3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate

Base Information

• Chemical Name: 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate
• CAS No.: 709640-13-1
• Molecular Formula: C₃₀H₂₄O₁₀
• Molecular Weight: 544.515
• Mol file: 709640-13-1.mol

Synonyms:3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate

Chemical Property of 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate

There total 9 articles about 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate 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: 47.0%

(S)-acetylmandelic acid (7322-88-5) + (+/-)-9-acetyl-6,7,9,11-tetrahydroxy-7,8,9,10-tetrahydronaphthacen-5,12-dione (60660-75-5,60733-78-0,63268-39-3,65877-42-1,70005-90-2,70005-91-3,74606-73-8,84773-46-6,58924-49-5) → 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate (709640-13-1) + 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenylethanoate (709640-12-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1081/SCC-120030758

Reference yield:

1,4-dimethoxybezene (150-78-7) → 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate (709640-13-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 17 percent / AlCl₃ / CH₂Cl₂ / 4 h / 20 °C

2: 88 percent / triethylsilane; CF₃COOH / 0.5 h / 0 °C

3: 81 percent / tetrahydrofuran / 2 h / 0 °C

4: 85 percent / O₂; t-BuOK; P(OEt)3 / dimethylformamide / 1 h / -15 - -10 °C

5: 87 percent / AlCl₃ / nitrobenzene / 0 °C

6: 95 percent / p-TsOH / benzene / Heating

7: NBS; AIBN / CCl₄ / 0.5 h / Heating; irradiation

8: 0.11 g / aq. HCl / dioxane / 1 h / 80 °C

9: 40 percent / DMAP; DCC / CH₂Cl₂ / 15 h / 20 °C

With hydrogenchloride; triethylsilane; dmap; N-Bromosuccinimide; aluminium trichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; oxygen; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; triethyl phosphite; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; nitrobenzene; N,N-dimethyl-formamide; benzene; 1: Friedel-Crafts condensation;

DOI:10.1081/SCC-120030758

Reference yield:

1-(5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-1-ethanone (33654-68-1,110881-09-9) → 3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl 2-(acetyloxy)-2-phenyl ethanoate (709640-13-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / O₂; t-BuOK; P(OEt)3 / dimethylformamide / 1 h / -15 - -10 °C

2: 87 percent / AlCl₃ / nitrobenzene / 0 °C

3: 95 percent / p-TsOH / benzene / Heating

4: NBS; AIBN / CCl₄ / 0.5 h / Heating; irradiation

5: 0.11 g / aq. HCl / dioxane / 1 h / 80 °C

6: 40 percent / DMAP; DCC / CH₂Cl₂ / 15 h / 20 °C

With hydrogenchloride; dmap; N-Bromosuccinimide; aluminium trichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; oxygen; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; triethyl phosphite; In 1,4-dioxane; tetrachloromethane; dichloromethane; nitrobenzene; N,N-dimethyl-formamide; benzene;

DOI:10.1081/SCC-120030758

upstream raw materials:

(S)-acetylmandelic acid

(+/-)-9-acetyl-6,7,9,11-tetrahydroxy-7,8,9,10-tetrahydronaphthacen-5,12-dione

2-acetyl-1,2,3,4,6,11-hexahydro-5,12-dihydroxynaphthacene-6,11-quinone

1-(5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenyl)-1-ethanone

Refernces