β₁-Citromycinon

Base Information

• Chemical Name: β₁-Citromycinon
• CAS No.: 79036-54-7
• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.359
• Mol file: 79036-54-7.mol

Synonyms:

Chemical Property of β₁-Citromycinon

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of β₁-Citromycinon

There total 30 articles about β₁-Citromycinon 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:

8-O-methylchrysophanol (3300-25-2) → (7S,8R)-8-Ethyl-1,7,8,11-tetrahydroxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione (79036-54-7,80926-99-4,81873-54-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) 1 N NaOH, sodium dithionite / 1) methanol; 2) 1 h, 5 deg C

2: 4.24 g / SOCl₂ / CH₂Cl₂ / 1 h

3: 97 percent / 0.2 N NaOC₂H₅ / dimethylformamide; ethanol / 1 h / Ambient temperature

4: 1 N NaOH / ethanol / 4 h

5: 0.33 h / 160 °C

6: 96 percent / trimethoxyorthoformiate, p-toluenesulfonic acid / benzene / 5 h / 50 °C

7: 94 percent / 4-(dimethylamino)pyridin / pyridine / 12 h

8: 70 percent / N-bromosuccinimide / CCl₄ / 0.5 h / 80 °C / Irradiation

9: 63 percent / Mg, ethyl dibromide 1,2- / tetrahydrofuran / 0.5 h

10: 92 percent / AlCl₃ / CH₂Cl₂ / 3 h

11: 80 percent / m-chlorobenzoic acid / CH₂Cl₂ / 5 h

12: 80 percent / acetic acid / 3 h / 80 °C

13: 4 percent / 0.5 N NaOH / 1 h

With dmap; sodium hydroxide; N-Bromosuccinimide; aluminium trichloride; thionyl chloride; sodium dithionite; sodium ethanolate; toluene-4-sulfonic acid; magnesium; ethylene dibromide; 3-chlorobenzoate; trimethyl orthoformate; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1002/jlac.198119811216

Reference yield:

8-O-methylchrysophanol (3300-25-2) → β1-Citromycinon (79036-54-7,80926-99-4,81873-54-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) 1 N NaOH, sodium dithionite / 1) methanol; 2) 1 h, 5 deg C

2: 4.24 g / SOCl₂ / CH₂Cl₂ / 1 h

3: 97 percent / 0.2 N NaOC₂H₅ / dimethylformamide; ethanol / 1 h / Ambient temperature

4: 1 N NaOH / ethanol / 4 h

5: 0.33 h / 160 °C

6: 96 percent / trimethoxyorthoformiate, p-toluenesulfonic acid / benzene / 5 h / 50 °C

7: 94 percent / 4-(dimethylamino)pyridin / pyridine / 12 h

8: 70 percent / N-bromosuccinimide / CCl₄ / 0.5 h / 80 °C / Irradiation

9: 63 percent / Mg, ethyl dibromide 1,2- / tetrahydrofuran / 0.5 h

10: 92 percent / AlCl₃ / CH₂Cl₂ / 3 h

11: 80 percent / m-chlorobenzoic acid / CH₂Cl₂ / 5 h

12: 80 percent / acetic acid / 3 h / 80 °C

13: 0.5 N NaOH / 1 h

With dmap; sodium hydroxide; N-Bromosuccinimide; aluminium trichloride; thionyl chloride; sodium dithionite; sodium ethanolate; toluene-4-sulfonic acid; magnesium; ethylene dibromide; 3-chlorobenzoate; trimethyl orthoformate; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1002/jlac.198119811216

Reference yield:

2-Chlormethyl-1-hydroxy-8-methoxy-3-methyl-9,10-anthrachinon (77825-01-5) → (7S,8R)-8-Ethyl-1,7,8,11-tetrahydroxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione (79036-54-7,80926-99-4,81873-54-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 97 percent / 0.2 N NaOC₂H₅ / dimethylformamide; ethanol / 1 h / Ambient temperature

2: 1 N NaOH / ethanol / 4 h

3: 0.33 h / 160 °C

4: 96 percent / trimethoxyorthoformiate, p-toluenesulfonic acid / benzene / 5 h / 50 °C

5: 94 percent / 4-(dimethylamino)pyridin / pyridine / 12 h

6: 70 percent / N-bromosuccinimide / CCl₄ / 0.5 h / 80 °C / Irradiation

7: 63 percent / Mg, ethyl dibromide 1,2- / tetrahydrofuran / 0.5 h

8: 92 percent / AlCl₃ / CH₂Cl₂ / 3 h

9: 80 percent / m-chlorobenzoic acid / CH₂Cl₂ / 5 h

10: 80 percent / acetic acid / 3 h / 80 °C

11: 4 percent / 0.5 N NaOH / 1 h

With dmap; sodium hydroxide; N-Bromosuccinimide; aluminium trichloride; sodium ethanolate; toluene-4-sulfonic acid; magnesium; ethylene dibromide; 3-chlorobenzoate; trimethyl orthoformate; In tetrahydrofuran; pyridine; tetrachloromethane; ethanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; benzene;

DOI:10.1002/jlac.198119811216

upstream raw materials:

β₁-Citromycinon-7-acetat

8-O-methylchrysophanol

2-Chlormethyl-1-hydroxy-8-methoxy-3-methyl-9,10-anthrachinon

9,10-dihydro-11-ethoxy-8-ethyl-1-hydroxy-5,12-naphthacenedione