diospyrin

Base Information

• Chemical Name: diospyrin
• CAS No.: 28164-57-0
• Deprecated CAS: 27939-56-6
• Molecular Formula: C₂₂H₁₄O₆
• Molecular Weight: 374.35
• NSC Number: 208730
• UNII: O0IQZ8B2R7
• DSSTox Substance ID: DTXSID30182429
• Nikkaji Number: J21.593G
• Wikidata: Q27106425
• ChEMBL ID: CHEMBL242550
• Mol file: 28164-57-0.mol

Synonyms:Diospyrin(7CI); Euclein; NSC 208730

Chemical Property of diospyrin

Chemical Property:

• Melting Point: 286.8℃
• Boiling Point: 732.3oC at 760 mmHg
• Flash Point: 410.6oC
• PSA: 108.74000
• Density: 1.513±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 3.11240
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 374.07903816
• Heavy Atom Count: 28
• Complexity: 808

Purity/Quality:

99%, ^*data from raw suppliers

DIOSPYRIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1)O)C(=O)C=C(C2=O)C3=C(C4=C(C=C3C)C(=O)C=CC4=O)O

Technology Process of diospyrin

There total 9 articles about diospyrin 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: 82.0%

5,5'-dimethoxy-7,7'-dimethyl-[2,6'-binaphthalene]-1,1',4,4'-tetraone (39093-14-6) → diospyrin (28164-57-0)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200004)2000:7<1313::AID-EJOC1313>3.0.CO;2-I

Reference yield:

2-bromo-5-methoxy-7-methyl-1,4-naphthoquinone (273200-84-3) → diospyrin (28164-57-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 53 percent / Na₂CO₃ / Pd(PPh₃)4 / ethanol; toluene; H₂O / 3 h / Heating

2: 100 percent / Ce(NH₄)2(NO₃)6 / H₂O; acetonitrile / 0.83 h / 0 - 20 °C

3: 82 percent / AlCl₃ / CH₂Cl₂ / 24 h / 20 °C

With aluminium trichloride; ammonium cerium(IV) nitrate; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; dichloromethane; water; toluene; acetonitrile; 1: Arylation / 2: Oxidation / 3: Demethylation;

DOI:10.1002/1099-0690(200004)2000:7<1313::AID-EJOC1313>3.0.CO;2-I

Reference yield:

2-bromo-1,5,8-trimethoxy-3-methylnaphthalene (189066-68-0) → diospyrin (28164-57-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / B(OMe)3; nBuLi / tetrahydrofuran; hexane / 12 h

2: 53 percent / Na₂CO₃ / Pd(PPh₃)4 / ethanol; toluene; H₂O / 3 h / Heating

3: 100 percent / Ce(NH₄)2(NO₃)6 / H₂O; acetonitrile / 0.83 h / 0 - 20 °C

4: 82 percent / AlCl₃ / CH₂Cl₂ / 24 h / 20 °C

With n-butyllithium; aluminium trichloride; ammonium cerium(IV) nitrate; Trimethyl borate; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 1: Substitution / 2: Arylation / 3: Oxidation / 4: Demethylation;

DOI:10.1002/1099-0690(200004)2000:7<1313::AID-EJOC1313>3.0.CO;2-I

upstream raw materials:

diosquinone

5,5'-dimethoxy-7,7'-dimethyl-[2,6'-binaphthalene]-1,1',4,4'-tetraone

2-bromo-1,5,8-trimethoxy-3-methylnaphthalene

2-bromo-5-methoxy-7-methyl-1,4-naphthoquinone

Refernces

• 1、 Pardhasaradhi,Krishnakumari. "". . p. 684. Retrieved 1979.
• 2、 Pullella, Glenn A.,Vuong, Daniel,Lacey, Ernest,Piggott, Matthew J.. "Total Synthesis of the Antitumor-Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer". supporting information. p. 3623 - 3634. Retrieved 2021/01/09.