Dibenz(a,h)acridine 3,4-diol-1,2-epoxide

Base Information

• Chemical Name: Dibenz(a,h)acridine 3,4-diol-1,2-epoxide
• CAS No.: 125276-72-4
• Molecular Formula: C₂₁H₁₅NO₃
• Molecular Weight: 329.355
• Mol file: 125276-72-4.mol

Synonyms:Dibenz(a,h)acridine 3,4-diol-1,2-epoxide;Benz(h)oxireno(5,6)benz(1,2-a)acridine-2,3-diol, 1a,2,3,13c-tetrahydro-, (1a-alpha,2-beta,3-alpha,13c-alpha)-(+-)-;(+/-)-anti-Dibenz(a,h)acridine 3,4-diol-1,2-epoxide;125276-72-4

Chemical Property of Dibenz(a,h)acridine 3,4-diol-1,2-epoxide

Chemical Property:

• Vapor Pressure: 3.42E-18mmHg at 25°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 329.10519334
• Heavy Atom Count: 25
• Complexity: 541

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC4=C(C=CC5=C4C6C(O6)C(C5O)O)N=C32
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC3=CC4=C(C=CC5=C4[C@@H]6[C@@H](O6)[C@H]([C@@H]5O)O)N=C32

Technology Process of Dibenz(a,h)acridine 3,4-diol-1,2-epoxide

There total 7 articles about Dibenz(a,h)acridine 3,4-diol-1,2-epoxide 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: 67.0%

trans-3,4-dihydroxy-3,4-dihydrodibenzacridine (102421-84-1) → 3α,4β-dihydroxy-1α,2α-epoxy-1,2,3,4-tetrahydrodibenzacridine (102421-85-2,102491-85-0,125276-71-3,125276-72-4)

Guidance literature:

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

DOI:10.1021/jo00363a008

Reference yield: 67.0%

2α-bromo-1β,3α,4β-trihydroxy-1,2,3,4-tetrahydrodibenzacridine (102421-86-3) → 3α,4β-dihydroxy-1β,2β-epoxy-1,2,3,4-tetrahydrodibenzacridine (102421-85-2,102491-85-0,125276-71-3,125276-72-4)

Guidance literature:

With Amberlite-400; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00363a008

Reference yield:

trans-3,4-dihydroxy-3,4-dihydrodibenzacridine (102421-84-1) → 3α,4β-dihydroxy-1β,2β-epoxy-1,2,3,4-tetrahydrodibenzacridine (102421-85-2,102491-85-0,125276-71-3,125276-72-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / H₂O, N-bromoacetamide (NBA), 4 N HCl / tetrahydrofuran / 0.5 h / 0 - 5 °C

2: 67 percent / Amberlite-400 / tetrahydrofuran / 2 h / Ambient temperature

With hydrogenchloride; Amberlite-400; water; N-bromoacetamide; In tetrahydrofuran;

DOI:10.1021/jo00363a008

upstream raw materials:

trans-3,4-dihydroxy-3,4-dihydrodibenzacridine

trans-3,4-diacetoxy-3,4-dihydrodibenzacridine

1-bromo-3α,4β-diacetoxy-1,2,3,4-tetrahydrodibenzacridine

2α-bromo-1β,3α,4β-trihydroxy-1,2,3,4-tetrahydrodibenzacridine

Refernces