3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

Base Information

Chemical Name:3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone
CAS No.:619300-88-8
Molecular Formula:C₂₅H₃₆O₆
Molecular Weight:432.557
Hs Code.:

Synonyms:3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

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Chemical Property of 3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

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Technology Process of 3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

There total 5 articles about 3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone 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: 50.0%

: 619300-86-6
(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethyl-α-(2,3,5,6-tetramethoxyphenyl)naphthalene-1-methanol acetate

: 69672-67-9
2-hydroxy-4-methoxy-3-{[(2S,4aS,8aS)-octahydro-2,5,5,8a-tetramethylnaphthalen-1(2H)-ylidene]methyl}cyclohexa-2,5-diene-1,4-dione

: 619300-88-8
3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

: 3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-2,5-dimethoxycyclohexa-2,4-diene-1,4-dione

Guidance literature:: With ammonium cerium(IV) nitrate; In N,N-dimethyl-formamide; acetonitrile; for 0.25h;
DOI:10.1002/hlca.200390158

Reference yield:

: 2441-46-5
1,2,4,5-tetramethoxybenzene

: 619300-88-8
3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi; tetramethylethylenediamine / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 85 percent / tetrahydrofuran; hexane / 0.5 h

2.1: 94 percent / H₂ / Pd/C / methanol; ethyl acetate / 2 h

3.1: 78 percent / DMAP; pyridine / 4 h / Heating

4.1: 50 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; dimethylformamide / 0.25 h

With pyridine; dmap; n-butyllithium; ammonium cerium(IV) nitrate; N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/hlca.200390158

Reference yield:

: 155551-30-7
(1S,4aS,8aS)-3H-2-methylene-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene-1-carboxaldehyde

: 619300-88-8
3-{(acetyloxy)[(1S,2S,4aS,8aS)-decahydro-2,5,5,8a-tetramethynaphthalen-1-yl]methyl}-4,5-dimethoxycyclohexa-1,2-benzoquinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi; tetramethylethylenediamine / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 85 percent / tetrahydrofuran; hexane / 0.5 h

2.1: 94 percent / H₂ / Pd/C / methanol; ethyl acetate / 2 h

3.1: 78 percent / DMAP; pyridine / 4 h / Heating

4.1: 50 percent / Ce(NH₄)2(NO₃)6 / acetonitrile; dimethylformamide / 0.25 h

With pyridine; dmap; n-butyllithium; ammonium cerium(IV) nitrate; N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/hlca.200390158