9,10-Anthracenedione, 1-(acetyloxy)-8-hydroxy-

Base Information

• Chemical Name: 9,10-Anthracenedione, 1-(acetyloxy)-8-hydroxy-
• CAS No.: 43101-75-3
• Molecular Formula: C16H10O5
• Molecular Weight: 282.252
• DSSTox Substance ID: DTXSID40481516
• Wikidata: Q82316972
• Mol file: 43101-75-3.mol

Synonyms:9,10-Anthracenedione, 1-(acetyloxy)-8-hydroxy-;43101-75-3;(8-hydroxy-9,10-dioxoanthracen-1-yl) acetate;SCHEMBL9538649;DTXSID40481516;8-hydroxy-9,10-dioxo-9,10-dihydro-1-anthracenyl acetate

Chemical Property of 9,10-Anthracenedione, 1-(acetyloxy)-8-hydroxy-

Chemical Property:

• PSA: 80.67000
• LogP: 2.09290
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 282.05282342
• Heavy Atom Count: 21
• Complexity: 471

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1=CC=CC2=C1C(=O)C3=C(C2=O)C=CC=C3O

Technology Process of 9,10-Anthracenedione, 1-(acetyloxy)-8-hydroxy-

There total 1 articles about 9,10-Anthracenedione, 1-(acetyloxy)-8-hydroxy- 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:

3-hydroxy-2-pyrone (496-64-0) + juglone acetate (5196-28-1) → 9,10-dihydro-8-hydroxy-9,10-dioxoanthracen-1-yl acetate (43101-75-3) + 5-Acetoxy-1-hydroxy-anthrachinon (52869-26-8)

Guidance literature:

With triethylamine; In toluene; for 1h; Title compound not separated from byproducts; Heating;

DOI:10.1055/s-2005-922769

Reference yield:

9,10-dihydro-8-hydroxy-9,10-dioxoanthracen-1-yl acetate (43101-75-3) → 1-hydroxy-8-methoxy-2-(1'-oxo-2'-phenylthiopentyl)anthraquinone (92811-05-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) K₂CO₃ 2) HCl aq. (10percent) / 1) acetone, 70 deg C, 8 h 2) room temp.

2: 87 percent / triphenylphosphine, diethyl-azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature

3: 87 percent / sodium dithionite / dimethylformamide; H₂O / 1) 70 deg C, 1 h 2) room temp., 1 h

4: RhCl₃*3H₂O / ethanol / 10 h / Heating

5: 93 percent / K₂CO₃ / acetone / 10 h / Heating

6: 79 percent / N-bromosuccinimide / acetone; H₂O / 0 °C

7: 94 percent / Jones reagent / acetone / Ambient temperature

8: 1) AlCl₃ / 1) CH₂Cl₂, overnight 2) overnight, HCl aq., THF

9: 90 percent / NaOH, cetyltrimethylammonium bromide / benzene; H₂O / 2.17 h

With hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; aluminium trichloride; sodium dithionite; jones reagent; cetyltrimethylammonim bromide; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; rhodium(III) chloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)91538-8

Reference yield:

9,10-dihydro-8-hydroxy-9,10-dioxoanthracen-1-yl acetate (43101-75-3) → 1-hydroxy-8-methoxy-2-(1-oxo-2-sulfoxophenylpentyl)anthraquinone (95636-48-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) K₂CO₃ 2) HCl aq. (10percent) / 1) acetone, 70 deg C, 8 h 2) room temp.

2: 87 percent / triphenylphosphine, diethyl-azodicarboxylate / tetrahydrofuran / 1 h / Ambient temperature

3: 87 percent / sodium dithionite / dimethylformamide; H₂O / 1) 70 deg C, 1 h 2) room temp., 1 h

4: RhCl₃*3H₂O / ethanol / 10 h / Heating

5: 93 percent / K₂CO₃ / acetone / 10 h / Heating

6: 79 percent / N-bromosuccinimide / acetone; H₂O / 0 °C

7: 94 percent / Jones reagent / acetone / Ambient temperature

8: 1) AlCl₃ / 1) CH₂Cl₂, overnight 2) overnight, HCl aq., THF

9: 90 percent / NaOH, cetyltrimethylammonium bromide / benzene; H₂O / 2.17 h

10: 85 percent / sodium metaperiodate / acetic acid; H₂O / Ambient temperature

With hydrogenchloride; sodium hydroxide; sodium periodate; N-Bromosuccinimide; aluminium trichloride; sodium dithionite; jones reagent; cetyltrimethylammonim bromide; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; rhodium(III) chloride; In tetrahydrofuran; ethanol; water; acetic acid; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)91538-8

upstream raw materials:

3-hydroxy-2-pyrone

juglone acetate

Downstream raw materials:

1-hydroxy-8-methoxyanthraquinone

1-Acetoxy-8-methoxy-9,10-anthrachinon

8-acetoxy-1-benzoyloxy-2-iodoanthraquinone

8-acetoxy-2-benzoylethynyl-1-benzoyloxyanthraquinone