4-epi-vulgarin

Base Information

• Chemical Name: 4-epi-vulgarin
• CAS No.: 132185-41-2
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 132185-41-2.mol

Synonyms:

Chemical Property of 4-epi-vulgarin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-epi-vulgarin

There total 15 articles about 4-epi-vulgarin 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: 9.0%

deoxyvulgarin (3650-22-4,7715-90-4,92655-45-3) → 11,13-dihydrodouglanin (7715-89-1,16886-42-3,95723-46-9,126642-74-8,139906-54-0) + vulgarin (2615-39-6,3162-56-9,16981-98-9,66289-87-0,132185-40-1,132185-41-2,1351-48-0,17237-80-8,34319-09-0)

Guidance literature:

With Aspergillus ochraceous; In ethanol; for 30h;

DOI:10.1039/P19870000471

Reference yield:

6-epi-α-Santonin (1618-78-6) → 6β-vulgarin (132185-41-2,1351-48-0,17237-80-8,34319-09-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 6 percent / H₂ / Pt-charcoal / CH₂Cl₂ / 5 h / 3800 Torr

2: 61 percent / Br₂ / CCl₄; CHCl₃ / 0.17 h / Ambient temperature

3: 94 percent / Li₂CO₃, LiBr / dimethylformamide / 1.25 h / 120 °C

4: 57 percent / 30percent H₂O₂, Na₂CO₃ / H₂O; tetrahydrofuran / 2 h / 35 - 40 °C

5: 28 percent / 100percent hydrazine hydrate / tetrahydrofuran / 0.08 h / Heating

6: 98 percent / Jones reagent / acetone / 0 °C

7: 7.5 percent / ethanol / 144 h / Rhizopus nigricans cultures

8: 1) Zn, acetic acid, 2) MCPBA / 1) reflux, 20 min, 2) H₂CCl₂, rt, 48 h

With jones reagent; hydrogen; dihydrogen peroxide; bromine; lithium carbonate; sodium carbonate; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium bromide; zinc; platinum on activated charcoal; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)87881-9

Reference yield:

santonin (481-06-1) → 6β-vulgarin (132185-41-2,1351-48-0,17237-80-8,34319-09-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 60 percent / 5percent HCl / dimethylformamide / 3 h / 85 °C

2: 6 percent / H₂ / Pt-charcoal / CH₂Cl₂ / 5 h / 3800 Torr

3: 61 percent / Br₂ / CCl₄; CHCl₃ / 0.17 h / Ambient temperature

4: 94 percent / Li₂CO₃, LiBr / dimethylformamide / 1.25 h / 120 °C

5: 57 percent / 30percent H₂O₂, Na₂CO₃ / H₂O; tetrahydrofuran / 2 h / 35 - 40 °C

6: 28 percent / 100percent hydrazine hydrate / tetrahydrofuran / 0.08 h / Heating

7: 98 percent / Jones reagent / acetone / 0 °C

8: 7.5 percent / ethanol / 144 h / Rhizopus nigricans cultures

9: 1) Zn, acetic acid, 2) MCPBA / 1) reflux, 20 min, 2) H₂CCl₂, rt, 48 h

With hydrogenchloride; jones reagent; hydrogen; dihydrogen peroxide; bromine; lithium carbonate; sodium carbonate; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium bromide; zinc; platinum on activated charcoal; In tetrahydrofuran; tetrachloromethane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)87881-9

upstream raw materials:

4-epi-6β-vulgarin

1α-hydroxy-5,6αH,4,11βH-eudesm-2-en-6,12-olide

11,13-dihydro-6β-tuberiferin

2α-bromo-3-oxo-5,6αH,4,11βH-eudesman-6,12-olide