclohexadiene-1,4-dione

2-[2-(1,1-Dimethyl-allyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-hydroxy-3-methyl-butyl)-1H-indol-3-yl]-[1,4]benzoquinone

Refernces

• 1、 Liu, Kun,Wood, Harold B.,Jones, A. Brian. "Total synthesis of asterriquinone B1". . p. 5119 - 5122. Retrieved 1999.
• 2、 Tatsuta,Mukai,Mitsumoto. "Short and convergent synthesis of asterriquinone B1 and demethylasterriquinone B1 [1]". . p. 105 - 108. Retrieved 2007/10/03.