Dbade

Base Information

• Chemical Name: Dbade
• CAS No.: 70951-81-4
• Molecular Formula: C₂₂H₁₆O₃
• Molecular Weight: 328.367
• DSSTox Substance ID: DTXSID60991243
• Nikkaji Number: J413.618G
• Wikidata: Q82980943
• Mol file: 70951-81-4.mol

Synonyms:DB(a,h)A-3,4-diol 1,2-oxide;DBA 3,4-diol 1,2-oxide;DBADE;dibenz(a,h)anthracene-3,4-diol 1,2-oxide;dibenz(a,h)anthracene-3,4-diol 1,2-oxide, (1a alpha,2 alpha,3 beta,13c alpha)-isomer;dibenz(a,h)anthracene-3,4-diol-1,2-epoxide

Chemical Property of Dbade

Chemical Property:

• Vapor Pressure: 1.56E-17mmHg at 25°C
• Boiling Point: 645.3°C at 760 mmHg
• Flash Point: 344.1°C
• PSA: 52.99000
• Density: 1.476g/cm³
• LogP: 3.99400
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 328.109944368
• Heavy Atom Count: 25
• Complexity: 535

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2C=C4C=CC5=C(C4=C3)C6C(O6)C(C5O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC3=C2C=C4C=CC5=C(C4=C3)[C@@H]6[C@@H](O6)[C@H]([C@@H]5O)O

Technology Process of Dbade

There total 6 articles about Dbade 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: 85.0%

trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene (66267-19-4) → trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrodibenzanthracene (70951-81-4,86541-62-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1021/jo01292a007

Reference yield:

trans-3,4-bis(benzoyloxy)-1,2,3,4-tetrahydrodibenzanthracene (72378-84-8) → trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrodibenzanthracene (70951-81-4,86541-62-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NBS, benzoyl peroxide / CCl₄ / 1 h / Heating

2: DBN / tetrahydrofuran / 3.5 h / 4 °C

3: 53 percent / sodium methoxide / tetrahydrofuran; methanol / 0.25 h / Heating

4: 85 percent / m-chloroperbenzoic acid / tetrahydrofuran / 1.5 h / Ambient temperature

With N-Bromosuccinimide; Perbenzoic acid; 2,6-dichloro-benzonitrile; sodium methylate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; tetrachloromethane;

DOI:10.1021/jo01292a007

Reference yield:

trans-3,4-bis(benzoyloxy)-3,4-dihydrodibenzanthracene (72378-81-5) → trans-3,4-dihydroxy-anti-1,2-epoxy-1,2,3,4-tetrahydrodibenzanthracene (70951-81-4,86541-62-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / sodium methoxide / tetrahydrofuran; methanol / 0.25 h / Heating

2: 85 percent / m-chloroperbenzoic acid / tetrahydrofuran / 1.5 h / Ambient temperature

With sodium methylate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol;

DOI:10.1021/jo01292a007

upstream raw materials:

trans-3,4-dihydroxy-3,4-dihydrodibenzanthracene

7,14-dihydrodibenz[a,h]anthracene

1,4,7,8,11,14-Hexahydrodibenzanthracene

trans-3,4-bis(benzoyloxy)-1,2,3,4-tetrahydrodibenzanthracene

Refernces

• 1、 Lee, Hong Mee,Harvey, Ronald G.. "Synthesis of Biologically Active Metabolites of Dibenzanthracene". . p. 588 - 592. Retrieved 2007/10/02.