6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione

Base Information

Chemical Name:6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione
CAS No.:639064-76-9
Molecular Formula:C₁₉H₁₆O₅
Molecular Weight:324.333
Hs Code.:

Synonyms:

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Chemical Property of 6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione

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Technology Process of 6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione

There total 7 articles about 6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-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:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 639064-73-6
3-bromo-4a,8,9-trimethoxy-4aH-dibenzofuran-2-one

: 639064-76-9
6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione

Guidance literature:: cyclopenta-1,3-diene; 3-bromo-4a,8,9-trimethoxy-4aH-dibenzofuran-2-one; In toluene; at 23 ℃;

With lithium tetrafluoroborate; In water; acetonitrile;

With triethylamine; In dichloromethane;
DOI:10.1016/j.tetlet.2003.09.214

Reference yield:

: 132-64-9,214827-48-2
dibenzofuran

: 639064-76-9
6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione

Guidance literature:: Multi-step reaction with 12 steps

1.1: AlCl₃ / CH₂Cl₂ / 0 - 23 °C

2.1: m-CPBA / CH₂Cl₂ / 50 °C

2.2: 67 percent / DIBAL / CH₂Cl₂ / -78 °C

3.1: iPr₂NEt / dimethylformamide / 0 - 23 °C

4.1: n-BuLi; TMEDA / diethyl ether / -10 °C

5.1: m-CPBA / CH₂Cl₂ / 23 °C

5.2: K₂CO₃ / methanol

5.3: 69 percent / K₂CO₃ / acetone

6.1: HCl / methanol / 40 °C

7.1: 58 percent / imidazole; DMAP / dimethylformamide

8.1: K₂CO₃ / acetone

9.1: TBAF / tetrahydrofuran / 0 °C

10.1: Bu₄NBr₃ / CH₂Cl₂; methanol

11.1: 69 percent / PhI(OAc)2 / 0 °C

12.1: toluene / 23 °C

12.2: LiBF₄ / acetonitrile; H₂O

12.3: Et₃N / CH₂Cl₂

With 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; aluminium trichloride; N,N,N,N,-tetramethylethylenediamine; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; tetra-N-butylammonium tribromide; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Friedel-Crafts acylation / 2.1: Baeyer-Villiger oxidation / 12.1: Diels-Alder addition;
DOI:10.1016/j.tetlet.2003.09.214

Reference yield:

: 639064-71-4
8,9-dimethoxy-dibenzofuran-2-ol

: 639064-76-9
6-(6-hydroxy-2,3-dimethoxy-phenyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-dione

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₄NBr₃ / CH₂Cl₂; methanol

2.1: 69 percent / PhI(OAc)2 / 0 °C

3.1: toluene / 23 °C

3.2: LiBF₄ / acetonitrile; H₂O

3.3: Et₃N / CH₂Cl₂

With [bis(acetoxy)iodo]benzene; tetra-N-butylammonium tribromide; In methanol; dichloromethane; toluene; 3.1: Diels-Alder addition;
DOI:10.1016/j.tetlet.2003.09.214