2-(5,5-dimethyltetrahydrofuran-2-yl)-5,8-dihydroxynaphthalene-1,4-dione

Base Information

• Chemical Name: 2-(5,5-dimethyltetrahydrofuran-2-yl)-5,8-dihydroxynaphthalene-1,4-dione
• CAS No.: 64981-70-0
• Molecular Formula: C16H16O5
• Molecular Weight: 288.2952
• Mol file: 64981-70-0.mol

Synonyms:

Chemical Property of 2-(5,5-dimethyltetrahydrofuran-2-yl)-5,8-dihydroxynaphthalene-1,4-dione

Chemical Property:

• Vapor Pressure: 7.3E-12mmHg at 25°C
• Boiling Point: 530.3°Cat760mmHg
• Flash Point: 200.9°C
• Density: 1.377g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(5,5-dimethyltetrahydrofuran-2-yl)-5,8-dihydroxynaphthalene-1,4-dione

There total 16 articles about 2-(5,5-dimethyltetrahydrofuran-2-yl)-5,8-dihydroxynaphthalene-1,4-dione 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: 80.0%

2-[1-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-pentyl]-5,8-dihydroxy-[1,4]naphthoquinone → cycloshikonin (64981-70-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 25 ℃; for 0.5h;

DOI:10.1016/S0960-894X(99)00457-6

Reference yield:

5,8-dimethoxytetralone (1015-55-0) → cycloshikonin (64981-70-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-Bu₄NBr₃ / CHCl₃; methanol / 3 h / 20 °C

1.2: 54 percent / CaCO₃ / dimethylformamide / 2 h / 150 - 160 °C

2.1: EtMgBr / diethyl ether

2.2: 70 percent / CH₂Cl₂ / 7 h / 0 °C / ultrasonication

3.1: 100 percent / imidazole / dimethylformamide / 24 h / 25 °C

4.1: 90 percent / DMAP; pyridine / 24 h / 0 - 25 °C

5.1: FeCl₃*SiO₂ / CHCl₃ / 5 h / 25 °C

5.2: aq. NaIO₄; silica gel / CH₂Cl₂ / 3 h / 25 °C

6.1: CH₂Cl₂ / 24 h / 25 °C

7.1: 100 percent / H₂ / 10 percent Pd/C / ethyl acetate / 16 h / 25 °C

8.1: diethyl ether / 3 h / 0 - 25 °C

9.1: NH₂NH₂*H₂O / methanol / 4 h / 25 °C

10.1: 85 percent / DAIB / acetonitrile; H₂O / 2 h / 0 - 25 °C

11.1: 70 percent / AgO; HNO₃ / acetonitrile / 0.5 h / 0 - 25 °C

12.1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 - 25 °C

With pyridine; 1H-imidazole; dmap; silver(II) oxide; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; ethylmagnesium bromide; hydrogen; nitric acid; tetra-N-butylammonium tribromide; silica gel; iron(III) chloride; hydrazine hydrate; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Substitution / 1.2: Dehalogenation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: Condensation / 4.1: Acetylation / 5.1: Hydrolysis / 5.2: Oxidation / 6.1: Substitution / 7.1: Hydrogenation / 8.1: Grignard reaction / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Hydrolysis / 12.1: Cyclization;

DOI:10.1016/S0960-894X(99)00457-6

Reference yield:

4-(2,5-dimethoxyphenyl)butyric acid (1083-11-0) → cycloshikonin (64981-70-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 85 percent / (CF₃CO)2O / CH₂Cl₂ / 4 h / 0 - 25 °C

2.1: n-Bu₄NBr₃ / CHCl₃; methanol / 3 h / 20 °C

2.2: 54 percent / CaCO₃ / dimethylformamide / 2 h / 150 - 160 °C

3.1: EtMgBr / diethyl ether

3.2: 70 percent / CH₂Cl₂ / 7 h / 0 °C / ultrasonication

4.1: 100 percent / imidazole / dimethylformamide / 24 h / 25 °C

5.1: 90 percent / DMAP; pyridine / 24 h / 0 - 25 °C

6.1: FeCl₃*SiO₂ / CHCl₃ / 5 h / 25 °C

6.2: aq. NaIO₄; silica gel / CH₂Cl₂ / 3 h / 25 °C

7.1: CH₂Cl₂ / 24 h / 25 °C

8.1: 100 percent / H₂ / 10 percent Pd/C / ethyl acetate / 16 h / 25 °C

9.1: diethyl ether / 3 h / 0 - 25 °C

10.1: NH₂NH₂*H₂O / methanol / 4 h / 25 °C

11.1: 85 percent / DAIB / acetonitrile; H₂O / 2 h / 0 - 25 °C

12.1: 70 percent / AgO; HNO₃ / acetonitrile / 0.5 h / 0 - 25 °C

13.1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 - 25 °C

With pyridine; 1H-imidazole; dmap; silver(II) oxide; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; ethylmagnesium bromide; hydrogen; nitric acid; tetra-N-butylammonium tribromide; silica gel; iron(III) chloride; hydrazine hydrate; trifluoroacetic anhydride; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Cyclization / 2.1: Substitution / 2.2: Dehalogenation / 3.1: Metallation / 3.2: Grignard reaction / 4.1: Condensation / 5.1: Acetylation / 6.1: Hydrolysis / 6.2: Oxidation / 7.1: Substitution / 8.1: Hydrogenation / 9.1: Grignard reaction / 10.1: Hydrolysis / 11.1: Oxidation / 12.1: Hydrolysis / 13.1: Cyclization;

DOI:10.1016/S0960-894X(99)00457-6

upstream raw materials:

shikonin

5,8-dimethoxytetralone

4-(2,5-dimethoxyphenyl)butyric acid

3-(2,5-dimethoxybenzoyl)propionic acid