4,7-Diphenyl-1,3-benzodioxole-5,6-dione

Base Information

• Chemical Name: 4,7-Diphenyl-1,3-benzodioxole-5,6-dione
• CAS No.: 7204-23-1
• Molecular Formula: C19H12O4
• Molecular Weight: 0
• DSSTox Substance ID: DTXSID20487435
• Nikkaji Number: J14.261A
• Wikidata: Q82329454
• Mol file: 7204-23-1.mol

Synonyms:4,7-Diphenyl-1,3-benzodioxole-5,6-dione;7204-23-1;SCHEMBL22157876;DTXSID20487435

Chemical Property of 4,7-Diphenyl-1,3-benzodioxole-5,6-dione

Chemical Property:

• PSA: 52.60000
• LogP: 2.96510
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 304.07355886
• Heavy Atom Count: 23
• Complexity: 535

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(C(=O)C(=O)C(=C2O1)C3=CC=CC=C3)C4=CC=CC=C4
• General Description: 4,7-Diphenyl-1,3-benzodioxole-5,6-dione (phlebiarubrone) is a naturally occurring terphenyl derivative synthesized from 2,5-diphenyl-1,4-benzoquinone. It serves as an intermediate in the chemical conversion to ustalic acid, a toxic compound found in *Tricholoma ustale*, though the yield of this transformation was low. 4,7-Diphenyl-1,3-benzodioxole-5,6-dione is part of a broader class of terphenyls and related structures studied for their synthetic accessibility and potential biological relevance.

Technology Process of 4,7-Diphenyl-1,3-benzodioxole-5,6-dione

There total 10 articles about 4,7-Diphenyl-1,3-benzodioxole-5,6-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: 100.0%

C20H14O4 (1040171-12-7) → 4,7-diphenyl-1,3-benzodioxol-5,6-dione (7204-23-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 0.05h;

DOI:10.1016/j.tet.2008.04.051

Reference yield: 59.0%

C22H18O4 (1040170-94-2) → 4,7-diphenyl-1,3-benzodioxol-5,6-dione (7204-23-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 100 ℃;

DOI:10.1016/j.tet.2008.04.051

Reference yield: 47.0%

C22H18O4 (1040170-94-2) → 4,7-diphenyl-1,3-benzodioxol-5,6-dione (7204-23-1) + C21H16O4 (1040171-01-4)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at -20 ℃; for 0.0833333h;

DOI:10.1016/j.tet.2008.04.051

upstream raw materials:

4,7-diphenylbenzo[d][1,3]dioxol-5-ol

4,7-diphenyl-5-benzyloxybenzo[d]-1,3-dioxole

2,5-diphenyl-p-benzoquinone

2',3',5'-triacetoxy-p-terphenyl

Refernces

Syntheses of naturally occurring terphenyls and related compounds

10.1271/bbb.60389

The research focuses on the synthesis of naturally occurring terphenyls and related compounds, such as terferol, its corresponding quinone, and phlebiarubrone, starting from 2,5-diphenyl-1,4-benzoquinone. The study explores the chemical conversion of phlebiarubrone to ustalic acid, a toxic compound isolated from the poisonous mushroom Tricholoma ustale, although the yield was poor. The study highlights the development of an efficient synthetic route for these compounds and provides insights into their potential biological activities.