anti-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(f)quinoline N-oxide

Base Information

• Chemical Name: anti-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(f)quinoline N-oxide
• CAS No.: 119478-49-8
• Molecular Formula: C₁₃H₁₁NO₄
• Molecular Weight: 245.235
• Mol file: 119478-49-8.mol

Synonyms:anti-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(f)quinoline N-oxide;119478-49-8

Chemical Property of anti-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(f)quinoline N-oxide

Chemical Property:

• Vapor Pressure: 1.75E-13mmHg at 25°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 245.06880783
• Heavy Atom Count: 18
• Complexity: 352

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(C=CC3=C2C4C(O4)C(C3O)O)[N+](=C1)[O-]

Technology Process of anti-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(f)quinoline N-oxide

There total 4 articles about anti-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(f)quinoline N-oxide 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: 85.7%

trans-7,8-dihydroxy-7,8-dihydrobenzoquinoline (103620-26-4,114416-29-4,87707-06-0) → (+/-)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzoquinoline 4-oxide (103620-27-5,119478-49-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 25 ℃; for 24h;

DOI:10.1021/jo00368a001

Reference yield:

trans-7,8-dihydroxy-7,8-dihydrobenzoquinoline (103620-26-4,114416-29-4,87707-06-0) → (7S,8S)-4-Oxy-7,8-dihydro-benzo[f]quinoline-7,8-diol + (+/-)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzoquinoline 4-oxide (103620-27-5,119478-49-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 25 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1021/jo00368a001

Reference yield:

trans-7,8-diacetoxy-7,8-dihydrobenzoquinoline (103639-19-6) → (+/-)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzoquinoline 4-oxide (103620-27-5,119478-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 29.5 percent / 2percent NaOH / methanol / 0.25 h

2: m-chloroperoxybenzoic acid / tetrahydrofuran / 4 h / 25 °C

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

DOI:10.1021/jo00368a001

upstream raw materials:

trans-7,8-dihydroxy-7,8-dihydrobenzoquinoline

trans-7,8-diacetoxy-7,8-dihydrobenzoquinoline

Acetic acid (7S,8S)-8-acetoxy-10-bromo-7,8,9,10-tetrahydro-benzo[f]quinolin-7-yl ester

Refernces