anti-Benzo(h)quinoline-7,8-diol-9,10-epoxide

Base Information

• Chemical Name: anti-Benzo(h)quinoline-7,8-diol-9,10-epoxide
• CAS No.: 113163-22-7
• Molecular Formula: C₁₃H₁₁NO₃
• Molecular Weight: 229.235
• DSSTox Substance ID: DTXSID40921003
• Mol file: 113163-22-7.mol

Synonyms:CCRIS 2967;anti-Benzo(h)quinoline-7,8-diol-9,10-epoxide;113163-22-7;ANTI-BENZO[H]QUINOLINE-7,8-DIOL-9,10-EPOXIDE;Oxireno(3,4)benzo(1,2-h)quinoline-2,3-diol, 1a,2,3,9c-tetrahydro-, (1a-alpha,2-beta,3-alpha,9c-alpha)-;DTXSID40921003;LS-101108;1a,2,3,9c-Tetrahydro[1]benzoxireno[3,2-h]quinoline-2,3-diol

Chemical Property of anti-Benzo(h)quinoline-7,8-diol-9,10-epoxide

Chemical Property:

• Vapor Pressure: 8.14E-11mmHg at 25°C
• Boiling Point: 500°Cat760mmHg
• Flash Point: 256.2°C
• Density: 1.555g/cm³
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 229.07389321
• Heavy Atom Count: 17
• Complexity: 324

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C3=C(C=C2)C(C(C4C3O4)O)O)N=C1

Technology Process of anti-Benzo(h)quinoline-7,8-diol-9,10-epoxide

There total 8 articles about anti-Benzo(h)quinoline-7,8-diol-9,10-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: 69.0%

trans-7,8-dihydro-7,8-dihydroxybenzoquinoline (87707-10-6,113163-21-6) → 7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzoquinoline (113163-22-7,113216-90-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; for 48h; Ambient temperature;

DOI:10.1021/jo00241a044

Reference yield: 57.0%

Acetic acid (7S,8R)-8-acetoxy-9-bromo-10-hydroxy-7,8,9,10-tetrahydro-benzo[h]quinolin-7-yl ester (113163-27-2) → 7β,8α-dihydroxy-9β,10β-epoxy-7,8,9,10-tetrahydrobenzoquinoline (113163-22-7,113216-90-3)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 0 - 5 ℃; for 0.5h;

DOI:10.1021/jo00241a044

Reference yield:

7-hydroxy-benzoquinoline (87707-11-7) → 7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzoquinoline (113163-22-7,113216-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / adogen-464, potassium nitrodisulfanate in 1/6 M KH₂PO₄ (Fremy's salt) / benzene; H₂O / 1.5 h / Ambient temperature

2: 1.) KBH₄, air, 2.) pyridine / 1.) THF/EtOH, 22 h, 2.) 0 deg C, overnight

3: 78 percent / methanol, NH₃ / tetrahydrofuran / 48 h

4: 69 percent / m-chloroperoxybenzoic acid (MCPBA) / tetrahydrofuran / 48 h / Ambient temperature

With pyridine; methanol; potassium dihydrogenphosphate; potassium borohydride; air; potassium nitrososulfonate; Adogen-464; ammonia; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; water; benzene;

DOI:10.1021/jo00241a044

upstream raw materials:

trans-7,8-dihydro-7,8-dihydroxybenzoquinoline

7-hydroxy-benzoquinoline

benzoquinoline-7,8-dione

Acetic acid (7S,8S)-8-acetoxy-7,8-dihydro-benzo[h]quinolin-7-yl ester

Refernces